WTF with Marc Maron Podcast - Episode 660 - Brian Kiley / Brian Posehn

Episode Date: December 3, 2015

Comedian Brian Kiley has been writing for Conan O’Brien’s shows for more than 20 years. But prior to that, he and Marc were doing open mics in Boston, and Brian was living with Todd Barry. They revisit the good old days, and the bad ones too. Plus, Brian Posehn returns to the garage to talk about his leading role in the new movie Uncle Nick. Sign up here for WTF+ to get the full show archives and weekly bonus material! https://plus.acast.com/s/wtf-with-marc-maron-podcast. Hosted on Acast. See acast.com/privacy for more information.

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Along with your favorite restaurant food, alcohol, and other everyday essentials. Order Uber Eats now. For alcohol, you must be legal drinking age. Please enjoy responsibly. Product availability varies by region. See app for details. It's a night for the whole family. Be a part of Kids Night when the Toronto Rock take on the Colorado Mammoth

at a special 5 p.m. start time on Saturday, March 9th at First Ontario Centre in Hamilton. The first 5,000 fans in attendance will get a Dan Dawson bobblehead courtesy of Backley Construction. Punch your ticket to Kids Night on Saturday, March 9th at 5 p.m. in Rock City at torontorock.com. all right let's do this how are you what the fuckers what the fuck buddies what the fucksters what's happening i am mark maron this is wtf my podcast welcome to all who are listening thank you for coming on the show today brian kiley this is a comedian that i've known literally

since i started doing comedy the first time i did open mics, I think in college. Brian Kiley was there in Boston. He's been a writer on the Conan O'Brien Show since about the beginning of the Conan O'Brien Show. He's got a book out now. It's a novel, The Astounding Misadventures of Rory Collins. And you can get that where you get books. We're talking to him in a couple minutes. Brian Posehn is going to stop by because he's got a new movie out. We're going to talk to him a bit.

I'll tell you about the play in a minute because it was, I've been going to a lot of theater lately. Well, at least three plays in the last six months. And I love it. I just, there's an experience available in a theater, in a play, at a play, if it's good, that is unlike anything else. Like I'm immediately just ripped open just by virtue of being in a goddamn theater where people are about to take the stage. There's an expectation there. There's an excitement to it. There's risk. There's danger to some degree that actual humans are going to be occupying that space up there and

moving through something emotionally. I'm just always blown away. Now, obviously, bad theater experiences are bad. And the experience of that risk and that vulnerability can work against the actual experience that you're supposed to be having if it ain't working. But I went to see a show, The Humans, by a guy named Stephen Karam, and it was devastating. And this is the interesting thing about theater. I mean, I can tell you it was a great play, and I can tell you it was bleak in a lot of ways but uh incredibly human like bleak in the most human way possible and it all takes place in one long act hour and a half or so at a thanksgiving dinner and the stuff that was covered it was so like raw just the human relationships that were on that stage were so familiar the way they were set up and the way that it sort of moved through

these conversations there was a bleakness to it and this is everyday stuff really i i don't know if i would call it a tragedy because it was all sort of lifted by the fact that there was a family and there was humanity and there was humility and there was some humor. Like, I don't even know if it's uplifting, but I get uplifted by weird things. I mean, I thought that Shortcuts by Robert Altman was one of the most uplifting films ever made about people. So I thought it was uplifting in in the sort of persistence of these characters and how well defined they were in all their flaws and and and sort of what barely sort of held them together was was the humanity of it i don't

it's hard for me to even explain it but but it was pretty it was pretty amazing and i and i didn't really know uh it was directed by joe montello i think that's how you say his name he's done a lot of stuff the cast was reed bernie jane howdy shell casey beck sarah steel lauren klein and arian moed and uh it was just it was like a daughter who was moving in with her boyfriend in New York in Chinatown. It was the sister who was a gay woman who had recently broken up with her lover, her significant other. It was their parents and then the grandmother who has Alzheimer's and is just sort of mentally incapacitated throughout the show. throughout the show. And it's just sort of the evolution of the dialogue around that family,

around who they are and their own personal weaknesses and illnesses and what they endure. And there are funny parts, but it's definitely not a comedy, but it's powerful, man. It's bleak and beautiful. And the ending is completely theatrical and bizarre. I recommend it highly. I don't see enough young people when I go to the theater, and I think you should engage. I know we've all gotten very acclimated to seeing sketch or improv. That's the theatrical experience of the new generation. It's like, you go see an improv show, but to see a well-constructed play move through the emotions and the arc of a story, certainly in one setting, is pretty profound. But I guess the message I got is that I hang a lot of my analysis and thoughts around the idea that we're all terrified, existentially terrified of dying. And that's why a lot of our behavior is what it is. And that may be true,

but I don't know if it is as powerful as the existential fear of living. And I, look, I don't want to get all heavy because we've got a fun show here, you know, but I know there's some bad things in the world. There's some bad things in all of us but this this this play really sort of handles it well and floats you know there there is a a a sort of a buoyancy to the uh to the pain of this play it was it's called the humans and it's at the uh it's at the roundabout so if you're in the new york area i recommend it i'm becoming a champion of the theater so brian posain friend of the show friend of mine love him uh remember him when he started back in uh back in san francisco he he's got a new movie coming out it's exciting for him he's he's the lead in the movie it's

called uncle nick it's produced by documentary film legend earl morris and you can see it in theater starting tomorrow friday, December 4th. But right now, let's talk to the very funny Brian Posain about his new movie, Uncle Nick, and also about Mr. Show and about comedy and about maybe a little bit about his kid. Let's see how it goes. It's winter and you can get anything you need delivered with Uber Eats. Well, almost, almost anything. So, no, you can't get snowballs on Uber Eats. But meatballs, mozzarella balls, and arancini balls? Yes, we deliver those.

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To show your true heart is to risk your life. When I die here, you'll never leave Japan alive. FX's Shogun, a new original series streaming February 27th exclusively on Disney+. 18 plus subscription required. T's and C's apply. Let's make sure i do it right brian posain that's amazing it's right right yeah i let you get i let you do something else for 20 years or so posain yeah you always did poo and i never corrected you what's happening now outside of this movie we're about to talk about, what are you doing? I just got off the road.

You did for how many dates? Yesterday I was in D.C. How was it? Saturday I was in D.C. Arlington Draft House. Always fun. What'd you do? Four shows?

Five. Five shows. Yeah. It's nice. It's like a movie theater. It's tiered seating. It's great. Great crowds.

They can have a drink. Yes. But it's not a bar per se. And the people there are thrilled to have comedy there. And they're not all jaded. It's one of my favorite places to still play. Oh, that's great. Where else did you go?

There's a handful of places I still like going to. I was in another one before that. It was in Denver the week before. An Arlington Draft House? Oh. Yeah, the week before that I was in Denver. No, those are two great rooms. You must feel like a fucking rock star right now.

Yeah, those are great. Yeah, you're only as funny as your last shows, and my last shows were pretty good. Yeah, but in Denver, you almost feel like, there's something wrong. I'm doing so good. Yeah. I was sick.

Not phoning it in, because I don't phone it in when I'm sick, but when I wasn't on stage, I was sweating and coughing. And then I get on stage, and I powered through those sets, and those sets and you know right crushed yeah it's like electric in there you're like you got i'm not this funny let's just tone it down a little bit i don't want to fuck this up just so i feel like i'm at the proper level yeah when i'm in grand rapids or wherever else and how's the kid he's awesome man he's a six-year-old little person. Oh, really? Yeah. Funny little dude. Yeah? Went to his first show this year where I took him to see Weird Al. You did?

Yeah. How'd he like it? Loved it. Yeah? Is he wearing black concert tees? Sometimes, but you know what? He knows the bands. Like, if you went up to him and went, yeah, what ACDC song do you like? He'd tell you. Which one does he like? He likes a bunch of them. Old ones? Yeah, he's kind song do you like? He'd tell you. Which one does he like? He likes a bunch of them.

Old ones? Bon Scott? Yeah, he's kind of all over the place. We've done more work on, and now Rush is the latest thing. Why is Rush seeing this amazing resurgence? Well, I've loved Rush my whole life. I find. And he, I kind of kept it away from him.

Why? Well. Too much. It's a lot of stuff going on. I would always play the basics in the car. I started them off, I mean, with the idea of I don't want this kid to like pop music, and so far he doesn't. Right, right.

So a lot of ACDC. Okay. A lot of Black Sabbath. Yeah. Zeppelin. Yeah. Beatles. Yeah. He was born to the Beatles.

Okay. Good. Those are good choices. And that's kind of it for the beginning. Oh, and the Ramones. Okay. And then... He's got to like the Ramones.

My wife played the Cars for him a couple years ago. How'd that go? He got into the Cars. He really liked that. Yeah, it's good stuff. And so we're keeping a solid base. Uh-huh. And then now he knows

that Daddy likes these other bands almost more. Like Metallica? He knows that Rush, Metallica, Pantera. Uh-huh. So he asked me about those bands. And it's awesome. Like he's a little dude, but he knows that this is something that daddy

feels a lot of passion for. Sat him down with 2112? No, you know what I did is, he's into the Peanuts movie, and somebody on the internet took that old Rush song, Xanadu, and did it with the Peanuts from old specials. Oh, you're sneaking it in. And he loved it.

Right. And then I'm playing, I'm moving pictures one day, and he goes, it ends, and he goes, Daddy, I kind of want to hear Xanadu. Can you play Xanadu? That's my favorite Rush song. And I'm like, all right, man. Without the Peanuts.

Yeah, I can definitely play Xanadu for you. And he still dug it. Like, he dug it just listening. I have a nice turntable set up in our little library, and he and I it like he dug it just listening i have uh you know a nice turntable setup in our uh in our little library yeah and he and i will do legos in there and then it's always records playing spinning records while we're building that's sweet it's dude i couldn't love it more man it's my favorite part and and wait metallica you have not that much yet but he knows they're around i mean if they, if you're in my office,

if you walk out of my door, there's a picture of James Hetfield flipping everybody off. So he knows about them. It's a lot for me to wrap my head around. Metallica? Yeah. I was just, you know, I like him.

I had Trujillo in here last week to plug the Jocko movie. He's a great guy. Oh, wow, yeah. And he's played with Ozzy. He's a great guy, that Robert Trujillo. He's a really nice dude. You met him? Oh, yeah, yeah. Sweet guy, right? Yeah, yeah. I love great guy. Oh, wow, yeah. And he's played with Ozzy. He's a great guy, that Robert Turd. He's a really nice dude. You met him?

Oh, yeah, yeah. Sweet guy, right? Yeah, yeah. I love that guy. But I don't listen to a lot of Metallica. I almost bought a Metallica record today, except they didn't have any. They had a lot of Megadeth, which I can listen to Megadeth. A little more technical than Metallica's straight ahead and just more kick-ass.

