Inside Conan: An Important Hollywood Podcast - Writer Brian Reich Revisits Masturbating Bear and Pimpbot 5000

Episode Date: November 5, 2021

Legendary Late Night writer Brian Reich joins writers Mike Sweeney and Jessie Gaskell to discuss the origins of Masturbating Bear, the literature that inspired Pimpbot 5000, the Late Night office game that involved getting punched in the head, and how he pulled off what is possibly the craziest prank in Conan history.Got a question for Inside Conan? Call our voicemail: [phone] and e-mail us at [e-mail] .

Hi, Inside Conan listeners. It's Mike and Jesse, and we wanted to address something before we kick off this episode. There was an ad that went out on Inside Conan last week in error. I don't want to go too far into it, but for our listeners who heard it, I want you to know that it is not reflective of us or Team Coco. A third party facilitates our ads, and there was a mistake on their end, so it ended up being delivered to a small number of our listeners. If you heard the ad, we're sorry if it caused any offense. Thanks for listening, and we hope you enjoy our interview with Brian Rich. And now, it's time for Inside Conan, an important Hollywood podcast.

We are your hosts. I'm Jesse Gaskell. I'm Mike Sweeney and we're both writers. We've been longtime writers with Conan O'Brien and all his various shows. We write all of his podcasts. That's right. That's right, but not his ad copy. No, never. That's where he gets to shine. Yeah. What have you been up to, Sweeney? I know that you are busy helping prepare for Conan's first live podcast recording at the Wiltern Theater. Okay, well, busier.

But the goal, I think the goal of their live podcast is to kind of, you know, stay true to their successful podcast formula. So it's really just transplanting Conan O'Brien as a friend. Conan making fun of Sona. Exactly. And Sona giving it back to him.

Now with a theater echo added in. That's the big change. But that's taping tonight, actually. That'll be very exciting. At the Wiltern Theater, the historic Wiltern Theater. Yeah, that's a huge venue. That's really cool. And I think it's going to be extra exciting because I know for Conan, he hasn't really been in front of a live audience since June.

Oh my God. He is going to be milking it. When Conan wrapped. Yes. It might be an eight-hour podcast. It's just going to be in one long-standing ovation. The crew will be like, we've got to close. It's 2 a.m.

He's still going. He's making up fan questions that don't exist and answering them out of control uh and you're going it'll be fun to see everyone i'm i'm gonna be there yeah good great i get to meet one of our producers in person for the first time that's That's right. She's flying in. See if she has a bottom half. That's true. I'm sorry, Joanna. What else? I heard you went to a concert. Oh, I went to, first time in my life, well, it's Dead & Company. Oh, yes, The Grateful Dead, but without Jerry Garcia, I'm assuming. My adult sons have just become huge Grateful Dead fans.

I think because I... It skips a generation, I think. Yes. Well, I played, I think, a wide variety of music for them growing up, but never the Grateful Dead. And this is... So that's a tip to parents. And they were like, we already have the tie-dye shirts. We might as well but if there's music you don't want your kids to become obsessed with as adults make sure you play

it for them as when they're younger so it's it's something they they can't discover later like why did you keep this from us right but i so i went and how How fun. It was. Right before we went, they're like, it's a four-hour concert. Yeah. So I lost, yeah, it took me- So here's three edibles. Right. One thing I learned is they have something called Shakedown Street, which is where they tailgate, all the fans tailgate, and all the vendors tailgate. And that, before the show, and that was great.

Oh, well, see, i would have wanted to go to just that part i think that's i was quite happy with that and yeah gone home after that and i learned that nitrous oxide is a big nitrous oxide in balloons oh is that the drug of choice yes i think it's called the hippie crack. The LA police could have gotten all their drug arrests taken care of in this one parking lot. What does that do besides make your voice squeaky? Oh, no, that's Healy. Okay, that's Healy. I don't know, but they should have had dentists, like roving dentists around there.

Oh, yeah, right. But yeah, did you ever have laughing gas like when you're a kid from the oh getting my wisdom teeth out yeah it's amazing yeah i i never i never loved it oh you didn't you didn't have a good time no maybe it's because it involved wisdom teeth and pain so i always associate it with maybe I should have done it before the show. That doesn't speak well, though, of the concert itself, if you have to have dental grade.

I agree. I agree. Anesthesia to enjoy it. And then, you know, there was the morphine tent, which I also thought didn't speak well to the band. A lot of ventilators. Yeah.

How was your week? Anything exciting? Well, I kind of got tricked into handing out candy for some friends on Halloween. Oh, I was going to say, I hope it was at least on Halloween. Oh, yeah. Okay. What do you mean tricked? Yeah, my friend Pennywise the Clown asked me to hand out candy.

No, they live on one of those crazy. All of a sudden, I'm in a storm drain. Yeah. Halloween streets. And they were like, come over. We're having a party. You know, we're going to order pizza. It's going to be a grown-up party.

Sounds good. And then I got there and somebody shoved a bowl of candy in my hands. What? And I was stuck handing it. It was like a steady stream for four hours of children coming to the door. And I couldn't even get, like, there wasn't even a chance to take a break to tell someone else to come relieve me. Wait, you're, wait, so everyone else was having a party? Oh, yeah.

Everyone else was hanging out. I guess I could have just not. Yes. I would have just gone home. Not answered could've just not Yes I would've just got home Not answered the door Yeah I would've just slept with Just leave the candy On the doorstep

With a sign Were the adults In costume Cause that would really Fucking piss me off On top of everything else There were Yeah there were some costumes

I know I mean sure That's great fun And it So I had to be the The The grunt Oh no That's great fun. And so I had to be the grunt. Oh, no.

That's. But it was fun. I mean, I liked seeing. These are ex-friends. Trying to guess what costumes were. Yes, exactly. Okay, good. I'm glad you'll never see these horrible people again.

What were the big costumes you saw? I mean, lots of Squid Game. Sure. A lot of Squid Game, which I think is weird. I don't see that. How are children watching Squid Game? Sure. A lot of Squid Game, which I think is weird. I don't see that. How are children watching Squid Game? Well, are they? Yeah.

They were young children dressed in Squid Game jumpsuits? Yes. Did you ask any of them? Like, what was your favorite episode? I'm assuming they didn't. Well, I didn't want any spoilers. I'm not done watching it. Right, right, right.

