Inside Conan: An Important Hollywood Podcast - Conan O'Brien & Jeff Ross Look Back

Episode Date: June 24, 2022

Conan O’Brien and longtime executive producer Jeff Ross join writers Mike Sweeney and Jessie Gaskell to discuss Conan and Jeff's first meeting, the start of Late Night, Tom Hanks’ message to Conan, and the fate of Conan’s Ford Taurus.Watch Stay In Your Seat Theater here.Watch footage from Conan's test show (including the "crank" moment) here.Got a question for Inside Conan? Call our voicemail: [phone] and e-mail us at [e-mail]

And now, it's time for Inside Conan, an important Hollywood podcast. Hello and welcome to Inside Conan, an important Hollywood podcast. I'm Mike Sweeney. I'm Jesse Gaskell. We're writers for The Conan Show, and this is Inside Conan, where... We go inside of Conan, the show we wrote for. Yeah, exactly. We've gone behind the scenes, especially this season, kind of starting back in 93 and doing

an overview of Conan's many years on Late Night, 28 years on Late Night. And this is our last episode of the season. Yeah. We've caught up to the present. So he has to make more television history so that we can make more episodes. Yes. And we're not going to end this episode just to keep the pressure up on creating more content. That's right. We're going to keep talking until we get the deadline article announcing his next move. Exactly. So we both have food and we're going to sleep while we do the podcast. We'll take turns.

I have a little mason jar to pee into. Yep. Yep. I have a big one because I have a smaller bladder and we will stay on the air until there's new content to cover. That's right. I'm sure this pressure tactic will work with Conan. If he ever hears about it. He'll be the last to know.

You know, I got a message from somebody on Instagram. Because we joke a lot about what if there was somebody listening who had never watched any of Conan's shows, but listened to our podcast? Like that, that person doesn't exist. Right. That person does exist.

And she messaged me. Yes. And she said that she had never seen anything Conan's ever done on television, but she listens to this podcast. Oh, wow. And so she's learned about it retroactively. I know.

What if she watches him and goes, oh, this doesn't compare to the vague descriptions of these bits on a podcast. And they're visual. Ugh. Why would anyone watch this? Yeah. Really? Where does she live? I'm just curious about this person.

She is from London. Okay. But she's moving to Los Angeles. Oh, wow. Yeah. I'm a little suspicious of this. She listens to the podcast, but she doesn't have Google. Or she doesn't want to watch.

I think she doesn't care to. All right. Okay. I think it's a personal choice. Oh, wow. All right. No, I loved it. I thought, oh, this is great.

It's fantastic. Exactly what my ego needed. Yeah. Well, we are really dancing around the elephant in the room, or should I say the dog puppet in the room? Oh, yeah. That big news. There was big news. Robert Smigel, who we've interviewed three times now on this show.

Yes, the most of anyone ever. The three-timer club. Yeah. But he's been on more than you and I. Exactly. And Triumph himself was on our show for the 100th episode. He went to Shreds, which delighted me. Yeah.

Well, they were all, I mean, I think people know this pretty big story, arrested in one. Yeah. In one of the Capitol office buildings a few days ago. While they were filming a remote. For the Stephen Colbert show. Yeah. I feel like, I mean, we almost got arrested a lot of times. I know. A few times. There've been some close calls.

Doing Triumph for Conan. Yeah. There were close calls. So it's kind of surprising it took this long in a lot of ways. It is surprising. And, you know, everyone likes to tell their triumph stories, but now this gang that got arrested with Triumph has the best... I mean, getting arrested is...

Oh, I know. Yeah. I don't think anything tops that. It's a lot of cred. Yeah. I mean, Robert is... He's the Werner Herzzog of comedy he he he has to get the shot he has to get that boat over a mountain sometimes not all the times but

sometimes and he usually he gets it but it's it's it's very impressive and yeah but this wasn't the westminster dog show right i think it must have been different doing it at this place where there's a lot of people who maybe want to use this for their own political gain and of course the capitol police now are you know they yeah they're on alert they were the mutts last year after the uh you know, insurrection. So they have to. Right. Now, you know, they see any puppet in the hallway. They've got to arrest it. Exactly. And as we record this, there's been no response yet.

There's a Colbert show tonight. Yeah. I'm really curious how he's going to address it, if at all. We should say we've heard from Triumph and the crew that they're okay. They're okay. But they can't talk about this incident because it's an ongoing legal issue. But Triumph could talk about it because he's a dog. You're right.