I can feel the weight of it for you. Metallica is the thing, right? Yeah. Yeah, man. Well, really, it's Rush, Iron Maiden, and Metallica because they all made huge impacts on me when I was a kid. How about Iron Maiden? He must like those covers.

Iron Maiden. Oh, the kid? I haven't played much of that. He hears it like we have Sirius on when he's in the van. Yeah. And so it'll come on and Daddy will turn it up a little. And he can read. He's reading now.

So he'll read the whole thing and go, Daddy, this is Iron Maiden. Eddie, right? And I'm like, yeah, man. Eddie. Yeah, man. Is he playing an instrument? He is. He's playing the piano.

Really? And then we got him a little Squire. And I'm going to get him an amp for Christmas because he's been plugging into my amp just recently and loves it. He's got a band. He calls himself Organic Submarine. Wow. Interesting. He made that up. Not a metal name. No, not at all. But I just want my kid to be musical. I mean, that was really kind of important to me. Does he have a sense of it? You feel like he is? Absolutely.

Yeah, the piano teacher said he had a perfect pitch, and my wife can sing, and I can't do anything. Wow, it's all working out. It's going good. Yeah. When I'm home, those parts are awesome. I hope to God at 14 he doesn't decide, like, I'm playing football. Yeah, there's so many things.

Yeah, it's not even football. I don't hate sports, but there's other things. I think if he said, Daddy, I like Sublime, I'd be like, fuck you. Yeah, yeah, got to move out early. Yeah, stuff like that. Give me back the guitar. Yeah, or political things, too. If you went a certain way, that might piss me off a little more.

Well, that's going to take longer. A little more than being a jock. You know what I did to rebel? You can negotiate that stuff away. I rebelled against my mom in high school. As soon as I was able to vote, I voted for Reagan that year. Why? Because my mom was such a liberal.

How do you feel about that? Yes, Sonoma. I feel guilty. I mean, I'm telling you because I think it's funny. Yeah. Because it was kind of the high school dick of like, and I was this total metal kid trying to grow my hair. Yeah.

And I knew my mom would hate that I voted for Reagan, so I fucking did. Did you tell her? Absolutely, in her face. Like, came home with the I voted sticker. Like, yeah, you voted for the dude you hate. Suck it. Now, have you told this story before?

Is this confession? No, that's new. All right, so this is a confession? No one's ever heard that? Yeah, pretty much. And it's out. You have that way of getting that out of people. That's your big one.

That's a big one for me. It is big. But it was like rebelling against her, because against a liberal mom. I get it. She worked for the state. She hated Jerry Brown. She hated, you know. Real lefty.

Yeah, still is. And you were mad at her. I was. All right, well, you okay with her now? I love her. Yeah, she's awesome she's so how do you want to how do you want to make up for this mistake i think you're doing it already the kid sounds good you do good deeds in the world sure i'll send in her uh what do

they call the ballots where that where you're not there that her absentee yeah i'll send that in for trump well no no that would work that would make it worse it'd be make it worse how do i undo it yeah yeah how do you undo it i don't know so all right come clean to her this weekend when she's at my house well she knew that you said she does but i mean come tell her that i feel bad now yeah she knows i didn't give a shit about reagan right but now well but now like i think a lot of people are like, well, it's kind of your fault, Bri. Oh, yeah, that he got that second term. That was that one vote. It was a joke vote.

It was a fuck you vote. Right. All right, so you're a movie star now. Is that what's happening? No. Oh, come on. I'm trying to build it up. Thanks, man.

You're the lead. I am. The lead guy in a Christmas movie. In almost every single scene, yeah. Holy shit. So if you like that, if you like me, and you have an hour and a half of watching me. It's called Uncle Nick. Uncle Nick. How was the experience for you?

How long did it take to shoot? We pinged it out in a couple weeks, shot it in Pasadena. Two weeks? Yeah, it was total indie. Not much money. That's like total, total indie. Yeah, but we shot it in pasadena two weeks yeah it was what was total indie uh not much money yeah but we shot it in one house and kind of made it look like a couple different houses but it's really only it the whole movie takes place in one night uh-huh the whole story is i'm uncle nick uh my uh to this girl my brother who's a total douche i I hate him. What type of douche? Just pretty boy dick, just smug.

I took on the family business. Which is? And worked my ass off landscaping. And after my dad passed and my mom passed, I took over everything. He didn't do anything. He was a bartender. I really looked down on him and hate him and have all this animosity. And it was a lot of fun to play because I don't have any siblings, but it was fun to have. But you have the animosity.

Oh, yeah. I can be a total dick. So it was nice to channel that into somebody. And so he marries Padgett Brewster, our friend and hot lady. And she already has two kids. She has a 16-year-old son and a 20-year-old daughter, a 19-year-old daughter. And I get a crush on the daughter at the wedding.

And the whole time I'm thinking. Your step-niece. Yeah. So at Christmas, I'm going to make this shit happen. I've been talking to her on Facebook. It's super creepy. It starts off where, I don't know if I like this guy. And I love that.

Like reading that i was yeah that appealed to me more than anything that seems honest yes yeah yeah so without spoiling much uh does it end happily it does it has a good ending and it's earned i feel and there's funny moments and there's some shit where you find out what my character's gone through. I have this, you know, kind of drunk rant at the table and kind of, you know, some sadness about what my character went through. And it was one of the hardest things I've ever done. To perform it? Yeah, because I had to cry and I had to bring up some dark stuff.

Wow. It was a lot of fun, though. Really acting? I was, yeah, yeah. That's fucking great, dude. I did the whole thing. I got an acting coach. Yeah.

So how'd you get involved with this movie? Well, these guys wrote it together. This guy, Mike Dembski and Chris Kasich was going to direct it. And they were producing it together. It was Dembski's idea. And Chris wanted to direct a movie. And then really early on, they thought of me. And then, you know, Jerry Duggan, my buddy, who I wrote Deadpool with for years.

You've seen him in the scene. He's not a comedian, but he's been around. Did he write? Yeah, I know Jerry. Yeah, he's a writer, right? Yeah, he's more a writer. Now he's writing Deadpool on his own. He's a good friend of mine. And he talked to them

and said that he would produce it with them and try to get me to do it. And just a total posain, like they sent me the script. I didn't read it for a couple of weeks because I was just like, I don't know, you know. And he's like, dude,

and finally it took him just going, you asshole, they wrote this with you in mind, man. They really want you. It doesn't happen that often. Yeah, never. Yeah. And dude, do you think I didn't whine like every time one of my friends gets another

movie, you know? Here we go. And I'm like, you know what I mean? Patton's been handed another. I didn't say Patton. You motherfucker. But yeah, when Patton did Big Fan, you know, there was a little bit of like,

I want a big fan. Oh, sure, like Oscar thoughts about Patton. No! And then this comes up. It's on my computer for me to very easily read. Took me weeks. And it finally was Jerry going, you know, Jerry knows how to talk to me. He's like, don't be a fucking asshole.

Just read it. If you don't like it, read a couple pages and get back to me. Do this now. It's weird, that fundamental insecurity thing. Like, you know, because you want to do something like that, but there's that. For the last 10 years, I've been waiting for it. And then there's that initial instinct. It's like, it's probably not going to do it.

It's probably going to suck. Oh, yeah. And the whole time we were shooting it, I'm like, this is gonna blow. No joy. Yeah. Pose saying no joy. Right. Yeah.

But it was a great experience. It was. And I'm super proud of it. It's nice. The guy was in his first movie. Yeah. So everyone's learning. Everyone's very collaborative.

Yeah, for sure. Improvising a bit. And then we got to bring some funny people. I was involved in the casting like so i was the first person cast and then he was like who do you see as your sister and yeah we talked about that and we talked about another friend of ours as my sister didn't happen yeah and then missy pile came up it was actually my wife going what about missy pile and i'm going oh my god that's perfect. Like tall, she would be the attractive one

in the family, obviously. Yeah. But the guy playing my brother already is more attractive. Who's that guy? I'm the black sheep. This guy, Bo Ballinger, he's actually Chris's cousin.

Okay. But don't let that deter you. He killed it. Yeah, he did really good and he played, he's supposed to be, I'm unlikable, but he winds up being the biggest douche in the movie. Oh, man.

So, yeah, he did really well. So you're like an unlikable underdog guy that's not, wouldn't be likable in most contexts. Yes. But somehow compared to the situation. This other guy. And what happens. You'll see I won't give away some stuff that he does.

Your moral struggle. Yes. Yes. Yes. Yeah, for the first time ever. Not even in real life or movies have I had a moral struggle ever. Finally. Yeah. Finally.

And then Scott Adsit, we had come in and play my sister's husband. He's funny. He's all right. And he's terrible to be around. I don't know if you know him. He's such a dick. No, he's the nicest guy in the right. And he's terrible to be around. I don't know if you know him. He's such a dick. No, he's the nicest guy in the world. Yeah, yeah, yeah.

But you told me that Earl Morris produced it, the documentarian. He's an odd guy. How did he get involved? Because he knew Chris. Chris had done some documentary work for him before. And so they hooked up, and Chris, he wanted to see it. And it does have a through line of, are you a baseball guy at all?

No. I didn't know it, but I guess, so it takes place in Cleveland. Yeah. And I guess there's a famous Cleveland Indians game in the 70s or 60s maybe, where it was Tencent Beer Night. Uh-huh.

And it turned into a crazy riot. I think I know that. And so I tell, I narrate that story throughout, and it kind of intertwines with the story that I'm going through. Sounds like an interesting movie. It's cool, man. Well, I'm proud of you, man. I'm happy for you.

Thanks, buddy. Yeah, and let's talk about when does it open? December what? Fourth? December 4th and 5th, that weekend. It's doing some midnight shows in some cities. When does it drop on iTunes and everything else? Netflix?

I think almost right after, if not that same day, right after. It's wild how it all happens at the same time. Yeah. Just see the fucking movie. Right. I would say seeing it in a theater, I think it would be fun. And it's doing some midnight showings in some cities. Does it have the potential to

be like christmas cult movie i don't know all right i you know i don't like anything i do all right it was a bad question for you to pretend like something i'd love i but i'm always the last guy to fit you know to know unless it's stuff like other people's stuff where i've been involved i'm like oh this is awesome yeah yeah you know mr show sarah silverman those things i'm over here yeah yeah they're the main people yeah yeah yeah yeah well i hope i don't make this suck how is bob and david you guys seen him i just saw them the other day i posted a little thing with them uh the other day but uh they had a it seemed like everyone had good time we did man did, man. We had a blast. And, you know, fingers crossed.

I think it's, you know, I don't know how numbers work at Netflix and that kind of thing. Yeah. No one does. Yeah. Netflix doesn't know. They know. But hopefully they pick us up. And then we go back after Bob finishes Better Call Saul again.