Yeah. And then there were probably a lot of others that I didn't get right. I wish you had that red light, green light doll for them at the front door run children run yeah that would have uh i think solved my problem yes it would have okay speaking of treats how was that that is a wonderful thing we have a treat for you guys this week we do talked to the legendary late night writer brian rich brian rich is uh one of my favorite writers of all time just when he was on the show uh in the late 90s incredibly creative and um the proof's in the pudding.

He came up with some of people's favorite characters from late night, including the masturbating bear and Pimp Bod 5000. And one of my favorite lesser-known characters, Five Hooks the Pirate. Good luck digging up video of Five Hooks. You've scrubbed it all. Yeah, that's right. And so we were both very excited to chat with Brian and catch up with him. Yeah, and he gave us a really good, he painted a vivid picture of the chaos of early late night writer's room.

Yeah. It was, they were long days, very late nights, and 12 people trapped in a small room. lots of farting yeah well yes i didn't want to say that i wasn't there but i think that's a safe bet yes i have strong memories so here's brian ridge if you're a fan of conan and especially's late night with Conan O'Brien years, there were so many great sketches and characters that came up and were created in the mid to late nineties. These characters still come up all the time, Masturbating Bear, Pimp Bot, and a lot of really great memorable sketches. And when people ask me about them, I always mention our next guest who created so many of these memorable moments, Mr. Brian Rich. Brian, welcome to the show. Welcome, Brian.

Thank you. Thank you. Thank you for having me. Oh, my God. Yeah, it's long overdue. Yeah, it's funny. Actually, I think you kind of went out to me once to maybe see if I could do this show before. And this was when you were in New York. Yes. And I think that it's funny because I think I said I can't because I was working with Smigel. And then Smigel came and did it.

Yeah. You know, we were doing some like test like pilot thing for something that we ended up doing this year. Right. But I was like, I don't think I can. I really should go to this thing. Yeah. And then i get there and it's like where's robert oh he's gonna be in late he's doing this conan podcast and i was like okay great yeah well you created an opening when you said no yeah i know that's great he was getting calls from someone on your team i think during our podcast. Where are you?

Yeah, that's when I learned not to ever be a team player. Well, we're glad that we got you in between Smigled projects. Yes. We get so many questions about the characters that you've created. They're still some of people's all-time favorites. That's great. That's great to hear. Well, we want to go back to kind of to the beginning of your time on the show, because you, you came over from David Letterman, right? That was that was that your first writing job out of college? studio as you know late night with conan o'brien later was to be in so um yeah i worked for

letterman at the very end of his run at nbc there uh-huh and then conan was my next job after that what was it like starting at letterman right out of college that had to be were you intimidated or i was yeah i mean i i was really just excited to get the job. I think I got it about a year after I actually graduated. Okay. What took so long? Yeah, I don't know. I'm a bit of a slacker. Wait, so you were 23?

Yeah. So I was like, can I still write for young people anymore? Is anyone going to get my references? Yeah, I don't know. I mean, it was just really exciting. I mean, I remember when I heard I was getting hired and I was living at home with my parents in New Jersey. And I think that was like the biggest thrill of all. It's like, oh, thank God.

I get to move out. Yes, I can have enough money to get out of here and leave this behind forever. Once I explain to them who David Letterman is. Yeah, so moving back there after college was just a big mistake. But it did motivate me to... Right. That's a great motivator. Yeah, get a good application together.

Well, you were in the Harvard Lampoon, right? Right. That's where you probably knew all these people who had... application together. Well, you were on, you were in the Harvard Lampoon, right? So that, that's where you probably knew all these people who had. And you're like, everyone who graduates works in television. Yeah. Well, not, yeah, but yeah, we knew about, oh, you know, we'd hear about like this and that person who had gone on to write for shows we were into, you know. Right. And did you, had you heard of Conan at that point yeah yeah yeah conan amongst them uh conan was still you know he graduated way before me but he was still you know he was talked about because he was two-time president there of the the lampoon of the lampoon like overachiever always showing off usually you know it's always a senior is president pretty much uh so it was

kind of a unusual thing that he got elected in his junior year and senior year oh maybe that happened once before i don't know but but uh but now we know so much about election cheating and vote counting yes that's right i think we need to revisit his double presidency. It seems, yeah, it seems unlikely that that could have actually happened twice. So you did, so you had some awareness of Conan and so when you were at Letterman and you heard that Conan was taking over late night, was that a, were you surprised? Yeah, I think, I think, well, I mean, of course it was a little after Letterman that Conan got the job. Right. Wasn't Letterman off? Yeah, I think, well, I mean, of course, it was a little after Letterman that Conan got the job. Right.

Wasn't Letterman off? Yeah, he was definitely off NBC before they made the Conan announcement. In between, okay. Yeah, you know, I wasn't really ready to jump back into writing right then, but I remember thinking in the back of my mind, hmm, this will be something to watch, you know,

and see maybe this is a place I'll want to work. I guess I remember watching the early shows, you know, and thinking, yeah, you know, maybe, you know, maybe down the line this will be for me. Maybe if they find their footing. Right, right, right. Yeah, I guess we were all kind of excited. I guess we were like, yeah, finally, you know,

funny writers are going to step to the floor, you know. Like, why are all these, you know, meat puppets saying our jokes getting, you know, like, this is going to usher in a new age of the writer-scholar celebrity. Revenge of the nerds. Yeah. So that had to be a little weird. Your next job after Letterman was in the same studio or it was probably very comforting your did you act like guys i know my way around i knew where the commissary was you know what i mean what was i mean what were some of your immediate impressions of the the conan writing staff and just how how was it different from being at letterman it was kind of

wilder like when i was there we had a lot of late nights there because we'd eat dinner we do the show yeah then we'd eat dinner in this ugly awful conference room where if you didn't like the food it got like thrown up in the ceiling where tiles were missing and just to see what would happen to it after a couple months and uh and then we go back in to the to the head writer's room and work on whatever we had to crank out bits for you know the next day or the next few days and i i remember a game we started playing that i've tried to explain to people i think i know it's coming but i'm not sure but go ahead did you invent this game was it called baghead yeah yes baghead can you explain wait till everyone hears the rules uh let's see if i can remember exactly but yeah it just

gets so loopy and bored right that you just need something to stimulate you we were all very punch drunk yeah it'd be like 10 30 at night and i'm also someone who yeah hates just sitting still for hours like i just feel my body corroding right like you know i'm always like in writer's room for their too long getting up and pacing around and right but anyway baghead is uh it's a very it's a giddy game you you put a bag a paper bag i guess it was usually like the bag we had gotten our dinner in or something. Right. You put a bag over your head.