I mean, unless they processed him as well and arrested him. Oh, I would really love to see a Triumph mugshot. I'd love to see that. I'm sure there's some out there somewhere. Yeah. So Triumph maybe might appear. Who knows? He could appear on Colbert.

And Robert could play his lawyer, Alan Dershowitz, I was thinking. Because Robert does a great Alan Dershowitz. I bet he does. Yeah. And that would be a great Robert Triumph bit where him going back and forth with the two voices. Yeah. Yeah. Yeah. Okay.

Well, I hope you pitched that to him. Believe me, I'm sure that occurred to him while he was getting stopped in the hallway. I'm sure he was immediately thinking, all right, well, now we have to shoot the dog getting conjugal visits in a jail. Humping some dogs. From a German shepherd. Yeah. Well, I'm glad they're okay. And how's, you're still working on your new job?

Yeah. I mean, it's only been a couple of weeks, but I'm really loving being back in a writer's room. Oh, that's gotta be great. It's so fun. I really miss, I mean, I of course miss our writers in our room. Well, yeah. I mean, nothing will ever equal that experience.

It won't. It won't. Nothing will ever top that. And it's, of course, a lesser. And we're going to keep chasing it for the rest of our lives and coming up short. You're trying to get that initial high back. But no, that sounds great. So it sounds like a fun group.

It feels good to be, you know, back around my people. Yeah. Well, that sounds, back around my people. Yeah. Well, that, that sounds, I'm so happy for you. That sounds great. Oh, thanks. Uh, well I can announce today that I am officially signing up for the, um, Alcatraz shark swim. Yeah. Oh, I'm so glad.

Except for we won't have any more episodes. So we can't check back in to hear how it went. No. So that's why I'm announcing now. No one can tell whether I'm lying or not. No, that's great. Well, yeah. That's a big deal. Yeah. Yeah. I've been literally actually ramping up my training for it. That's right. And I've never trained for anything before.

I know you were having to do a timed swim right yeah and i i did like i swam a mile at zuma beach yesterday morning with wow these other swimmers who meet twice a week so that's my new instead of the writer's room i'm hanging out with um long distance swimmers hardcore swimmers they're hardcore swimmers and they're polite to my face. And then- Yeah, that sounds terrifying and cold, right? Well, I like the cold water. It's 66 degrees, which I don't wear a wetsuit. I'm good down to 62. Do swimmers sweat while you're working out?

I mean, is that a thing that happens? Oh, you know what? I guess. I don't know. Yeah. Yeah. Gotta go somewhere. Well, that's amazing. I'm so proud of you. Well, I haven't know. Yeah. Yeah. Gotta go somewhere. Well, that's amazing.

I'm so proud of you. Well, I haven't done it yet. I know, but you signed up. But you're proud that I'm verbally saying I'm going to do something. Yes. I think that was the harder part for you. Good job saying you're going to be an astronaut. That's what I feel like.

I feel like I'd say that I'm going to grow up on August 7th to become an astronaut. No, but it's so much easier to just quietly do something and then announce it after the fact. Yeah, well, that's called having intelligence. Only a moron such as myself announces it beforehand. What a jinx. What an awful, stupid thing to do. But you know what? Some of our friends also have heard about it and they like want to come and watch it which oh cool are there going to be boats going alongside where you could

i don't think it's like a flotilla i they just wait for you on the shore yeah but i don't know what what there is to watch there's just like yeah these dopes swimming in you know maybe if you'd see the three guys who escaped from there in 1960, or if there was a shark attack. Yeah. Now that's something. I'm not worried about sharks. A lot of people were worried about- I would be worried about sharks. I feel like my meat is probably pretty rancid by this point. So I feel like I'm-

A lot of gristle. They should hire me to swim. I feel like I'm good shark repellent. So I'll protect everyone else around me from shark attack. I would draft off of that. So this whole season has been a retrospective of Conan's late night career. And we did want to come up to the present, but in order to understand the present, you have to understand the past. Wow. So we asked Conan and his executive producer jeff ross to come on together we thought that would be interesting to hear yes about their relationship because they've been in a professional relationship for almost 30 years now yes uh it seems pretty productive and healthy and you know

what i i everyone was like oh i don't think they've ever been in the same room together talking about it's one or the other. But then once we got them on, and I kind of thought, oh, you know, we'll get to hear about the whole arc of their relationship. But we really didn't get past year one. I think we covered three days in their relationship. There was a lot to say. And I think Conan really got into reliving it with Jeff there to confirm. Yes. Jeff ended up nodding his head a lot.