Yeah. He's out there doing that right now. And then I want to do more because those are, you know, you know how I've talked to you about how I feel about both those guys. Yeah, yeah. They helped me out a lot. I mean, I owe everything really to them. Yeah. I mean, because stand up and all that other stuff.

I was doing it before, but that put me in this. That was it. Yeah. And they're good. It's still my favorite job, working for those two dudes. And was it good to see everybody? It absolutely was. And everyone's good. It's still my favorite job, looking for those two dudes. And was it good to see everybody? It absolutely was. And everyone's okay?

Yeah, man. Well, there's none of the... We're all grownups now. I know. There was a little bit of weirdness, but not like the old days. Sure. No pencils were thrown and no feet were stomped. Was Dino there too?

Yes. No shit. Yeah, of course. Yeah, yeah, he had. He has to be. Oh, that's crazy. Those guys love him and so do I. I got to watch those fucking things. I got to watch your movie. I got to watch... I got a, he has to be. Oh, that's crazy. Those guys love him, and so do I. I got to watch those fucking things.

I got to watch your movie. I got a lot of things to do. Trying to remember if Dino got on camera. I think he snuck on in one thing or two, but he's behind the scenes through the whole thing. Like that guy, yeah. Yeah. He wrote a thing with Scott Atz at that,

the cunt sketch. Oh, it was good? Yeah. We'll just call it that? You'll know what I mean. Okay. Well, great, man. Good luck with it, Brian. good? Yeah. We'll just call it that? You'll know what I mean. Okay. Well, great, man. Good luck with it, Brian.

Thanks, buddy. Brian Posehn, I wish him the best this Christmas season. I'm very excited that he got that part. It sounds like it was fun. He sounds great. I love talking to him. Now, we've got another Brian. This is the tale of two Brians today.

Brian Kiley, as I said, we started together. We genuinely, I mean, we were really doing open mics together. And I look like I've aged. He looks like he has not. This is actually a great conversation. I've always loved Brian a lot. He's always been a stand-up dude and a great stand-up comic. And it was great to have him in here.

I'm full of the greats today. I'm full of the greats today. I'm full of the greats today. His new novel, The Astounding Misadventures of Rory Collins, you can get anywhere, wherever you get books. But right now, we'll talk to novelist and Conan O'Brien writer and stand-up comedian Brian Kiley. What the fuck? What the fuck?

What the fuck? What the fuck? What the fuck? What the fuck? What the fuck? What the fuck? What the fuck? Kylie. Who's, like, what president biographies do you read? Well, I love, like, LBJ and I love Nixon. Oh, really? Partly because they're from my childhood, you know?

But also they're such characters, like, Truman and Ike and even JF whatever, they're still kind of normal guys. Those guys, you're like, well, no one would do that. Right, right. They both do shit, like in totally different ways, but they both do things where you're like, no one acts like that. Right. And I just love the way they're such characters, you know? Who, LBJ and Nixon? Yeah.

And they were on the opposite sides. Opposite sides. I guess that's right. They were part of our, how old are you? I'm 53. I'm going to be 52. Well, I'll be 54 in a month. Oh, really? So you're two years older than me. Yeah. But when we were kids, Nixon was everywhere. Everywhere. Cartoons. Absolutely. Yeah. Absolutely. I never found him... I think I was fascinated with him when I was

a kid, but I think it was kind of a morbid fascination. I don't remember finding him impressive. Oh, no, no. I'm not a fan, but I think it was kind of a morbid fascination. I don't remember finding him impressive. Oh, no, no. I'm not a fan, but I am fascinated by him. I remember caricatures more than I remember the actual guy. Sure, sure. Like Mad Magazine and just seeing the pictures of him with the big nose. Oh, yeah, yeah. Tricky dick.

So I always, in my mind, even when I was a little kid, he's like, you know, this guy's kind of slimy. Yeah. my mind even when i was a little kid he's like you know this guy's kind of slimy yeah well there was that there was a cartoon it was like a cartoon show called like wait till father gets home or something like that and the next door neighbor was nixon really yes and i remember seeing as a kid and thinking this is a really intellectual smart show and then i saw it when i was like in my 30s at the museum of television and it was incredibly bad really oh yeah i was like the museum of television yeah so when you lived in new york yeah you made i would go there i would yeah i went there frequently you did because well that's it well that's the interesting thing like

you you've been writing for conan since almost the beginning right yeah i started six months in. So, 94? Mm-hmm. That's amazing. Well, yeah. It's 94, so that's 20- March, March, the Ides of March in 1994. So, in 22 years, almost? Yeah, it'll be 22 years next March. That you've been a Conan writer? Yeah. Mostly monologue? Mm-hmm.

Yeah, I mean, I'll help out with the other stuff, but that's my main focus, yeah. And the thing is, we started together. Yes. Kind of. Right. Right. We really did. I mean, we've known each other, whatever, almost 30 years or whatever.

That's crazy. I know. I know. It's not like we went out to dinner or anything, but we've known each other. No, no, no. And we were always friendly and we did plenty of gigs together. Yeah. Of course we were friendly.

And softball and whatever. Softball in Boston with the fellas. Yeah. With, you know, waiting for Matt Graham to lose his shit. When's Matt Graham going to ruin the game? Well, it's interesting because you had a career. I mean, we were both doing, I think I met you at open mics. I must have been in college.

I think the first time I saw you was probably the first time I tried to do comedy, which was probably the summer of 1984, maybe. Yeah. Is that about when you started? Yeah, I started a little bit before that. And I remember seeing you at Sam's. That was it, the basement. Yes.

And you had this joke. I don't know if you're going to remember it. I probably will. But it was a joke about, you were talking about the Flemish artists. And you said, where is Flem? Do you remember that? I remember that. I always love jokes. I love great jokes. I don't know if I'm proud of this one.

I thought it was, I remember laughing at that and I remember thinking, oh, that's a great joke. But you know, you were always so... Aggravated? You were so comfortable on stage though. I was so envious of that. I was a nervous wreck and you were always very relaxed on stage from the very beginning i was faking it well you did a good job of faking it though you know because i think that i was i i think i was terrified and and when i get terrified i actually relax in a weird way yes when i get terrified i get this paralysis and i'm like i sort of surrender to it i i'm i was always so envious of that. And I didn't know you were like that until you and I were driving

to a gig one time in Rhode Island. Oh no. Which we were, right? It was like a military thing or something. Do you remember? Was it that one with the car in the middle of the room? No, that was in... I did that one in Connecticut, I think. There was one a couple hours out.

Yes, yes. And there was another one where it was near like a naval base or something and they would come right and i remember you were nervous and i was driving with you and it was like i remember being like you're nervous like i was always nervous you know what i mean but i was always like what are you worried about you know but i was probably opening for you well it, it was you, me, and Cy Bell. Cy Bell! Yeah. Did he pass? He did. Recently, right?

I did like a month or two ago. That's so bad. Yeah. He was great. He was great. What a character. Unbelievable. No one would believe that guy.

No, he's just always worked up and excited and happy. He would run the marathon and then do a 45-minute set that night. Like age 60. He was unbelievable. Oh, he was such a madman. He was. Didn't he call himself that? Like the madman of Revere?

Yeah. Where the fuck was he from? He was from Lynn. Lynn? Lynn, maybe. Where'd you grow up? I grew up in Newton. Oh, really?

Yeah. Oh, so that's not as provincial or weirdly regional. No, no. You're not from like uh yeah yeah because like the further out you get the accent gets a little difficult it's mine's gotten a little better since i've left yeah yeah yeah when i hear it like old tapes it's like oh my god but like uh which part the the the the rich part uh no i mean it was we were like a we were in a little bit over our heads in a sense. I think my dad got the house when I was three or four.

Yeah. So I don't know. I think there were rich people near us. Right, right, right. You guys were just hanging on. Yeah, yeah. Hanging on to the illusion. Yeah, absolutely. How many kids were in the family?

Five. So it was a big Irish Catholic kind of deal? Yeah, mm-hmm. I'm in the middle of five. Really? Yeah. Well, you got older brothers and kind of deal? Yeah. I'm in the middle of five. Really? Yeah. You got older brothers and sisters? Like brothers or sisters? I've got an older sister and a younger sister and an older brother and a younger brother. So I've got the complete set.

And everybody gets along still? Pretty much. I mean, there's some weird baggage, but we can actually get together at a family event and everyone goes, oh, everyone's fine. You know what I mean? Everyone's okay? Yeah. Both folks still alive? No. My mom died when i was 22 and my dad died a couple years ago oh sorry man yeah yeah so you got it so it's got to be the siblings now yeah that's all you got yeah and do all of them live in the boston area still uh just my younger sister my older sister

lives in san diego my uh older brother lives in fort lauderdale and my younger brother lives in phoenix oh wow everyone's spread out but a couple of them are kind of close yeah yeah well i always thought like when i when i used to see you i my first thought was like well there's kylie how the fuck is he in such good shape like i like i just pictured that you you did comedy and then it was pretty much the gym that was probably that was how i pictured it yeah i did do a lot of the gym in though especially in those days yeah like fucking ripped all the time it was like you and brian frazier what are those guys doing well i i don't know what frazier's deal but you know i i went bald when i was 22 you know i was like this freak you know so it's like i needed to do something you know how to compensate oh my god absolutely it was like I needed to do something, you know? Had to compensate? Oh, my God. Absolutely. It was like, you know, I'd go out and do my act and be like, this guy is 22.

You know what I mean? Like you hear murmuring in the crowd, you know? That's sad. Yeah. What a sad bald guy. I know. He's big, though. Be cool.

Don't fuck with him. I wouldn't make any jokes. But what did you do in high school? Were you a jock in high school? No. You know what? Well, I mean, I was on the baseball team, but I barely played. Baseball, right. Yeah, I barely played. or you're just they didn't put you in no they just

didn't put me you know it was like that kind of thing but you were a sports guy i that was my obsession yeah i love sports still yeah yeah and like my heroes are sports guys and stuff like who uh like bobby orr and yaz and and like b like that. Bobby Orr, the hockey player. Yaz Strimski, the baseball player. And those are the big ones when you were growing up? Yeah. Did you get to meet them? I did get Yaz's autograph, but just like in a pile of kids kind of thing.

Pile of kids holding balls? Yeah, yeah, that kind of thing. Balls hanging out. There's a ball. Sign it. Sign my ball. It was one of those? Yeah.

Well, what was it about that? What was it about Yaz? See, I don't know anything about that because I don't have it. Sign my ball. It was one of those? Yeah. Well, what was it about that? What was it about Yaz? I don't know anything about that because I don't have that part of my soul. Yeah, but I have to say, though, you were always a good softball player. I remember being surprised. Oh, right, yeah. You know, just because you weren't a sports guy. Let's see what the fucking druggie does.