And then you would have to go around the circle of each person in the room, in the head writer's room. Like we'd be arranged kind of in a circle. Right. You'd go up to each person. You'd lower your head. And then that person would get a free snack of your head. Oh, my God. You didn't know exactly, you know, when it was coming. So you're kind of like, you know, you're kind of waiting. It's just kind of funny. You'd let the

person sit there for quite a while. And it wasn't like, well, you weren't like, you weren't like slamming the person that hard. It was just hard enough to be like kind of funny. When you brought this up, I assumed it was going to be some sort of way of generating ideas, like an improvisation game. But it literally was just, we're going to punch each other with the bag on. It took away ideas by causing concussions.

Brain damage. No, I explained that game to people. And I'm like, oh my God, it was so hilarious. You put a bag in your head and then go around and people punched you in the head. That's it. That reminds me when I was actually, it just reminded me of Letterman. There was a game

called Tub of Tea. You'd sit in a tub of tea and people would punch you. No, there was no tea or tub. It was also just punching you in the head with a bag. I think I see where you got this idea. Yeah, when we would order Chinese, they'd bring our tea. It'd be in these big plastic containers, and it'd be piping hot.

And it would always be, can you, you know, someone would try to drink the piping hot tub of tea, you know, and break the record for time. And you'd be trying to just down it. But it's scalding you so much. And everyone, of course, would be chanting like tub of tea, tub of tea. So you had to do it. You had to do it. But yeah, I don't know.

I think Baghead probably loosened things up pretty much. I remember, though, it being outrageous that at one point ellie would not don the bag ellie barancic oh right she's the writer's assistant writer's court yeah at that time and oh she refused to do it and we were all if you don't want to participate right but she had hit the bag head oh gotcha if you hit the bag you must also put your head in the bag, I think, is the fair rule. I mean, that's fair. And those are the rules that come on the box when you get the game. It's weird that the bag is boxed.

And I remember the head writer, he'd be like, you guys are hitting me harder. He was getting mad. And we're like, well, yeah, you're the one keeping us here so i'm sure that game still goes on today doesn't it or sure of course i can't imagine it dying out no something like that would never know as long as there are paper bags to be had it was terrifying um brian do you remember was not to put you on the spot, but the origins of Masturbating Bear? Because we obviously get a lot of inquiries about MB, and we just would love to get a real soup to nuts of Masturbating Bear and where that came from. Yeah, it's funny, Kirstie. If you Google my name and Brian Rich and Masturbating, Masturbating Bear is still one of the top three hits that will come up. That's great for him.

Yeah. And Mike, I think you actually, I remember you corrected me after a panel like years ago because I had forgotten the actual origin. I thought it was a new characters thing, which is the sketch we started doing afterwards, like just introducing it. Right. But what it actually was, was pleasing the affiliates. I also love that you already did a panel about masturbating parrots. Right. We need to get people to talk about this.

And then we broke off into separate discussion groups. Yes. Yes. Pleasing the affiliates. So, yes yes uh pleasing the affiliates so yes pleasing the affiliates so i just like the premise that the masturbating bear was a pre-existing character the idea was right we're from now on we're going to have the masturbating bear bound up right right so that he can't masturbate anymore i think it was like an affiliate, like Conan would read letters. Like I think it was like an affiliate. Or something like that, like somewhere that they'd be conservative.

And they were complaining about the masturbating bear, which didn't exist, you know, in reality as a character. Right, in reality. And so we are agreeing now to the masturbating bear would be shackled. And we had, you know, know the trainers which you and i actually played right like uh on we had cattle prods and everything we're going to make sure that the masturbating bear would no longer uh be allowed to masturbate when he appeared on the show yes what the masturbating bear in any conception was supposed to have been doing other than masturbating and all these other

appearances you know is left unsaid it still hasn't been addressed yeah so of course he you know he breaks free and he starts masturbating and right and then it yeah went from there i just had to think of new permutations i remember there was one where he was being totally good and not masturbating and then conan walks over to congratulate him, I think. And his hand passes through him and he realizes it's actually a hologram. And then we cut to the masturbating bear operating like a hologram machine. And he's been masturbating wildly the whole time. I forgot that.

It was just one beat in this desk piece, you know, a piece that's like five minutes long. Yeah. The crowd went so nuts for it that right away, it's just like, uh, I mean.

A blessing and a curse. Yeah. That's your bit now and you own it. Right. And it's, it's a double-edged sword. Cause you know, the, all of a sudden it's like,

we need more masturbating bear. And yeah, we need him in more and more precarious scenarios. Right. But after three weeks, it's like, we need more Masturbating Bear. Yeah. We need him in more and more precarious scenarios. Right. But after three weeks, you're probably like, oh, God, please, no more. You know, this isn't a rich, multi-dimensional character. Right. Yeah.

After I left the show, though, I don't think I ever watched Masturbating Bear. Well, I've seen a few, but I just didn't want to know. It's too painful. Yeah. After I left the show, though, I don't think I ever watched Masturbating. Well, I've seen a few, but I just didn't. I don't want to know. It's too painful. Yeah. They've cheapened it. It's not all about the masturbating. It's about the inherent tension between what the bear wants and what the show wants. There was one really great one. I don't know if you ever saw it. We were in Chicago for a week. Yeah. there was one really great one. I don't know if you ever saw it. We were in Chicago for a week.

Yeah. And so Conan's on stage at the Chicago theater. This is like 2006, I think. So it is after you had left the show. And, but he's like, well, you know,

people are like, where's the master being buried? You got to have them in Chicago, but I promise you, you know, it's a vile character. There's no way we would bring that character here to Chicago. And then you just cut to a pre-tape, and it was an airplane, a biplane,

and the masturbating bear skydives out of the plane over, like there was a cameraman skydiver as well who shot the whole thing. Before CGI. Oh, yeah. there was a cameraman skydiver as well who shot the whole thing. So you see, Oh yeah. You saw this amazing view of Lake Michigan and down, you know, the Sears tower and, and it was all to mission impossible music.