Like, it's true. That's what happened. He did. You won't hear him nodding his head, but just imagine that he's doing that. I think the details of their origin story are seared into both their heads and minute details. So Conan was like, okay, you want to hear about how we met? Check this out. And it's, they were great stories. It's amazing. But it's great. I know.

Yeah. So without further ado, here is Conan O'Brien and executive producer Jeff Ross. I'm Conan O'Brien and I'm here with Jeff Ross, longtime executive producer. Came in, what, 2007, I think he came in. No, that's a joke. He started on the show before you did. Jeff was there before I was there. And we have agreed to be on Inside Conan. Thank you.

And this has been a year-long negotiation. It's been a lot of back and forth with lawyers, publicists. I wanted to make sure that you had spoken to every prop master who ever worked on the show. Before you got to me. Every custodian.

We've talked to both of you. Separately, but never together. Now we're here to compare your stories. I don't think you've ever been in the same room for an interview before. It's a terrific idea. I think we have. Jeff is not. I think it's a Friday and you're like, no, no, no.

Rather, you want to start your weekend. This is just another sandbagging by Mike Sweeney. I have. I wish I had an agenda. I wish I had that. First of all, Jeff, you just got back from Cabo. You've been away for a week. What?

Yes. And he's acting like I've got to get back. Exactly. And he's already like, what am I doing here? I got to get out of here. He has his own tequila now. It's a subsidiary of Cabo Wabo. It's called Jeffy Weffy's Cabo Wabo.

It's actually called Conesy Wonesy. Conesy Wonesy. Conesy Wonesy. We're not promoting that on this podcast. Well, you just did. It's a good idea. And that's not coming out. That's how we pay the bills.

Only CBC products. But yeah, so we're here and we're open to this examination. This is the Warren Commission on Conan O'Brien's career. I'm getting the impression you two never talk to each other. How could one bullet do that much damage? We just passed the statute of limitations. So now you can't be prosecuted for anything in those early years. Yeah.

Well, maybe we can start at the very beginning. What were your first impressions of each other? Well, we should tell the story that how you met. Yeah. Because and then I'll set it up and then, Jeff, you can take it away. Basically, to take people way back when in the way back machine, David Letterman announces he's, because he didn't get the Tonight Show, he's pissed. And he's angry. He feels like that he was in line for that.

Jay got it. Forget his last name. And so Letterman's upset. And then he does the thing that NBC doesn't see coming. He says, I'm out of here. Yeah. And they never thought he would do that, I think. And so suddenly

uh there's an opening they need a host for 12 30 and at the time people don't understand now now i mean there's no such thing as a time slot anymore really but there's just an infinite number of jobs now and shows back then when a when there was a space available it was like a once in a decade event, especially in late night. It was a big deal. It was a huge deal. And everyone was like, who's going to replace Dave? And the affiliates were getting nervous.

So NBC had an idea, which is to stall and to keep the affiliates calm. We'll just tell them Lorne Michaels is going to figure it out. The producers are starting out live and he always makes the right choice. So Lorne will do it. And so Lauren agreed to that, I think, you know, and with the understanding that he would produce it and that bought NBC some time with the affiliates. They're like, whoa, oh, good, good. Well, Lauren is figuring it out. It's being handled. It's being handled. And so then. And that's great shorthand. Oh, it was a very good idea on um and nbc has only had good ideas this was a incredible team of brain trust and then they um so lauren's handling it and then lauren's first move

before he picks anybody is he knows a young lad named jeff ross and he dials the phone. Jeff, fresh back from Cabo, even back then. Oh, man. Trashed on tequila. No, no, no. Not at all. And by the way, this is a six-hour episode. It's more like a rectal exam. It won't be that pleasant. Those of you who get medication from Mexico.

I love a rectal exam if I get the roprophyl. Phone rings, and Jeff, you take it from there. I'm leaving. Lauren says to me, I guess it was in the news. We all knew he was going to produce the show and pick the host. And he says to me, would you produce it? And I said, well.