Well, that's just it. You were never the guy that you'd talk about the game when you'd go to the gig or whatever. You know what I mean? But you could play, and I was like, oh and everyone's like like anthony clark was good and i was like oh i wouldn't know you know what i mean like like there are players that you didn't think you know right you weren't expecting because they never talked about sports well i think that i'm physically uh you know i have ability right i can do shit right and also we're talking comedian level do you know what i level but there were a couple of you guys

but you were the guy that would get up and just be like I'm not going to get in front of that ball whatever that guy fucking hammers out here you were able to hit it properly you get up there and hit a ball and that's how a guy really hits well those were fun days though

didn't you have cleats? I think you had cleats no no I didn't do that I didn't want to do that there were guys with cleats? I think you had cleats. No, no, I didn't do that. I didn't do that. No, no, I didn't want to do that. I projected that? Yeah. There were guys with cleats, but I was not one of the cleat kids, guys. Well, that's the funny thing about what people think about comedians.

And in a lot of the comics I talk to, I think the only time we really talk about sports on this show in terms of us doing it was Gary Shandling had a fairly famous basketball game that people would play you know the guys around here but always had this sort of air of kind of like you got to play in the shandling game like it was still a networking thing but back then when we were in boston we'd all meet at that fucking field yeah there'd be different levels of hangovers going on oh yeah there'd be different levels you know some people were smoking weed but it was like that was like 1989 maybe 88 yeah probably 88 89 and we'd all just go all this like all these gypsies and weirdos it was fun it was fun and it was interesting and there was even some sort of culture clash in a sense so like there were certain comics that they worked the nicks and

they didn't work at catch but they yeah you know what i mean so it was kind of like i know who they are yeah yeah because like i was one of these for whatever reason and you were as well um we could work both places yes and we it was sort of surprising that i could it was like when i really think back on on the type of comedy i was doing at that time for the type of audience i was doing it for, I was like, I must have had some balls I never knew existed. Because we'd go to those fucking one-nighters. Oh, my God. And I'd be like, angry Jewish man. And then they take it somehow.

I did all right. But I could work at Nick's. Yeah. Yeah. And I found if you had a joke that worked at Nick's, which was downtown, and then you had a joke that worked in Cambridge, which was very PC there was PC right then you to me then you had something you know but you were always like uh like jokes yeah it wasn't like you're gonna be like you know let's talk for a second I know I wish I'm I I that's true I just said I would go have my little jokes and then I'd

go that's all I got but you were so diligent you're such a joke writer which is completely different than the than the way I work right oh yeah absolutely and i don't think there's many guys that do it as specifically as you like you know you write jokes yeah yeah like and you do it for a living now but uh in terms of like having doing monologue jokes but but back then like let's go back to softball let's see i can try and remember the game i remember i hit dave crossing the eye with a ball once and and that was a bad day. We weren't even playing yet. We were just warming up.

And you just threw it? Yeah, we were just throwing it, and he wasn't paying attention. Oh, jeez. But it used to be like it was John Innes, me, you, Anthony Clark sometimes, Matt Graham, Dave Cross sometimes Bob Wilson Fred Wilson Yeah The Wilson Brothers Sure Simply Fred yeah

Yeah Bob's past Yeah R.I.P. Tony V sometimes Yeah Maybe Yeah But you went in

Let's see so So we're doing open mics In 84 85 Yeah I graduated In college 83 With what kind of degree English

Major Yeah You know Yeah And I started doing Open mics in college. What compelled you? You know, I wanted to be a comedy writer as a kid.

Really? That's interesting. Not a stand-up necessarily? Well, I wanted to be a stand-up, but I thought there was no way to do it. Do you know what I mean? It's funny, in those days, you never heard about anybody who was a comedian. There weren't any comedy clubs. It wasn't that kind of thing when I was growing up. Yeah. So, as much as I thought about it, I thought, well, that's not practical.

Yeah. So, I thought, but I did know, I knew shows had comedy writers. Right. I knew sitcoms had writers and stuff, and I would watch the Dick Van Dyke show i was like oh i'd like to do that you know yeah so i started writing jokes when i was like 13 or 14 and i really yeah i had like these little note cards and i would write my jokes and keep them in like a little like it's like a little recipe but like based on not watching stand-up but by watching by watching sitcoms primarily i? How did you know that people wrote jokes, per se? That's a good question.

I think, I guess I just knew comics did jokes, you know, and I would watch Rodney Dangerfield. Oh, yeah, Rodney Dangerfield, right. Yeah, you know. That's sort of the school that you come from. Yeah, yeah, I would say that, too. Yeah. So, and I would listen, there was a show on,

when I was a kid, there was a show on from Brookline Mass. This guy did it out of his house. This guy, Kenny Mayer, did it out of his house. A radio show? A radio show. Yeah. And he would play comedy albums.

He'd play like the whole side of an album. Right. And then he'd do his little commercials, like he'd talk and he'd have his sponsors. Yeah. And it would play half a Bob Newhart album or half a bill cosby album or whatever so that's where you got it and i would like list you know i'd be and i was supposed to be in bed asleep and i'd have my radio and i would be listening to these comedy and it was once a week it was like sunday night or something and that was when you were like 11 or 12 or something

i was probably like 15 or something then so that's where it went in yeah yeah i was i i love that stuff you know yeah yeah of course i mean it was so uh what it's such an amazing thing uh when we were able to laugh properly yeah that's true before we became all cynical and weird that's true and have to like like if it doesn't make us laugh we have to go like oh good joke that's good good tag that's. That's true. Good tag. Oh, boy. You know, my daughter gets so mad at me because I'll watch something with her and I never laugh. I just think, oh, that's funny. And she's, why are you laughing? It's like, no, no, it's good.

It's good. It's good. You have to understand it's my job. It's true. It's like I just, yeah. So do you still have those note cards? I don't. I'm sure the jokes were terrible.

Really? I imagine that they would be like, I wonder how you don't remember any of them. Well, I do remember there was, I remember seeing, actually that guy, Kenny Mayer had a column on the Boston Herald. Yeah. And there was a joke about, this is in 1976. So I guess I was 15. And I was turning 15. I remember there was a joke that Rich Little did about Ronald Reagan being an actor

and then Gerald Ford being a stuntman. Right. It was a joke. And I had written that same joke. Oh, yeah? And I remember him quoting this in the paper, like, what a great joke. And I remember thinking, hey, I wrote that as a 14-year-old kid. You know what I mean? It made me feel like, hey, I can – I remember him quoting this in the paper, like, what a great joke. And I remember thinking, hey, that is a 14-year-old kid. You know what I mean?

It made me feel like, hey, I can, I don't know. It just made me feel like maybe I could do this or something. So you really put stuff together like that. Yeah. It's a very specific, like, I remember when I did a pilot for Comedy Central and we were going to do a monologue. And we had, you know, come up with this wheel of topics that I was going to spontaneously write monologue jokes for because the structure of a monologue joke or a one-liner

is you introduce one thing and then another thing and then you twist it. Do you do a twist somehow, right? Sure, sure. Basically, kind of? Yeah, there's a lot of that, absolutely. I mean, there's sort of different formulas, but that's definitely one.

Yeah, but we had all these different things on there and we'd spin it twice to get the two topics and I have to, we pre-wrote a bunch of them formulas, but that's definitely one. But yeah, but we had like all these different things on there and we'd spin it twice to get the two topics and I have to, we pre-wrote a bunch of them. Sure, sure, of course. But there is definitely a method of writing jokes that eludes me completely. If my jokes have to happen, like the beats have to come as I'm talking. I can't write them down. Yeah, but you know what?

You have that thing. I mean, you did Conan, the old show, more than anyone, the old show more than anyone right it was like 35 times or something i think i've done a total all in about 50 something that's amazing and you would go and and it's you would have that and some of it was a conversation but some of it was just the illusion of a conversation you're doing a bit right because other people would do bits and there'd be some great stand-ups that they would do panel and all of a sudden they're talking about this tv commercial or something right and it's and it was so contrived that it just didn't right it worked over there doing stand-up right but it didn't work on the couch can't load it into conversation but you had that ability and my thing is it's they're just jokes you know i i i did 45 minutes

i did this i headlined this casino gig in Nevada just a couple weeks ago. How was it? It was pretty good. Yeah. I did 135 jokes. Wow. That's a lot of jokes. That's crazy.

It is. What, did you have a guy counting them? No, I just had to, you know, I had to go over all my stuff. It's like in LA, you do so many short sets. I'm like, I don't even know what my 45 minutes is. You know what I mean? I had to write everything out and it was that many jokes. That's kind of fascinating because if you think about people

that work in that style, that must be what an hour set looks like. Yeah. And how to string those together sounds like a chore to me. Well, it is. And it's hard to remember. You know, if you're not doing it a lot,

when I did my Comedy Central special half hour, you know, in 2006 or whatever, they have bullet points. They've got the teleprompter. Right. And I had 97 bullet points. And they or whatever, they have bullet points. They've got the teleprompter. Right. And I had 97 bullet points. And they're like, that's a record. I was like, well, I don't know what to tell you.

I wish I could have like three things, you know, just tell three stories and that's a half hour. Right. But you know, like all those jokes you've done on stage before. I mean, it's not like you still have to pace them out. Right. But you have a very set sort of tone in the way you do jokes. Sure.

It's slightly detached. I think if you didn't know you well at different points in your life, you'd think like, this guy seems a little crazy. But not in a sort of like outward way. Like there's something going on in there. This large, well-built bald man with a kind of detached tone is sort of frightening. Like, there were times where I remember, like, I was like, wow, I wonder what his personal life is like, that guy. Well, yeah, my stuff can get darker than people realize. No, definitely.

Yeah, yeah. But, like, to do 135, you said? Yeah. Like, at least I fall back. Like, when I look at a chunk of mine that's like 12 minutes it has it's sort of a conversation that makes sense right and leads into the next thing of course like i can't imagine trying to fucking line up 135 clean jokes at that yeah yeah i mean it's you're pretty clean um i try to be tv clean yeah absolutely yeah yeah who were the guys

when we were starting out up there that you liked working with and looked up to? Well, what happened was I went to Boston College, and I'm a sophomore at college, and they had a comedy show at my school. And the first two guys I didn't really care for, but Crimmins went on, and I thought, this guy's hilarious. Great jokes.

And I went, he just had great jokes, and he was just doing stand-up then. I mean, he wasn't political at all. And he was just doing regular stand-up, but really, really funny. Early on, yeah. And I went up to him and I was like, oh, you know, I want to be a comedy writer. I wrote the show. You know, I still had my jokes.