And we actually got a skydiver to put on the masturbating bear costume and jump. And it, there's one of those things when it was edited overnight and you know i think michael coleman and andrew and michael gordon and andrew weinberg edited it and like all the writers gathered around and just watched it like 20 times in a row on the on a computer because it just you couldn't believe it i'm surprised that the the bear suit didn't disintegrate from the, the air pressure against it. Skydiving. This is the bear just flying away,

you know? Well, they knew, they knew the first time you created it. This has to be, it's gotta be able to withstand air pressure. Yeah. Let's,

let's put in the extra money now. How did you cast who was actually going to play the masturbating bear? Because you didn't take that glory role for yourself yeah um i don't know i i you know if i knew that it would you know have such repercussions and go on i right longevity yeah i'm sure i would have tried to get in the bear suit you know that's just uh you tire on that stuff you could be doing appearances still i don't remember i think it was probably just a matter of on that stuff. Yeah, you could be doing appearances still. I don't remember. I think it was probably just a matter of Michael Gordon saying, you know, yeah, I'm not busy. Because when you're in something like that, you know, it's going to take a lot of the day out to go to rehearsals and all that stuff.

So if you're too busy with something. Right. But he also played a lot of mute characters on the show. Like he played like a giant ant and he did play a skunk and he he so he did all these kind of mimey giant costume like he played the stanley cup where he had a giant stanley cup on his body and you just saw his legs so it probably was like does this bear talk no okay it's it's a it's gonna be gordon yeah i he was this thing diz i think before right it might have been before i even started i don't know if they

stopped doing it by then but it's very early character of his diz was a character he would come out i think he had like um he almost had like a where's waldo kind of shirt on and would come out and just spin around to music and a sign that said go dis go until until he got dizzy and fell down right and he would interrupt the like i think i think his favorite time appearance was during a bob an interview with the real bob dole go dis go and he just comes up and he literally got so dizzy i think he half fell into bob dole on the couch that that was a sketch called not pleasing our affiliates right that's probably what led to the creation that bit do they they must still do that i remember now like after the show sometimes, Conan would have to stay out there for, like, another hour

and just film these little messages, you know, for the affiliates. Like, hey, TLU. Oh, yeah, yeah, yeah. Keep it going, Sam. You know, whatever. Like, hey, Santa Cruz. Yeah, people tend to go, wow, he really knows what's going on in our town. You know, like.

Right, right. We're cruising to great ratings, thanks to you. Well, and another one of your famous sketches was Pimp Bot. Yes. Can you really quickly explain the premise of Pimp Bot to anyone who might be unfamiliar? Pimp Bot was a, well, it's... It's in the name, much like Baghead. Right.

If you're an entomologist you could probably he was a uh robot pimp yeah he combined the sensibilities of a 70s street pimp with that of sort of a 50s sci-fi robot and he would come out and move mechanically and he would uh talk about you know his hose and he would threaten conan with a switchblade he would threaten to make conan one of his prostitutes if conan pushed him to r that's right oh and conan always be like i'm hosting the show i don't have time to prostitute myself in the way in the way you envision but But otherwise. Yeah. Right. Otherwise, full speed ahead. Which also, it seems like started as a one-off character and then was so popular that he got his own spinoff series. Because didn't it start...

I think he was from a new character. Yes. That one, if I'm not wrong, Pinpop 5000. Mm-hmm. Right. I think also Tommy Blotcha, I have to give him some of the credit, the initial idea for him, something about, you know, the robot pimp. We shared an office together, Tommy and I. But then I did write, yeah, the initial thing and his whole, the name of him and his whole persona and everything and the rhyming and all that.

His whole shtick. I remember I read Pimp by Iceberg Slim to get some, you know. Oh, right. Some ideas and background. Some verite. Some other similar literature by this guy,

Donald Goines, like, you know, these books like Whoreson and, you know, all these like inner city kind of 70s right yeah literature wow you really did your homework i remember once we had uh this show sold the lost in space the original lost in space i don't know if anyone even remembers yeah yeah

sure but the the original dr smith was on our show. Because Conan, especially in the early years, would have a lot of actors from hit 60s shows. And it was kind of like people you hadn't heard from in years. And one of them was this guy, Jonathan Harris, who was the original Dr. Smith. I think during his interview, the idea was Pimp bot would come out and yeah you bubble-headed boobie you get out of the you bucket of bolts right so we went in to talk to him before the show and conan you know was like oh you know your show was on in reruns when i was a kid and i watched every episode he's

like of course you did he was just like over the top flamboyant and we went over the sketch with him and he's just like of course i've got it yes of course i'm a professional broadway you name it i've done it and we're like okay this is gonna be great and then he's out there on the couch with conan his interviews winding up and then you hear like the mechanical noises and and pimp bot comes out and goes i get out something like hey dr smith you know and jonathan harris just looks at him and goes oh what a lovely fellow like he didn't do it totally forgot yeah literally in the 10 minutes that it lapsed forgotten there was going to be all his training and yeah and conan's like wow dr harris it's a robot who's his training. And Conan's like, Dr. Harris, it's a robot who's a pimp.

And he's like, oh, charmed, I'm sure. Like he just... And so the actor playing the robot is still doing the moves. He was vamping. He had to keep making his moves for like 20 minutes, just waiting for that.

You still hear all the servo sounds. So were these sketches that you were proud of? Like, did you tell your family? Yeah, hey, look, you guys got to watch tonight. The Masturbating Bear is on. I don't think I did. i don't think i did i don't think i did i think i yeah you had another bit on that that you could tell your parents about and uh no that is it's one of my favorite bits and they they put it i i think team coco put it

up a year ago and it kind of got all i think a lot of new attention it was uh the fbi sting sketch i love this one. Yeah, that was a fun one to do. A sketch where Conan's brother is in the audience and Conan introduces him. And it turns out his brother was a felon who was on the lam. And the FBI agents arrest him. And then it turns out the entire Late night with Conan O'Brien show that had been on for like three years already was an elaborate sting to capture

Conan's felon brother by luring him to the studio. Yeah. The sting operation sketch. Yeah. That was a fun one. And then it ends with them like completely dismantling the set and they dismantled the whole set. And the great part is Conan,

everyone who works on the show was in on this sting operation, except for Conan. Right. From the very beginning, him getting the job and everything was just to lure his brother out of hiding. He's like,

my brother's in the audience today. And then, all right, let's get him. And then Andy's an fbi agent everyone the you know they're all it was all just to lure this guy and what do you think you you'd get it you never seems weird that you got a show you know so everyone left everyone they they literally took this the set out yeah and then everyone files out of the studio. Yeah. And I think they took away the debt.