How did you know Lauren? Oh, I'm sorry. Well, that's true. That's a good thing I'm here. That's called a follow-up question. I had spent a year in Canada producing the kids in the hall. And then I was doing some other shows for Lauren, a lot of HBO specials. And I was around and Lauren knew me. And I guess he just hired somebody to do something on this thing. So he called me and he was like, so, you know, I'm doing this thing. I got the I got to find the I got to produce the show to replace Letterman. I go, I heard. And he says, you want to produce it? And it's sort of to what Connor was saying. It's such a surreal thing, you know, let alone, you know, obviously you want to be the host. Somebody says, you want to produce the show that that's going to replace Letterman,

which was the biggest thing at the time. And there's no idea who the host is. So I wound up in this sort of like crazy whirlwind of nutty ideas and going to auditions. I think at the same time, he was talking to you. He talked to you first, because I knew I had heard your name. We hadn't met yet. We hadn't met. And Lorne, I had left SNL two years earlier,

maybe two and a half years earlier, and gone to the Simpsons. Right. And so I was in Los Angeles and I had moved on. Lauren very sweetly had really wanted me to stay at SNL. And he was saying, you can work from home. It was really nice. Wow, he was ahead of his time. He really was.

He said there's going to be a terrible virus. You never have to come in, right? There's a virus in Wuhan. You're seen. You're seen. You know. there's and i said no i really have to go i was going through a lot at the time that'll be in my memoir i was going through a lot of stuff uh in my personal life and i was i think very unhappy and i just decided i've got to leave uh the east coast and so i i got this great chance to work on the simpsons so i I'm there. And I really feel like I've put New York in my rearview mirror. And I've put, even though I had an amazing

experience at SNL, I thought that's all behind me now. And then it's now two years later and the phone rings and it's Lorne. And he said that he's setting up the new late night show to replace Letterman. And I'll remember very clearly me saying, well, good luck because there's no replacing Letterman. And I was quite sorry for whoever gets, no, no,

I really just show a test pattern. And I think Jeff probably felt the same way. We both felt like, I mean, he had been, you know, Dave had, you know,

recreated the talk show and, and created this whole new sensibility. And it felt like, you know, recreated the talk show and created this whole new sensibility. And it felt like, you know, he had discovered this whole new continent. How do you follow that? And he had carved out 1235. Is this? Yes. I actually thought it wasn't really going to happen.

You thought what? I just thought it wasn't going to happen. What do you mean? In other words, either Lorne wasn't going to produce it or, you know, something was going to happen and I wasn't going to produce it. Right. So it just seemed not real at the time. Did you hesitate to say yes to producing this show? I said, yes. You just jumped right in. Okay. I didn't believe it. Okay. And I, and, and so Lauren at first is talking to me about being the kind of head writer, you know? Right.

So Jeff will be the producer who makes it all happen. And then I'll be the head writer sort of producer. And I remember initially being like, well, I'll talk to you about it. First of all, I had a contract at The Simpsons. Right. That technically wasn't breakable, which sounds crazy, but- Fox is hard. They don't- I'm not kidding. Yeah, I've heard that. That's later on in the storypsons. Right. That technically wasn't breakable, which sounds crazy, but- Fox is hard. They don't-

I'm not kidding. Yeah, I've heard that. That's later on in the story. Yeah, I had signed like a four-year deal to be at the Simpsons, and I think I was doing a good job, and they liked having me there. So this is not a place,

not the Simpsons to be specific here. Fox is not a place where you can just say, you know what? Right. I'm out of here. Yeah. And so there was that. And I also kept saying,

I don't think anyone can replace Letterman. I mean, I was saying that and thinking that and actually still believe it. I've seen no evidence. No, I'm not kidding. I still think that's the case. Case closed. But so Jeff and I are,

I think we maybe, we didn't talk yet, but then at some point I, we hadn't met yet. Right. Jeff's just a name. And then I bow out. I say, you know what? I remember having an anxiety attack, a really strong anxiety attack.

Right. And thinking, I just can't do this and i called lauren actually went and met lauren who had an office at the time at the paramount lot and i just said i can't do it and he was i think a little rattled because he i think was telling people i've got this lined up i've got jeff i've got conan he's trying to put the pieces together he's trying to put the piece together it's an anxiety attack just on being the head writer of this yeah and you don't and you don't know who Yeah. And you don't know who the host is. And I don't know who the host is.