I mean, I didn't have them with me, but I still had them at home, you know. You've been writing since 15? Yeah. Yeah. So I had all these jokes and he was running the Ding Ho. So he invited me to his club and i met with him i brought my brought like 50 jokes that i touched for the end of the bidding ho no about yeah this is probably like 81 or 82 so he's going strong yeah yeah and he so he kind of critiqued my jokes or whatever

and he's like well you can't really make money in boston uh writing yeah you have to perform and i was like oh i could never do, it was too scary for me. So he's like, well, whenever you want to come to the Ding Ho. So I would go to the Ding Ho like once a month. He would let me in for free

and I would just sit at the bar. And you were underage. I was underage, yeah. And I would sit at the bar and watch the comic. And I had to take like two subways and a bus. Like Inman Square was like-

From Newton? From Newton. Yeah. It was just, you know, I had to take the green line to the red line and then I had to take a bus to get to Emerson.

To Somerville, yeah. So, but I would go to the shows a lot and then I took a summer school class taught by Dennis Leary. Really? And it was... Long-haired Dennis Leary when he had the braid?

He didn't have the braid, but he, yeah, he was... And it was, you know, coming from Boston College, you know, some of you teachers are Jesuits, you know, and then you, it was, you know, coming from Boston College, we, you know, some of you teachers are Jesuits, you know? And then you come here and like the last, like someone would smoke pot in class or whatever,

you know? I was like, what the, you know what I mean? Like it was just such a, like. Where was he teaching that? At the adult education? At Emerson. Oh, Emerson, right. At their summer school thing or whatever.

Yeah. So. So you took a summer class in comedy writing? It was comedy writing and they had us do standup. In the class? In the class. So you took a summer class in comedy writing? It was comedy writing, and they had us do stand-up. In the class? In the class. And so I do the show, and then they were kind of like, oh, well, you should keep doing this or whatever.

Because you did it in class? Because I did it in class. What was that like for you? Was it a small class? Oh, yeah, yeah. Wasn't that scary? There's like six people, but the last class we could bring people in or whatever. So there's like, that probably were 20 people or something.

Was it nerve-wracking? Oh, yeah, yeah. But it was exciting, you know? And then they were they were like oh you should continue with this or whatever so i went to the ding ho the next week and i signed up for the open mic and crimens was the host so i so i did that and it went great and crimens gave me a great intro and all give me a good spot and all that stuff and then the next week i went back it was lenny and i'm on at one it was just horrible just like totally tanked it and it was you know he's like good try you know and i had some friends that came to the first one they're like holy shit that was amazing yeah and they came the next week like oh fuck this is the real reality of it you know so that was the beginning

that was the up and down yeah you got both but you were you were hooked i guess i was yeah i mean i i really yeah it was so exciting back then i was so filled with dread yes about going on because you know you wouldn't be able to go on every week and sometimes you'd wait weeks to do your five minutes or whatever and like you know by the time you know you just spend all that time going like oh god i gotta do it oh yeah and then like like there was that one night where i just sat there all night and he forgot to put me on because he got shit faced and you know i was sort of like i i had to say something but i was you know secretly relieved in a way oh that happened you know lenny one time the same thing happened to me he forgot to put me on yeah the show went and i was so like oh thank

god you know even though i'm here i was totally felt that but i remember he came up to me at the end thing though is it go ahead oh it's totally I remember he came up to me at the end that's a weird thing though go ahead oh it's totally weird well he came up to me at the end he said listen oh no you know what it was

I went back the next week yeah and the list was full for some reason they had capped it at certain people right so he goes

why aren't you on the list and I said well they said it was full fuck it you got fucked last week I'll put you on you do your five fucking minutes you get the fuck out of here

and whatever he just said this. Whatever. So the next morning. Nice to hear you cuss, Brian. Well, it's just funny. He just said this like that. So the next morning.

And you get out of here like he had to add that part. And get the fuck out of here. Get the fuck out of here. Yeah. So the next morning, my friend calls me. And I didn't realize that my mother had picked up the other end. And he's like, well, what happened? He goes, why?

And I just told him exactly what Lenny said. He said, fuck it. You got fucked last week. Get the fuck on. Do your five your five but get the fuck out that's how lenny talked yeah so my mother's overhearing all this or whatever and she's so my friend she's like what she comes to me what is this shit and funk out of you like she couldn't say fuck right right right but she was like appalled just to hear i was like i was quoting this other guy wow so you grew up in a house that was really kind of like oh yeah yeah yeah no cuss oh you didn't hear yeah yeah no neither one of them huh

no i mean my dad would driving once in a while but right but you never heard fucks like right oh yeah fucks are rare yeah in that in your household yeah yeah mine too i guess but that's it's a funny thing though that that we choose to do this thing that in and at the beginning like there's there's there's no excitement about it it's just a compulsion that needs to be that needs to be honored because like the idea that like the bigger relief would be like i didn't get up i know and you're pissed about it you have to act pissed yeah because you are and party's pissed but also you're so relieved right but it's kind of weird right sure think like god damn it i was so ready yes i'm gonna do it but no that's not it you're like oh god i hope the guy before me doesn't you know you know kill too hard oh oh all that stuff and i

remember i would lenny had this show on wednesday nights yeah and on tuesday at noon i would get a knot my stomach for like a day and a half. Right. And I remember one time, I'm in school, and it had been a Monday holiday. So I'm in school, I'm having lunch,

and I get the knot in my stomach, and I thought, today's Monday. Yeah. And then it's like, oh, no, no, it is Tuesday. Like my body knew to have the knot,

you know what I mean? Even though I was like off a day, you know? That's crazy. And then did we do, what was your big break that finally got you working? Did you do the riot? Were you in the riots with me? No, you was like off a day, you know? That's crazy. And then did we do, what was your big break that finally got you working? Did you do the riot? Were you in the riots with me?

No, you know what? I didn't do the riot. I think I was, I think I just, I just missed it or I wasn't around when the first one happened or something. Who gave you the first gig? Was it Barry, Mike, or The Connection? There was this guy. Or Nion? There was this guy. Or Nix. There was this guy.

Somebody saw me at the Ding Ho. He had a show, and it was called Sydney's on Green Street in Jamaica Plain. And it was this little dive, and this guy did it. And it was almost like old-fashioned show business. He had a couple guys in the band behind him, and's this club and jp with there's probably 10 people there and he would go up and i just the only joke i remember he would say to one guy make sure you're performing you're up here with him because otherwise he's playing by himself that was his joke yeah and he must have said it three times three or four times right and it didn't really work any of the times but it's like i remember thinking you know you really

shouldn't do the same joke in the same set like four times. Yeah, yeah. But that, he was supposed to give me 10 bucks and he gave me 15. Like he was just trying to be this like nice older guy or whatever. So that was my first real paid gig. But then the thing, oh, they would have me, they'd have me come in on a Saturday and just do five. Right.

And they'd give me 10 bucks or 20 bucks. What was the structure of the show on Saturday? Was four guys or three guys yeah it would be like four guys and if those guys would be all be doing 25 minutes and then they'd have like a five minute guest right for me and I remember maybe it was three guys but I remember my first one I come in I'm in the they were doing shows in both rooms on Saturdays and the acts were probably Barry and Lenny and who was around and Kevin Meaney was around and Rodgerson.

And DJ Hazard. DJ Hazard. Yeah, Stephen, I think he had kind of popped already by then. But that was back when DJ Hazard was just DJ Hanard. Yes, that's true. And he had not become the pirate character.

That's true. He would occasionally wear dark sunglasses on stage. He had no facial hair. No, you saw people develop their personas. Yeah, yeah. become the pirate character that's true he would occasionally wear dark sunglasses on stage yeah had no no facial hair no you saw people develop their personas yeah yeah yeah yeah and he played guitar through most of it oh yeah he he would do stand-up but then he was with big influence on louis actually seriously yeah i think ron lynch and dj you know yeah i think louis copped to that oh that's interesting you can definitely see see Ron Lynch in Louie. Yeah. Early Louie.

Yeah. Like, if you really think about early Louie when it was just, you know, sound effects and weirdness. Yes. Yeah, I could see that. Yeah, yeah. That's interesting. Well, no, I think what he got from DJ was that largeness for no reason. Yes, that's true.

I wouldn't have put that together. That's so interesting. Yeah. But I remember my first ding-ho, do my five minutes. I do my five minutes. I do my five minutes. It goes fine, blah, blah, blah. I'm in the back, and I'm standing next to Bob Batchelder. Bob Batch!

Yes. He was a great guy. So I'm standing next to him. He had- He used to close with the signs. He'd close with the signs, which would kill. Right. So he comes from-

He drove up from Kentucky. Yeah. He had been up all night or whatever. Yeah. He's going to go on next. He has an epileptic seizure. No. Right next to me.

Collapsing and, you know. Because he'd been up all night. Because up all night. And he had epilepsy. So, I called. You know, they come and they get the ambulance and they put him on the. So, they're like, well, you've got to go on to the next room and you've got to do 20. Because he's not on the show.

Clearly not happening. And I don't have 20. And I'm also just totally freaked out that this guy just had this, you know what I mean? Like I almost caught him when he felt like it was like that kind of thing. Like he's staying next to me and collapsed.

And they're like, all right, go next there. So I went on and did, I did 15 or 12. I have no recollection of what I saw. I must've just been like in shock. That was the baptism. Yes. That was it.

What was your your what's your batch story i've told it before oh okay he would just uh would he did he snap yeah yeah yeah he was such a great guy too but he would snap but he had this killer bit with the signs well that was the funny thing is right it was the whole the whole thrust of the story was that uh yeah we drove to that gig that one that was way down in like new Britain or somewhere, that one that was near another Naval base in Connecticut. It was like a Barry one night or a half a car. Yeah.

All right. Yeah. So, you know, in the whole way down, he's like, I don't know how to fucking get on Letterman. You know,

like, why is everyone getting, you know, how do I, you know, like just a few sure bitter. So I go do my 25 is right when I was starting out and it was about all i had 25 30 i did everything i had and i go to the bathroom and i come out and batches on stage basically

yelling at the audience the same thing he was saying in the car you don't think i want to be on letterman you know like and it was bad you know it was just like in each 10 minutes in it's a nightmare and there's nine people in the place and you know and in my recollection there was someone in a wheelchair and he's yelling and and And I've never done this again, but I literally, because the audience was so small, I said, hey, hey, hey, hey, hey, let's just take a breather. It was like I was a referee. Sure, sure. And I'm like, let's just chill out.

And then Bob does, and everything calms down. He's like, what am I going to do now? And I'm like, do the signs. Do the signs. And the signs would kill. They kill oh my god there was a few guys that snapped you don't see it anymore it doesn't really happen anymore but it was something we all knew about because it's not in the vernacular anymore because people they don't really i don't know if it's because there were so many comics there was more professionalism but but seeing people snap when we were coming up oh sure not

it was it happened oh yeah yeah like and it was a beautiful amazing, but seeing people snap when we were coming up. Oh, sure. It happened. Oh, yeah. And it was a beautiful, amazing thing. It was suddenly, the show is ruined. Like, the show is just ruined, you know? And there's always that thing of people that... Jay Charbonneau was a first top-rate snapper. And it is that thing. I always picture people who would...