They took everything away. It was a bare bones place. Then Conan just appears in like a spotlight, I think. I remember like in, you know, by the monologue area, there's kind of just a light on him. Like there's one light left, his dress is dark. And he starts making some really heartfelt speech about, you know, maybe it was just this thing. But, you know, maybe I made someone laugh. And, you know, I had a dream. It's an important thing.

And then while he's in the middle starting to do this, you know, you just hear from the rafters like a stage. And it's like, ah, the idiot still thinks people are watching. And you just hear everyone just laughing at him and he just you know does his like thing of ultimate shame conan and runs away into the darkness which is which is great and then it goes out to commercial on that yeah oh that's one of my favorite things about it like no band kicked in like you know more conan in a minute it was yeah that commitment watching People watching were like, oh my God. Yeah.

Yeah. Complete desolation. Right. Yeah. I love then after that, he came back, you know, well,

my next guest, but I love that, that it never got deconstructed in any way. Was there a discussion at the time? I wonder about ending the, that night show with the sketch. Cause I would have been a, well, NBC was actually talking about ending the that night show with the sketch because i would have been a well nbc was actually talking about ending the series with that sketch hey you know this could do double duty we're never gonna have a better opportunity

he's giving it to us well i was wondering i mean we've you it seems like you've only had home runs on the show do you remember having any sketch that just bombed in rehearsal or something that you were like, this is going to do really well? I don't know. I don't remember anything like completely being, I don't know. I'm sure there were some that, you know, fell flat, probably because of technical problems. Yeah, yeah, yeah. Sure, of course. Oh, I do remember there was one.

It was kind of salvaged, but, oh, it was a kids' show. We did a kids' show. Right. Are you there for that, Sweeney? Yeah. Where the audience was all kids, and we kind of oriented it supposedly toward kids. Towards kids.

Yeah, and there was one, I had one funny thing on that, which was the boredom monster right which was like kind of this way to blackmail the kids through terror that if they're if they start getting too quiet at any point during this show the boredom monster's coming and we've cut to this this horrible monster in the hallway he was slithering his way toward them and they'd all scream and everything and it was was just this threat. Right. But there was a thing where for some reason I had this thing, a parade of birds came down in the audience. Oh,

right. Vomiting. Was it vomiting birds? Yeah. Yeah. I don't know if we said they were vomiting birds or I think it was just supposed to happen at some point, but they were all coming down,

you know, these guys in bird costumes, uh, down the alleyway and then at some point they were all gonna lean over and just projectile vomit on people in the audience i mean not real vomit obviously but with those you know snl type you know things which is still gross to have that it's still gross but not when it's birds but in the context of a bird parade come on right you're right yeah that's just like fireworks on the fourth of july it's what you expect with mostly a plant diet it's not that bad uh but there was some like huge malfunction and those were basically and then the birds leaned over and like nothing came out like this i don't know

whoever's who's doing special effects there was some kind of you know he's like pumping away or something oh no what's going on and like just like a trickle like of stuff came out and i was like oh my god that's just total and and then in like editing we were just able to put enough together that someone salvaged it. But in my mind, it was going to be like Exorcist gushing on people. And instead, it was just like a slow trickle. Look, a line of coughing birds. Yes. Like a mildly dyspeptic bird parade.

He's got hiccups. Can you, okay. So we kind of glossed over this, but what was the kids episode? What was the backstory of that? We were trying new things like in those days, like just,

you know, for the hell of it. I don't know. There was one week we did, which was time travel, time travel, right. Each,

each day that week, they Conan and Andy were in a different time period. Like they were... Ancient Rome. And then the next night, the Civil War. Right. And then this idea was just, let's do a show for an audience entirely of kids. And what would that...

Kids show. What would the show be? Right. As if our sensibility wasn't childish enough. Right. Yeah. We had to dial it down by two years. Right.

Hey, these kids will love Baghead. Right. Did the kids like it? Did the kids like it? I think they, yeah, I think they liked it. Yeah. Yeah. We kept them entertained enough.

My memory is no one remembered, I mean, no one anticipated them getting that restless that quickly. And then it was just Conan out there and we're all like, oh, good luck. Right. That's when he started string dancing. 28 minutes to go. Because there were no parents, right? In the audience. Like we just had.

No parents. They were like maybe watching from the green room or something. But the great thing was, my maybe you remember his name i think the second or third guest was like an nbc economics correspondent did we did we purposely book someone really dry yes and conan totally committed to it and they had this really straight dry interview. And I think the kids booed through the whole thing. Yeah. They just booed through the whole thing. I'm sure the boredom monster was coming out a lot then.

Yes. Yeah, it was fun to do these weird things once in a while. It was kind of a pain, usually, but good to get out of the rut, I think. Do you remember you were going to, I think you announced you were going to leave the show and you're, you're coming out to LA to work on a sitcom. So the head writer, Jonathan Groff started the search for someone to take your place.

Yeah. I've heard that this is a legendary story, but I'd like to hear Brian tell it. Yeah. Okay. I'll try to do it justice. But yeah, I hadn't been hired by a sitcom or anything at that time. I was just leaving.

I didn't know what I was going to do. But, you know, I was just like. Oh, wow. Kind of feeling, you know. You were like anything but this. Right. No, I don't know. It was still great.

But I was sort of like, you know, I felt like I'd done a lot. And so the search had begun and I decided to see if I could get hired again I mean part of it was like how much of it is just random like when you get hired or have I gotten worse right like you know maybe I'm not as funny like maybe I've you know maybe I've gone maybe not like, or it'd just be interesting experiment to see if I could get hired again. So I wrote another application, like I wrote a bunch of new sketches. Some of them were ideas that maybe I had had before, you know, while working on the show that never did anything with like, maybe they were too weird or, or maybe like, you know,

too annoying to produce or something like that, you know? So I never like propose them actually, but yeah, but I wrote, you know, a bunch of new sketches and I had, um,

now I just needed a front, you know, to hand it in. So you submitted those to the Conan show, but what was the front? The front? Okay. The front was a roommate of a friend of mine from high school named, handed in so you submitted those to the conan show but what was the front the front okay the front was a roommate of a friend of mine from high school named named hank flynn okay who was

like he was kind of uh i think he's he he's like a car you know he's an on-air reporter in philadelphia tv station or something now but he he did some stand-up at the time like some performance already stand-up so he kind of he wasn't completely from left field where you know so it wasn't like a shoe salesman he was doing some entertainment comedy stuff but uh he was a roommate of a friend of mine from high school and so uh he agreed to do it under his name and everything hank flynn uh and then i got g Greg Cohen, put it one step farther from me, Greg Cohen. Another writer on the show. Great writer on the show. Yeah. I was going to say that it was going through him, that Hank was

a friend of his or a friend of his friends or something like that. Oh, okay. So I wrote the thing up. We proposed, you know, we put it in everything and then the process began. And then it was like oh like finally how's it going you know and it's like well we we're down to a few you know whatever but and like hank flynn's one of the uh he's on the short list one of the finalists this is great oh and then uh greg cohen started getting really nervous by the way he just started having second thoughts like are we gonna oh this is really bad

like are we gonna get in big trouble actually as it when it got down to the very end we're like the two finalists i actually was brought in like like i guess groff and conan were like gave it to me like well you you look at these what do you think oh to weigh in yeah i did not want to i didn't want to spoil the immaculate you know the experiment so i just played it very neutral i was like i don't know they're both you know it's a toss-up to me you know because i didn't i didn't want to solely right you don't want to tip the scales one i didn't i didn't want to i didn't want to so i kind of stayed out of it it'd'd be like becoming a host of Jeopardy. Yeah.

Right. But then it was dragging on for a while, and Greg started getting really nervous. Yeah. That's getting a little dicey. Yeah. Yeah. And Greg was just, I was like, just hold on a little more. I forget.

I had some end game. Hang in there, Greg. But he just started getting more and more nervous you know and so they went for hank flynn right and he came in for an interview and he did fine whatever and then uh but how did you know he would do well in the interview um i don't know i mean i guess maybe i coached him a little bit, but you know, it wasn't like, he just had to not be crazy. Yeah. He just had to, yeah. Not be too crazy and everything. I think, I think like they liked his packet the best and everything. And also this guy was cool. He wasn't like, Oh, can I actually get this job? Do I get to work there? Well,

I found out later actually from my friend that he actually was like what if i just should i take the job what if like i think he actually thought at some point maybe i can you know scan the scammer and like somehow if i do well in the interview i mean what's right wait so was he interviewed by jonathan groff and conan i don't i don't know if conan was in there but he probably like did a phone thing or something with Conan. I'm not sure. But Conan was definitely on board with hiring him. Conan had read it too and everything like that. But okay. So I think initially when Hank got hired, I was going to have Hank come in and take the job and be weird basically and do all sorts of weird shit for like the first week you know and just

have all sorts of crazy stuff going on wait your dream was for him to actually take the job yeah just for like a week or so come in and just and then let the cat out of the bag you know so we pulled the plug early and how we did pull the plug was i think john actually had all of us come into the room when he was going to call hank flynn to hire him i remember this part we were we were in a meeting uh-huh and i think you it came up naturally but i my memory is you said hey are you ever going to hire someone to take my place sorry he's like like, funny you should say that. We settled on this guy, Hank Flynn. Right.

This is my memory of it. And none of you knew that this was all happening, right? No one knew any of this except for Greg Cohen. Yeah, yeah. So Groff goes,

he goes, you know what? We're all here right now. Why don't I call him on speakerphone and offer him the job? Oh, man. You know,

it's always a big moment when you offer someone a job. So it seemed very spontaneous. That was my memory of it. And so he calls Hank Flynn, and all the writers are in his writer's room. And it's at like 9.30 at night. And he puts him on speakerphone. Yeah. Although I wonder how much was organic

and how much did I press Groff to do it. Maybe a little of both. It worked out perfectly because I did have Hank Flynn record the phone call, so I actually still have a tape of that phone call. Hello? Hey, I was trying to reach Hank Flynn. Hank? Yeah, Jonathan Groff calling from late night.

Hello, Jonathan. How are you? Good. How are you doing? Not bad. Thanks. What's going on? We'd like to offer you a job.

Really? Yeah. Wow. Nice, man. Thanks a lot. Yeah. Yeah, we liked your submission the best. Well, thank you very much.

I had a meeting with Conan O'Brien a while ago, and Brian Rich is actually the guy who's leaving, and he'd read through the package, too. Wow. Yours was the best one. Oh, Jesus. See everybody on speakerphone. You just make me feel really good, man.

I really appreciate that. Hang on one second. All right. Everybody on speakerphone. All right. Hey have a good moment. All right. Hey! Hey!

We're not even ready to shoot. The bad part is we're at 10 o'clock at night, which is indicative of the nightmare that is this job. But other than that... Congratulations. You're racist. Thank you. Oh, Jesus. Jeff Ross is the producer.

I just talked to him, and I'll call you tomorrow with, like, more details about what you need to do. Okay, cool. Jonathan, actually, can I talk to just you and ask you a couple questions? Oh. What's up? Hey, I just wanted to ask you a couple questions. Sorry. I just, what hours do you guys usually work anyway?

We work like 10, 30, depends, to like now or later. Oh, really? Yeah, it's pretty grueling. Oh, all right. Because I got, it's just that I've got like, I'm sort of a regular on these open mic circuits, things that I like to do, and it would really hurt me if I had to give them up at all. You know, and that realistically...

You're probably gonna have to give them up if you want to do this. I see. Just because it's kind of, you'll be here almost every night. I mean, the only exception would be, would be like Monday, maybe we'd get out a little earlier on Fridays, but generally we're here until now or later. Right. So, what was... You know, three nights a week, sometimes four. What was Brian making when he left? I don't know.

Just because I think that the work is really I don't know. Just because I think that the work is really good. You know? I think that the work is really good and I just want to get what it's worth. Oh, you're not going to

get more than that. Right. Oh, okay. I mean, that's just sort of the way it works. Okay. I hear you. I don't want to hold you up.