They've been hearing a lot about stand up comedy and there's comedy clubs opening they haven't been and they go there for a show and they just see someone who can just lose their shit

and yeah it was so amazing I'm trying to think of something like Barry would do it a lot yeah but he always it seemed like he had a reason he could snap though

and get them back right which was which was miraculous yeah he was one of the few people most people once they snap, that's it. Yeah, it's over.

But he could somehow, not always, but he could often win them back, which was incredible. And how does, because Smigel is the original head writer, and how do you get that job on the first year of Conan? get that job on the first year of conan well you know i it's i had um you know i always wanted to do johnny carson so that was my whole thing was and i was trying to did you get on carson no i got on i got on leno like a year after carson's left so i did leno twice and i guess conan saw me on one of those actually well i'll tell you you. So then Louie's working at Conan. Yeah.

And Tom Agnes is working at Conan. And Chuck Sklar is working at Conan. Boston guy. Yeah. So somebody gets canned. So they need another, somebody else to write his monologue. Yeah. So I just send in stuff.

And at the time, I used to do a lot of topical stuff, actually. Because, you know, especially if you're going to do 45 minutes i'd you know i would write jokes about the olympics or the presidential election or whatever was going on so you had the joke i had the joke so i just typed up like 50 jokes for my act and sent them in and they were like yeah okay you start tomorrow or whatever right yeah and the weird thing is when I was a kid, you know, I grew up in Newton and I went to this Sunday school that was at this convent in Brookline. Yeah.

And I was in Conan's brother's class. You knew him? Yeah. You remember him. And Conan was in my brother's class. Uh-huh. So, and then my brother ended up going to Harvard with Conan.

So they're both in the same year. So I'm going to Ding Ho on Wednesdays in Cambridge. And my brother's at Harvard and I would go and have dinner with him and then I would go do the show at the Ding Ho and that was like my every Wednesday and was he friends with Conan no like they knew each other and right and Conan was writing for the Harvard Lampoon right and he would sometimes go oh remember that guy Conan and he would give me like the Harvard Lampoons and I'd read stuff that humor things that Conan had in this thing. So I kind of was aware of him. Yeah.

But was he that aware of you? Oh, no, no. He was, I mean, he knew who I was. Right. But he knew your brother. Yeah, and he knew my brothers, but he barely knew, you know, and I would have walked past him on the street.

Like I wouldn't have known what he looked like or anything like that. But I kind of, you know, when you know somebody growing up, but then you see their name on, but then you see their name on SNL or you see their name on Simpsons, it's kind of like they're in the major leagues. You kind of know who they are. And also, like, does it seem more possible for you? Or at that time, had you given up on your TV writing dream and you just saw yourself

as stuck in stand-up? Well, I did see, I would kind of, I would still write like a spec script for like a Cheers episode or something like that. Oh, you did that? I would try to do would kind of, I would still write like a spec script for like a Cheers episode or something like that. Oh, you did that? I would try to do that kind of thing. And did you send them out or did you have representation? No, I had nothing. And they went nowhere.

And, you know, it was, you know, and I'm sure they were bad. It's a hard, weird feeling that like, because I didn't really have those aspirations, you know, when I was doing standup. I just wanted to be a standup. Sure. conversations you know when i was doing stand-up i just wanted to be a stand-up sure but i i have to assume that you know after what like uh like six seven years in the business and you're doing all those stand-up gigs to have that moment where you're like i guess this is it right sure i you know i it's funny i i i sort of naively thought things would work out i i'm not when i look back now you know when i was you know i got married at 30 and my in-laws were totally cool with it or whatever.

You're just a stand-up. I'm just a stand-up. And now- What'd she do, your wife? She's a, does computer consulting. And so she's got a good job and she was working for Price Waterhouse at the time and she was making a good living. And I had my little meager income.

Going out and working in nightclubs. Absolutely. And just to think that it's like, really, I got married and I had this i was i had i don't know where i had the she must have had a vote of confidence yes yeah absolutely and you guys stay together and i think now it's like what were you thinking you know and what were your parents have you ever asked why are your parents okay with that well they they just want their kid to be happy i guess so yeah but did you ever ask her that well yeah she's like oh they like she's, yeah, my parents always thought you were great. And I thought if it had been the other way around, like if my sister brought a comic home and whatever was getting married, my parents would be like, what the fuck?

You know what I mean? Yeah, yeah, yeah. I don't think they'd be on board. Right. But you're a good guy. Solid. I guess that, you know, I don't know. I don't know what to tell you.

So you get the gig. You know, I don't know. I don't know what to tell you. So you get the gig. Now, this is the thing that always fascinated me is that I remember because I was doing the show by then a couple times a year. And I saw you. I was happy to see you. I'm always happy to see you over there.

And then, like, you lived with Todd Berry. I did, yeah. For what, in my mind, was a decade. It seemed like a decade. Well, you know, this is what happened. But you were never there. Right. You'd go to Todd's house. Like, yeah, Brian's in that room. Yeah. Well, you know, this is what happened. But it was like, but you were never there. Right. You'd go to Todd's house, like, yeah, Brian's in that room. Yeah.

Like, down this hallway. It's like, is he ever here? But, like, it was always sort of impressive to me, and I always wanted to ask you, like, did you not think it was going to work out? Because by then you had a kid, right? Well, yeah, what happened, here's the thing. Yeah.

The start of the show, and the show was very shaky. Right. And people don't remember how, you know, it's just seemed like it was going to be this temporary thing. And I get this job and I said to my wife, well, I'll go do this for 13. You own a house up there? Yeah. Oh.

So we had a house in, in, in Newton. Yeah. And in Auburndale, we had like a little starter home, you know? And it was like, well, I'll go do this for 13 weeks. Yeah. Put a little money aside and then you know maybe save a little bit of money or whatever kids at that time no uh-huh so and every day you'd be reading the paper about who's going to replace conan you know i mean literally you'd be reading the not the

new york post the daily news like well conan's going off of course because it's like who's going to replace him and it was like oh shit and one time where i'm in the office with agne our assistant our accountant comes in. She's like, okay, you guys have two computers, a TV. He's like, oh, they take an inventory. We must be going off the air. They had to call a meeting of the show and go, no, they take inventory once a year. We're not going off the air.

Like that's how shaky it was. And I only had 13-week contracts at a time. Every 13 weeks, you'd have to wait and get the thing in the mail. Like, okay, you've been picked up. Right. So you didn't know if you're going to be canned or whatever. And my wife had, my wife had this great job,

but she was making twice as much as me. Right. So people like, well, you should move to New York. It's like, well, not really.

Do you know what I mean? Like it seemed, so it's more like I should stay home and I don't know. So, but it went on too long going back and forth but they also what would you do you you'd come down on a monday morning i would come well in the beginning i'd come down on a monday morning yeah i'd take the delta shuttle and then i'd come back on a friday night and in those days you could just get on the plane at 6 25 and get on this

get there at 6 25 get on the 6 30 plane right but then I had a kid, they let me work from home like two days a week. Oh, really? One or two days a week, yeah. So like you could stay like Friday through Tuesday? Yeah, I would show up Tuesday morning

and then I would go home Thursday night. And so it was, you know, or, you know, depending. And also we got like 10 weeks off. Right. And then I was just home with my kid, you know.

You have two now? I have two, i have two yeah so it kind of went up but for a while i was living with todd which is kind of hilarious yeah i can't imagine that well he how did that happen um i think i think maybe through kozlowski i don't remember somebody said you know todd needs a roommate or something i remember his first roommate actually vaguely. They knew each other from Florida, I think. And then he had that room down that weird, that was not a great apartment.

No, no. But he had this little hallway and there's this room there. It's like a bunk bed in there or something. Yes. It was like, it was, it was like, it was like up on a, it was like this raised thing. You had to kind of crouch under it. Yeah. And like, like you couldn't, if you know, you had to lie flat, like you'd bump your head up. You couldn't sit up. You couldn't sit up under it. Yeah. And like, like you couldn't, if you know,

you had to lie flat, like you'd bump your head. You couldn't sit up. You couldn't sit up in it. Yeah. So, but I was there like three nights a week or four nights a week.

And he was, he was out till like 2 a.m. Yeah. Oh yeah. Yeah. So I'd come in, I'd do a set and then I'd,

but I'd only do like the early show, an early show. And then I'd be in, cause I had to, one thing I learned was if I got in at 1 a.m., got a shitty night's sleep, and I didn't get jokes on the next day, it's like, what am I doing? Because I'm doing a set in front of eight people and whatever. Right, that Boston Comedy Club?

Yeah, that kind of thing. Yeah. Exactly. So I was like, all right, let me be in by... Go to bed at 11, do whatever. So I didn't see him that much. But I didn't have anything. I just had

like this mattress on that the raised thing and how many years did you do that well i did that i guess i did that for a year or two that was it well yeah then i did then i roomed somebody else for a while another comic uh she was a it was a woman who did improv oh and i didn't see her either i mean she was out doing yeah but i remember Oh. And I didn't see her either. I mean, she was out doing it. But I remember with Todd's place, I had nothing. Yeah. And at night, I would go in the bathroom

and I would, that was the only place I had the light. So I'd put the toilet seat down and I would just sit on top and I had the light from, you know what I mean? And I would just sit there. And it's the kind of thing,

I still do that, like when my kids, we'd go to a hotel. Yeah. And my kids and my wife, they'd go to bed at nine o'clock. Well, I can't watch TV or whatever. I just go in a hotel. Yeah. And my kids and my wife, they'd go to bed at 9 o'clock. Yeah. Well, I can't watch TV or whatever.

I'd just go in the bathroom and put the toilet seat down and read. You know, I've done that like 100 times. So I would do that in Todd's room. So every once in a while, he'd come home. Yeah. And he'd knock on the door and I'd have to, I'm like, oh, sorry. Because he needed to use the bathroom and I'm in there reading. So finally, my wife came.

She's like, why don't you just get a lamp and a, she just got me lamp and a chair it's like here you can sit in your room that's so funny it's comics just like these basic things are like oh yeah i i'm so you can just go buy a lamp get something for myself like i'm kind of like oh fuck it i'm fine right because you came over here and you're like it's a nice house because some comics i don't know man they just live in these hovels it's true though yeah like i don't if it weren't for women in my, I'd be living out of milk crates on a futon. Oh, you know, all my clothes, everything. It's like, now with the clothes, I wouldn't have clothes if I didn't have a TV show. Like I just, the wardrobe is sort of like, you want these shirts? I'm like, yeah, I have four shirts. I'm glad you got my style. So nailed. I know it's, it's kind of crazy. It's true. These books I've been carting around forever. Well, that's, and that's the thing. That's what she gets mad at. It's like, you know,'s true. These books have been carting around forever.