Why don't we talk tomorrow? Okay, well, here. I don't want to hold you up. Why don't you and I talk tomorrow? Okay, well, here's the thing. Yeah. I was watching, I watched the show a lot over the past week. And, you know, some of it I liked a lot. But other, you know, some of the other stuff that just wasn't, I don't mean this personally at all, but some of the other stuff that just really wasn't much payoff to it. To be perfectly honest with you, I was watching The Daily Show today.

Do you know that show? On Comedy Central. And I think that maybe that's more the place for me. You know what I mean? You know what, Jonathan, I really appreciate you thinking about me, and I really appreciate what you think about my work. But honestly, I really think that maybe Comedy Central is a better place for me. Oh, okay.

Is that something that you're going to do? Well, maybe. I mean, I don't really know anybody over there, but I think I might be able to swing a PA job over there. But, yeah. I mean, I just think it's more my speed, you know. But thank you very much. Okay.

Okay. Take care. Okay. Okay. I'll take care. Bye. Oh, my God. So do you remember, did I reveal what's happening right then? Yes. I did. Okay.

That's good. Brock probably didn't believe me at first, right? We couldn't believe you would sit down and write a new submission. Go to so much work, yeah. Right. Knowing how hard it was to get me to write anything when I was actually being paid for it. Right, right, right. We were just

like, ugh, all that extra work. What was he thinking? Yeah, no, everyone was stunned. It was a great... And did people react well then once they knew? Oh, good. Oh, yeah. No.

Yeah. Just so you would pull that all off. I know. It's unbelievable. We were like, well, wait. Well, who's that guy on the phone? And you're like, he's a friend of mine, a roommate of a friend of mine. And just all the steps that went into setting up this phone call that night where everyone was kind of it was blown

away and then i think we we kind of reproduced it for conan with like i think we didn't tell conan what happened so there was another phone call where groff and i were in conan's office and i think groff got conan to have a conversation with the guy oh with hank i didn't try to convince him to come aboard or maybe groff act like he hadn't told so so i think hank did kind of repeat performance for conan oh wow let conan get a gut punch of this guy rejecting him as well oh my god and then of course then you know conan had got his revenge on me yes your last night right oh yeah so what happened it was your last night. Right. Oh, yeah. So what happened? It was your last night on the show, and I went to Groff and Conan, and we came up with this idea where, because back then, sometimes Conan, if a writer was leaving, he'd say kind of a send-off, like, oh, you know, so-and-so's moving on, da-da-da-da. So we're like, oh, what if he does that for Brian's last show at the end of the show and says, you know what?

Let's he's so great. Let's bring him out. And we bring out Hank Flynn. So we snuck Hank Flynn into the, into the building. And I was worried you were going to see him during the show, but luckily you were up in your office. So I don't know what you thought when you saw that.

Cause Conan goes, you know, there's a writer's been here. Let's bring him out. Brian Rich. And then Hank Flynn walks out. And were you watching from your office, Brian? Yeah.

So I was upstairs in the writer's floor. And I think, you know, I guess the other writers knew what was going to happen. Because they were like, come on. I think Conan's going to say something about you. You've got to see this. So I was in there with a bunch. I think you were probably there, Sweeney. it was yeah i was there yeah it was that office you who was in there you and kyle and brian kyley yeah kyley you know conan starts with his spiel

like you know this writer leaving and i'm all like i've been getting the warm plugs he's like oh this is so sweet he's saying something about me. Brian Rich, come on out here, Brian. And Hank Flynn comes out. And I was like, what? I was like, I was like, really, I was really upset because I was like, oh my God, everyone who ever, who I ever told I'd write for this show or whatever, like they're going to see this and be like, that isn't the same Brian Rich. Like, that's a completely different guy. Oh, wow. So I was just, I don't know. I was just definitely, yeah, it got me good.

I was trying to get down to the sixth floor and get up there and be like, no, no. Were you going to run out on the side? I was going to run out and ruin it so they couldn't air that or something. Yeah, I was going to run out there. Oh, wow. And people were like physically restraining me from getting to the stairwell and running down it. Like, we're going to put a bag over your head, Brian. You know what? No.

Now I remember why I was upset. Why I was really upset was because at the end, Conan, in the interview, when he's talking to Hank a little, what's next for you? He said he was going to work was going to write for Suddenly Susan. That's right. And I was just like, no, that cannot stand. That could not be a worse fate for me. Yeah, that could not be my trajectory. Well, it did stand.

Yeah. And I did end up working for Suddenly Susan for many a year. Well, as long as Greg Cohen was, he had to feel great relief when it all came out. You got to have, you should have Greg Cohen on this. I know. And Hank Flynn. Well, then we started using him in sketches after that. He was in a lot of. Oh my God.

That's right. So we did, he did actually get on the show after that he was in a lot of oh my god that's right so we did he did actually get on the show after that yeah he'd act in like a lot of satellite tv channels and stuff that's right well thanks for doing this yeah one thing we do we always like to wrap up the show by asking people for a piece of advice if they have one oh just keep at it guys you'll get this podcasting thing down eventually seriously oh that's sweet uh sorry no yeah i mean um a piece of advice let's as somebody who has been hired on the conan show twice now for somebody out there who might want to get a job writing in late night or you know have broad interests which you know you either have or you don't so I don't know if that's advice but I think you can you know find a way to use

like everything that you ever learn in running for you know especially late night and sketch and something like that that's like one of the things that's so great about it you know because you can just draw from anything you know or interested in and find a way to make that funny and get that across to people right that's a good one i don't know that we've covered that before but i think especially having specific interests and like the more specific or the more kind of detailed you can get into something that's gonna get you a lot of comedy especially if it's something people aren't as familiar with yeah and if you have a little you know a little knowledge that authenticity like kind of comes

through yep and like a sketch or joke like you just know like even if the person getting the joke doesn't know that much about it you can kind of sniff out like if the lingo and the right i don't know the background seems legit or something you know yeah like all the research you did for pimp bot exactly and your years as a pimp exactly i knew that would come in handy well thank you so much brian yeah yeah thank you oh thank you guys uh this mean, you're a legendary writer and it's really good to finally get to hash all these things out with you. Yeah, it's good to finally meet you. And that was Brian Rich.

That was Brian Rich. And Hank Flynn. I was going to say, with special guest Hank Flynn. Oh, that really, I can't believe that. I mean, it's. And you know what? Hank Flynn, I found out, is a field reporter on a news station in Philadelphia. Oh, how cool.