Well, and that's the thing. That's what she gets mad at. It's like, you know, I have all these books. And it's like, you know, the Kindle, it's like $15 for a Kurt Vonnegut book that I can get for a buck at a used bookstore. Why would I? You know what I mean? Oh, really? So it's like I love having that kind of stuff. I've got books on the-

Yeah. I don't do the Kindle either, but I've done it on planes now because I travel a lot and I used to travel with two or three books I wouldn't even read but I'm like I'm going to get to this on the plane and every once in a while there's like a long layover good thing I brought these three books

but most of the time it's like I don't have time to get to all this no you're just traveling with books and they're heavy I know so you had no experience in doing what you got this job to do. Yes, not at all. And what was the learning curve, really? I mean, is it just sort of like, here are the sit and write jokes?

Do you know the guy? Well, you know what? I was fortunate in a couple of things, in the sense that it didn't take me long. I got his voice almost right away, only because we had similar sensibilities. He's from this big Irish Catholic family. I'm from this big Irish Catholic family.

And we did the map quest one time, and it was exactly He's from this big Irish Catholic family. I'm from this big Irish Catholic family. And we did the MapQuest one time, and it was exactly four miles from his house to my house. Uh-huh. But there was just in terms of, sometimes somebody would write a joke that's just too dirty. Right. And I'd be like, and I'd feel uncomfortable delivering it, you know?

And he'd be like, yeah, I can't do that. It's too graphic or whatever. Because you would have to tell him all the jokes? You were the head monologue guy, basically? Well, no, not at that time. We would just give him the jokes. And sometimes somebody would push for one that's like,

that I could tell he felt uncomfortable. And I felt, it's like, I would, do you know what I mean? So I didn't write jokes like that. I kind of wrote jokes that were in his wheelhouse for the most part. The only thing I had to do was, there would be like a wordplay joke that I would think is a clever joke. Yeah. And he hated that. And I had to do was there would be like a wordplay joke that I would think

is a clever joke yeah and he hated that and it was I had to learn like oh he doesn't like word he doesn't like that wordplay so I kind of and I got and I stopped doing that for my act just because I got so used to not doing that yeah but that was something that I liked at the time and thought okay well this isn't this is clever or whatever it's like no it's corny it's like oh okay noted yeah so yeah so i i was able to kind of write for him pretty quickly i used to love when i'd co-do the show because i'd be usually like the second guest sure but it'd be funny like all you monologue guys would hover around the monitor to see if your jokes oh yeah worked oh well that's just it there are times you're a tank and i remember one time you, the monologue just tanked at one night.

So the next day he comes to my office. He's like, how do you feel when you send me out there with that shit? And I said to him, I said, you know, in the movie Rear Window, you know, Jimmy Stewart's got the two broken legs. And he's looking out the window. And he thinks that Raymond Burr has killed his wife. Yeah. So he sends his girlfriend, Grace Kelly, into his apartment to look around, and Raymond Burr comes home. Yeah.

And he's watching, helpless. Yeah. And Raymond Burr starts manhandling her. And it's like, that's how I feel when the monologue is going. You're just helplessly watching him. Did he laugh? Oh, yeah, yeah. But you're just like, oh, no, he's going down.

And now, I mean, he's gotten where he's able to learn to deal with it. He can save himself. Yeah, but, you know, but in those days, he was... He looked so terrified

at the beginning. Oh, yeah, yeah. Can you imagine doing... You have never done stand-up before and it's on national television? Yeah. Like, my, you know,

if my open mics were on TV or whatever, it's like, that's who I was. Oh, yeah, no, I definitely felt for him. Oh, God, you know. And were you a big Carson fan? You were? I was, yeah. Yeah, he was great, right?

He was great. He was great. Yeah, it's so funny to see who learned from him and who didn't necessarily. Like, when you would go to the Museum of Broadcasting, back when you had to do that, you'd get like these four-hour blocks. Sure.

Where you'd have to sign up for something. They had to go find it somewhere. Yeah, yeah. And they'd assign you a little cubicle and you'd have to wait. I loved it. What'd you go watch? I would watch like the Jack Parr show.

I would watch like Woody Allen doing stand-up on TV. That's exactly what I watched. And the Jack Parr. There was some part about the Jack. Like there was some, like Jack Pryor had this reputation as the guy. Yeah, sure.

Who would just sort of shoot the shit. Was it the Tonight Show that he hosted or was it another show? The Jack Pryor Show, I think. Right, but I think it was the... It was the Tonight Show. I think so, yeah. I don't know what the...

But I remember going to watch Jack Pryor. I remember going to... I watched Woody Allen's NBC Variety Show. Oh, I didn't see that. I would have liked to see that. With Billy Graham on there. Parr. I remember going to, I watched Woody Allen's NBC variety show. Oh, I didn't see that. I would have liked to see that. With Billy Graham on there. Oh, I didn't know about that. I wouldn't have seen that.

Yeah, he had Billy Graham out. Oh my God. And oh, you watched the Richard Pryor show? Well, I watched Richard Pryor do standup on Jack Parr or something. And I would watch Woody Allen do standup on Jack Parr. You know, that was just to see them come out and do their sets as sort of unknown comics was fascinating. And I'd see Bob Newhart, guys like that doing...

Mostly stand-up then. Did you watch... I'm sorry, go ahead. No, no, no. I used to watch Jonathan Winters on Jack Parr. Oh, yeah, yeah. Unbelievable. It's too much, man. Yeah, unbelievable.

And even watching Jack Parr's monologues, there'd be some jokes where you're like, we'd do that joke. You know what I mean? Yeah, yeah. Like, we'd do that joke today. And it's like, you know, it wouldn't be Elizabeth Taylor and Richard Burton, but we'd do it about Brad Pitt and Angela Angelou or whoever. Right. You know what I mean? It's like with the same structure, we'd still do that joke.

I think the structure remains for better or for worse. Yeah. So, okay, so you're there and you finally, do you ever move the the structure remains for better for worse yeah so okay so you're there and you finally do you ever move the family i did yeah yeah we moved to new york we moved to west oh you did yeah yeah yeah and she kept it she got her job well she well this is kind of what happened i was going back and forth and then um well what you know we started getting nominated for emmys yeah so one year we get nominated for an Emmy and my wife's family lives out.

Like her sister and her brothers were living in Southern California. Right. And her parents are going to be visiting. She said, well, why don't I go out a few days early with the kids, see my family, and then you come out on the weekends

and we'll go to the Emmys. So we're going to go. So she makes all the arrangements and a week before my daughter gets a hernia. So she has to have a hernia surgery. And then the doctor's like, you know, I can only take them out on that Tuesday for whatever reason. I can't remember if he was, I didn't take her, my wife did. So I don't remember if it was at the hospital. He was either only at the hospital on Tuesdays or only in his office on Tuesdays. But anyway, he had to take it on Tuesday.

So my wife had to change the flight. So, you know, it turns out it was 9-11. Yeah. So they were booked on that flight 11, 9-11. But because of her hernia, they pushed it back a day. So we had to, you know, change our flight and whatever. So it was kind of, you know. Wow.

Yeah. So both my kids and my wife were booked on that 9-11 flight. Oh, my God. And I went to the airport that morning. I was flying out to New York. I was going to go take the Delta shuttle to fly to Conan. And I get there and they're like, oh, there's a plane crash. So there's a delay.

So I'm just got the USA Today and I'm at the Dunkin' Donuts and I'm writing my jokes, you know, and then the other one crashes and it was like, oh shit. And then they closed the airport and send us home. But I, I didn't realize what was going on,

you know, and I'm in the cab and the guy is saying that the, the towers come down and I'm think, well, they don't mean the building. There must be a tower on top of the bill. Like it's like a radio tower on top of the bill. You. And I'm thinking, well, they don't mean the building. There must be a tower on top of the building. Like a radio tower on top of the building. You know what I mean?

And it's like, talk about denial. It's like, you know, and I get home, and my wife, she's like, that was our flight. That was, you know, like when I left that morning, she's like, oh, it's too bad we all couldn't go to the airport together as planned, you know? Oh, my God. I know, I know.

So it was really crazy. And that's what drove you to move well what happened was then you're one of the few people that moved to New York that's true yeah but it became hard to I couldn't just get to the airport and get on the flight you know it became like a giant hassle yeah and then she was unhappy with her job so it was like once she quit her job it's like well what are we doing yeah so she moved to New York, and then we lived in Westchester for several years. Right. And my kids loved it there, actually. And then we moved out when Conan moved out.

So you're like Conan's, basically, you've probably been there the longest. One guy was from the very beginning. Who? This guy named Michael Gordon. He's not a monologue guy, though. Right. And he and I share an office very beginning. Who? This guy named Michael Gordon. He's not a monologue guy, though. Right. And he and I share an office. Veterans.

Yeah. But you've been through Dino. Oh, yeah. And all the guys that came through. Oh, yeah. And it's unbelievable. Who are some of the people? Like, Odenkirk was there?

Bob Odenkirk was there. Although, he was mostly living in L.A. Yeah. With send-in stuff. But Dino was in town, right? Dino was in town. Oh, yeah. It mustino was in town right dino was in town oh yeah it must have been crazy times dino is crazy and he's so he's so funny but he was there at the beginning with you right there at the beginning yeah absolutely uh louis louis and you know

smigel and and those you know it was but the sketch guys would be there till two in the morning or whatever you know yeah um it's hard to make that ridiculous shit. Perfect. Yeah. Yeah. And especially we didn't know what we were doing, you know what I mean? We were kind of finding out.

So there was there, there's, is there always sort of like a, a, not a wall, but like, you know, the monologue guys are the monologue guys and the sketch guys.

Yeah. There always has kind of been that. And you guys just sit there hammering out jokes and occasionally poke around and go like, can you tag this? Yeah. Here's a setup. Yeah.

Do you do that? Oh yeah, absolutely. And absolutely and it's also there's and it's like does this work or it's like i'd say it like this or that kind of thing you know but like we would do they started having us go do shows four days a week and give us one day to which was a break and then we would work on year 2000s or other stuff or stuff that you could feed jokes into that were established yes pieces yes absolutely okay yeah i wrote a a real joke recently about getting i got a sonogram of my heart you know to see yeah i got a son and i'm and i'm proud to say it's a girl great i love it love it so is your health okay yeah good i, good. My cholesterol is a little high, but it's genetic, I think. Well, I've been following with the show, so I know what's going on.

Well, thank you. I appreciate your concern. So let's talk about the transition and the panic of, so you get the Tonight Show, and you're going to be writing for what Carson used to host. Yeah. That must have been amazing. Well, it was. It was weird in that there was this, know it's 2004 and they call a meeting

in the show and conan said i just got off the phone with nbc whatever i'm gonna be hosting this night i'm gonna take over the tonight show in 2009 so here it is this five year and it's a little bit like someone saying five years from now on may 31st i'm gonna come to your house and punch you in the face you know and you know? And you're like, okay. I'll put it in the calendar. We got this thing that's going to, you know what I mean? And you're kind of working towards that. Yeah.

You know? So it was just, it was crazy how long we were waiting for this thing, you know? You must have put it in the back of your brain, though. I mean. Oh, yeah, yeah. But, you know, and my son really wanted to stay in New York. How old is he now? He just turned 20 20 he's a sophomore

in college wow yeah and he you know in our little town we had a town of 5,000 people he knew all the kids it was yeah you know how old was he then so he was he was 13 oh so it's tough time yeah it's tough time to move you know uh and where my daughter went to school with a lot of mean girls she was kind of like okay let's get ready let's go yeah so and it was just like it was just tough where it was a tough transition for him and then she embraced la right away what part of town you live in uh studio city oh okay that's good and that's where you started right well you got a house right out of the gate yeah we did and we thought you know we thought we're going to be working on tonight show for 20 years or whatever you know and it's like it's like

people like the traffic is bad make sure you get someplace close to work and it's all that kind of stuff so um you know little did we know in seven months it would be out of there you know what was it like when he started writing on the on the tonight show and everybody was excited it what how many weeks was it before you're like oh we're fucked well i have to say that it was tremendous pressure and and even though we you know when i first started conan he did like four jokes in the monologue yeah and you'd get two jokes on and be like yeah doing all right you know and then he slowly got a little started ramping it up a little bit but he never never did more than, say, seven or eight.

At the old show. At the old show. So with the new show, The Tonight Show has this long tradition of having a long monologue. So he'd want to do like 13 to 15 jokes. Right. So you went in all day and you never looked up and you just wrote, you know, you're writing 50 or 60 jokes a day. Yeah. And I had to knock my stomach every day.

Like back in the old days. Yeah, yeah. I really went home. And I, you know, in New York, if we had a good day, he's picked a bunch of jokes. I'd give my dad a call, see how he's doing or whatever. He was in Florida or whatever. Where this, you know, plus it's the East Coast.

Like I'd get home, I'd write all day. There's no time to call him any day. We never had a good day. Right. You know, we never had an easy day we could relax. And I'd get home at 7.38. It's like, well's no time to call him any day we never had a good day you know we never had an easy day we could relax and I'd get home at 7.38

it's like well I can't call him you know he's been in bed for two hours you know but it was just I was like a dishrag

at the end of every day it was so much pressure and so much stress so even though we took a hit financially and we're not as you know

as relevant to a show now or whatever because we're not on the network. But personally, it's a lot less stress. It's actually a lot more enjoyable. And I think the show is much more fun than it's actually fun. Oh, definitely.

But all the way through, the stress was happening. And then when you actually got taken off the air, it must have been devastating for everybody. Oh, yeah, yeah. Yeah, absolutely. I mean, we were all crushed. And, you know, I remember about two weeks after we got kicked out. Yeah.

Or he left, whatever. I mean, he basically said he didn't want to do the 1205 show. And so he didn't really, he didn't get fired. He told you first? Did he let you guys know? Yeah, yeah. The decisions he was making? He did.

And he decided, he's like, you know what? I don't want to be treated like this. So I'm out of here, which I understand. So, but it was suddenly, it's like, you know, I moved my family across the country. My wife wasn't working. We bought a house. We put our kids in these two private schools

and now we're fucked you know and i remember there's about two weeks later there was an earthquake and it was like three in the morning oh no and i'm wide awake like i probably started at four in the morning but three in the morning i'm wide awake yeah so i'm sitting there just lying in bed like what am i gonna do right and then this earthquake happens and the next day people like oh that earthquake woke me up whatever and i felt like oh no i'm wide awake waiting for it you know and i'm living yeah and i do remember when the thing when it first got the news that this hat was we were getting pushed off the air whatever i think i was just in shock for like a week i people were crying and people and i had no reaction whatsoever and then

my wife's birthday is a week later we go out to dinner with this other couple and they're talking and they start talking about it and all of a sudden it just hit me yeah and i don't think i said a word for an hour and a half like we're just having dinner and all of a sudden i'm like oh fuck you know what i mean yeah and they're all talking whatever and I'm just like in my own world, like, it's over. It's over. You know? But it was reported that, you know, Conan covered everybody for a little while. Well, he did, although he didn't, the writers weren't part of that because we kind of had our own deals. Right. So I still had, I was still getting paid for NBC for, you know, for a few weeks after that.

you know, for a few weeks after that. Right. And I had taken this writing class in the fall, and I would write, I wrote what I thought was a short story. Right. And then teachers were like, well, that's not a short story. That's the first chapter of a novel. And I was like, oh, it is? So the next week I'd bring in the next chapter,

but I didn't know where it was going. Right. So when this happened, I was like, you know what? I'm going to work on my book. I needed to do something. And we have the book. We have the book, yeah. The book has happened. Yeah, the book book. I needed to do something. And we have the book. We have the book. Yeah.

The book has happened. Yeah. The book happened. The Astounding Misadventures of Rory Collins started at the bottom. You were at the bottom. I was at the bottom. Yeah. So that actually helped me through that period.

This book. Yeah. It really, because I didn't want to sit and be unshaven and sit in sweatpants all day. Do you know what I mean? Oh, yeah. So I got up. Regressed to comic status. Yeah.

So I got up. I showered every day. I shaved shaved and then i would go right for like three or four hours and just having i think i need structure and having that something to do carried me through that you know and i imagine that that writing something like this book is uh it was new to you totally yeah absolutely and i love to read and i love but it was so liberating to actually have characters and have a story and say fuck yeah and you know do stuff you know that that exciting sense of discovery yes of writing a book like to sort of like see like i do have an imagination yeah yeah narrative one yeah so that was really what's it about exactly it's about this young guy who has he sort of has this crazy mother he's got this sort of insane childhood and he's very passive and he's in college he loses his virginity with

this woman this pretty woman and then her roommate is in the bathroom crying because it's like oh everyone always wants to sleep with her and not me because she's not so he ends up having sex with the other one too whatever which actually

this happened to a friend of mine oh it did yeah so that story always stuck in my head yeah and then suddenly that woman started

bringing her her lowly friends to him to lose their virginity and he was like this passive guy who was just sort of and all of a sudden he's having sex with like the dregs of the,

you know? Yeah. And, and then it just leads like he, he's, his passiveness sort of gets him in trouble and, and right. Yeah.

And that's sort of the story, I guess. And does it end well? Uh, I don't want to give away the ending, but it's actually much, it's pretty dark. Yeah.

Um, finally, you know, I, the ending, but it's actually much, it's pretty dark. Yeah. Finally. The real Kylie comes out. You go in a room by yourself and it's all like, it's super dark and you come out like, wow, what did I think? I had no idea that was exciting. Yeah. That was. Did you finish the book in the interim between the shows?

I did. Yeah. Yeah. I mean, I had to rewrite it when i was that sort of interesting that this was you know your your your way of managing yeah oh absolutely you didn't go out and look for other tv jobs no no and i did i did do some stand-up but i didn't uh yeah i didn't because you know i how how quickly after the um the mb the NBC show going away was Conan starting to talk about the negotiations for a show with the writers? That's a good question.

You know, we got off in January, and then I think we came back in September. So it must have been at least pretty quickly after that you were informed that maybe there was going to be something. Yeah. I mean, he had told me that he would put me on, you know, he would hire me on his new thing. Right. But we didn't know if he was getting a new thing. Right.

So there was about a six month period of like, hmm. And he wrote the book. Yeah. It's amazing how things that you might not have ever gotten to. That's true. Happen in the darkest times. That's why this podcast happened. Really? i had nothing going on i just been divorced twice i was broke and you know this was born out of that like i don't know what i'm gonna do was the podcast

your idea yeah we you know i just we'd lost a job uh at air america again we're doing a streaming video show and me and my producer were like let's try try this thing. Let's do it. Let's just commit to a couple days. That's great. Yeah, but it was definitely the darkest point of my life. Oh, yeah.

Horrible. I had no idea what my future was because I didn't prepare. I'm not a writer, TV writer. Sure. Well,

it's true. But it's funny though when you read biographies of famous people, you see people and you think, wait, that famous artist

was really starving and he was – Right. The starving artist thing is real. Yeah. It may not be literally not being able to eat. Right. But certainly not with many prospects. Yeah.

And no real choices in your mind. Yeah, absolutely. So the new show starts and it must have been very exciting to have the freedom and have the support of the network. Oh, yeah, yeah. And plus, you know, it's weird. We can actually swear sometimes. It's just looser.

Like, we're also, we're kind of just doing the show for our fans as opposed to trying to win over middle America or older people or whatever all these things we're trying to do on The Tonight Show, you know? And the audience is holding pretty well? You know, he has a real loyal following. And also, we have a lot of people watching, you know, on their phones or on the computer the next day, that kind of stuff, you know? And are you going to work today? I am, yeah.

Yeah. What time you got to be there? Well, I told him I'll be a little late because I'm doing Marin. We don't have a show today, so that's... Right. And he went to Swide? Yeah.

Well, Sweeney's taking his kid to college, so it's kind of kind of worked out perfectly oh sweeney's been there a long time too now yeah because i've known like i knew well i didn't know smigel but you know john groff had his first writing job for me oh oh that's on comedy central yeah and was you and cinderelli were doing it right that was his first writing and cinderelli was on the show with yeah he was my uh my sidekick yeah yeah it's sort of funny but groff went on to be the head writer of Conan. Yeah, now he's- But now he's busy, right? Now he's running that Black-ish.

Yeah, I had breakfast with him, like brunch with him, like a couple months ago, but he is super busy, yeah. And the book is out, right? Yeah. The Astounding Misadventures of Rory Collins. Brian Kiley, great talking to you. Thanks, buddy. That was great. It was great seeing brian great talking to him a lot of stuff in there you go to wtfpod.com for all your merch you want to buy some posters

or things wtf related for christmas presents go there and do it get on the mailing list i'll write you an email every week i'm so tired i hope it didn't read i hope you didn't hear the tiredness i have to go back to work now and and work on my show uh i'm not gonna play guitar today because i have to run but uh but i will do this boomer lives It's a night for the whole family. Be a part of Kids Night when the Toronto Rock take on the Colorado Mammoth at a special 5 p.m. start time on Saturday, March 9th at First Ontario Centre in Hamilton. The first 5,000 fans in attendance will get a Dan Dawson bobblehead courtesy of Backley Construction. Punch your ticket to Kids Night on Saturday, March 9th at 5 p.m. in Rock City at torontorock.com. Discover the timeless elegance of Cozy, where furniture meets innovation.

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