On television. Yeah. Wow. I kind of wondered what happened to him. I wonder if someone else actually got that job, but they handed it off to him and you know well i have to try to dig up that clip of him where where conan says goodbye yes rich but hank flynn comes out oh i loved that because i mean that was a that was giving brian a little bit of his own medicine exactly exactly uh try to even and and another boost for

hank that's right who really is an extremely talented actor i mean i was stunned by how good he played that because that was not scripted and he he played it perfectly no he he built that phone he just from the moment he said can you take me off speakerphone yes he and john and you know jonathan groff was great too he was yeah he was really patient he was just i think he knew like just don't react react i asked him about it and he said oh you know what i you guys were on the room listening so i yeah it totally inhibited me from like you know getting into it with him on the phone because i would have probably started crying he was stunned he was just stunned yeah the whole phone call

oh i'm so glad that there's a record of it yeah i know it's fantastic so that's the that's the moral of this story listeners is if you're to play an epic prank on your boss, please record it for posterity. Yes. Well, now everything is recorded. You don't have to worry too much. That's true.

Alex is doing it for us. I think now I'd like to ask people to record less. Yeah, that's true. We're running out of space. Just, just, you know,

sometimes memories are nice, uh, without the video proof. Uh, anyway. Oh, you know what? Last week we had a great guest, Jim Pitt, who is our music booker on Late Night and The Tonight Show and Conan for many, many years. And we got a great email referencing his appearance. yeah um the email i mean i'm going to kind of paraphrase here but uh our friend jed christiansen found out that a music analytics company called the next big sound did an analysis and they found that conan actually gave the biggest boost to bands out of any late night show yeah like in this back when letterman was on because i know letterman had a lot of musical acts too and they said an appearance on conan was a bigger boost for musical acts in terms of downloads of their music following the appearance even bigger than

yeah an appearance on letterman which was very impressive. Yeah, it says, Artists appearing on the charismatic redhead stage, on average, see a 50% increase in iTunes album sales and Facebook fans. Yeah, that's a nice thing to hear. The Conan bump. The Conan bump. Well, cool. Thank you, Jed, for writing in with that.

And we have another listener question. Yeah, here it is it's from santiago at santiago dot oval is there any sketch you regret not doing like an idea that got thrown to the bin because of it just says because of reasons well there's always reasons jesse do you that's accurate yeah because of it not being good enough or sometimes not i mean honestly i i did i was just remembering a sketch that we didn't get to do and i still think it holds and it was one that i had like i had set an alert for myself to pitch it again the next year. Because sometimes you could repitch things that didn't make it. But this one was, it was a Father's Day sketch.

And the premise was that Conan and Andy had both received a World's Best Dad mug from their kids. But there couldn't only be one World's Best Dad. So they had, basically it became a game show a father off and it was hosted it was supposed to be hosted by bob saget so i think that was the problem was that we we couldn't get bob saget that day um where they had to answer questions like uh you know how many hours ahead should you arrive to the airport right basically everything from that uh progressive commercial now but it yeah it was it was just like dad isms that they had to have a dad a dad off that that sounds like a great sketch i think it could have worked sweeney and when you what and even when you repitched it it didn't it didn Well, then I think I just forgot to, or maybe it was like the next year it was, it might have been that the next year was COVID and we just didn't.

That old excuse. Like my sad little alert came up and then I was like, oh, we can't do that now. Someday you'll get to, I feel someday you'll get to do that. If there's still a Father's Day, who knows? And if there's still a Bob's day who knows if there's still a bob saget fathers are becoming obsolete there will always be a bob saget i i remember a sketch where literally we just ran out of time it wasn't a sketch it was do you remember Shia LaBeouf? Yeah. I mean, he's always sort of in trouble. But back in 2014, I think he made a movie and was accused of plagiarism.

And then he did a whole art installation where you could visit him in this art gallery and sit alone with him for seven minutes while he wore a bag over his head. I remember that. That said said i am not a celebrity so that bag was a premonition right yes it really was i i hope he bought bought them in bulk so i i forget whose idea it was but the idea was uh trimeth insult comic dog would go and confront him for seven minutes and we'd of course shoot it and i but i think the idea came up late so we really didn't get on the line we got on the line the last day oh but you actually went well i showed up and And Robert Smigel We had someone waiting on the line And then Robert showed up

And took the person's place on line But time was running out And then I think we were trying to bargain With the people in front of us Like, come on, man It's Triumph And, you know They were all filming other late night shows

Right, exactly Come on kimmel you know let us do it it was a thing where we just ran out of time and they they closed the exhibit and but it would have been problematic because you weren't allowed to shoot the video in there yeah so we had to cheat we had secret cameras set up but then i don't even know if we'd figured out how to shoot we'd have to get someone else in the room with him to shoot but he obviously we need a shot of triumph and and and interacting with shia so right i don't know it was definitely going to result in an arrest so but i but I was always, I was always, I would just love to have seen them, those two together. That would have been great.

Yeah. Well, yeah. Just like the more time that elapses, if you watch that now, you'd be like, wait, what is. Why was he doing that? Why is he killing out a man with a bag on his head? Well, maybe we'll see it someday. Yeah, maybe we can combine it with the Father's Day idea.

Oh, yeah. They're both probably parents. That'll be our make-a-wish. Trimes fathered hundreds of children. That's probably true. Yes. Well, thank you for that question. And you know what?

I have a note from our producer that we're running low on listener questions. That can't be true. I know. I'm stunned that you guys are out of questions after all this time. But so if you have one,

there's a really good chance that we're going to read it. Yes. So you can email us at insideconanpod at gmail.com or you can leave us a voicemail at 323-209-5303 um oh and the the live conan o'brien needs a friend episode recorded at the wiltern theater is going to be available on team coco podcasts uh for anyone who was not there in person yes see you next week yes thanks for tuning in. Thanks for listening. We like you. Adam Sachs, and Jeff Ross at Team Coco. Engineered and mixed by Will Becton. Our talent bookers are Gina Batista and Paula Davis.

Thanks to Jimmy Vivino for our theme music and interstitials. You can rate and review the show on Apple Podcasts. And of course, please subscribe and tell a friend to listen to Inside Conan on Apple Podcasts, Spotify, Stitcher, Google Podcasts or whatever platform you like best It's the Conan Show Put on your hat It's the Conan Show Try on some spats You're gonna have a laugh

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