And so I bow out. And so I'm out of the process. And I remember feeling a huge sense of relief. Huge relief. Yeah. Then a couple of weeks go by. And Lauren, I think, had a showcase. And I think Jeff went to the showcase.

Well, I was on the East Coast doing another show. And I had to go, come to LA to do a different show. And Lorne calls me to his office, the same office at Paramount. He says, well, can you go to this showcase tonight

at the Improv? Uh-huh. And we've talked about this before. It was like, you know, it was like five comics, all male, I believe. And they all knew that they were auditioning for Lorne.

Oh, yeah. Oh, yeah. Lorne was there and so were the guys who were in the network. Don Allmire was there. Warren Littlefield was there. John Agolia was there. He was like the business affairs guy.

And afterwards, what was the restaurant? Those guys are always good laughers. Remember the mustache? Oh, yeah. Remember the mustache cafe? Biz affairs. The mustache cafe. It was across from the-

I remember the mustache cafe. So afterwards, they're all going to us. And Lorne goes, come with us. And I'm thinking, this is, it's crazy. Yes. I remember the mustache cafe. So afterwards, they're all going to us and Lauren goes, come with us. And I'm thinking, this is, it's crazy.

Yeah. And we go over there and I'm sitting there and he goes, well, and everybody's

arguing about who they thought was good and who was not good. And Omeyer goes,

everybody meet in my office tomorrow. And Lauren turns to me and goes, can you come to this meeting

at Omeyer's office? And I go, sure. And so I go to this office and this is when

the connection started. With Conan. Omeyer's kind? And I go, sure. And so I go to this office and this is when the connection started. With Conan. Ohmeyer's kind of beating up on everybody. Uh-huh. Because that's kind of the way he was, you know. Yeah, he was,

Don Ohmeyer, you all know him, but he, you know him because he was running NBC when the OJ trial was happening. And Don was very good friends

with OJ and would get very upset when Norm MacDonald would do jokes that basically said, for reasons I don't, because I don't see the evidence. But basically say that, I mean, on the day of the verdict,

Norm MacDonald said, well, it's official. Murder is now legal in the state of California. So that really didn't endear him to, this is just to tell you who Don Ulmeier was, but Don Ulmeier was kind of like, imagine Babe Ruth at around 45 years old, like a big over the top. And I have a lot of affection for Don.

I want to make that clear. I really do. And I think he had a lot of really good qualities and he was very loyal to me in the long run. So there's a lot of things about Don that I have very good feelings about.

But he was, he could sometimes, he could be very intimidating and be kind of, he had a sports mentality because he had come from the world of sports. So it was a lot of like

kicking guys in the ass and get out there. Come on, you got to figure it out. Get your head in the game, you fuckers. And it was that kind of attitude. So he was sort of

putting everybody on the spot to come up with and Ludwin was there and Rick Ludwin. And so finally, Lawrence says, well, I think Conan could do it. And he turns to me and says, don't you think? Oh, wow. And that was the first

time he'd brought it up. He had not met. He had never met me. And so I smartly go, yeah, I think so. That's how you survive in show business. Great improv skills. And I'll never forget this. And then Omar goes, well, can we test him? And then Lauren turns to me and goes, can we test him?

And I go, sure. So what happens is I'm working at the Simpsons like a normal everyday Joe. And I come home with my lunch pail and my hard hat and I put it down and I see that there's a machine. The machine is back when you had a machine with a blinking light. Let's explain what an answering machine is. Yeah. And so I play it and it's not, Lauren doesn't leave messages to this day, but it's one of his 35 people saying, Conan, could you give Lauren a call? So I call him and he said, look, I know you don't want to do it, but would you be the head writer? But would you be interested

in going to an audition? Now I had a panic attack at that, just the idea that I would audition because I was a writer. Now things have changed a lot since then. This is before, I mean, now Seth Meyers, John Mulaney, there's just this long tradition, Tina Fey, people are writers and then they get elevated and they figure it out. This hadn't really happened before. Right. Behind the scenes, I had been kind of a performing writer for a bunch of years doing improv, groundlings and improvisation. And constantly, that's where I met Lisa Kudrow. I started doing improv in 85. And so I was very interested in that.

But I was not a stand-up comic, which is really was considered, you have to be. It's like to drive a car, you need a license. What do you mean you're not a stand-up comic? That was the mindset back then. Yeah. And I remember it at SNL. I was Jim Downey was always putting me in things because I was the guy be is in a room full of writers trying to make everybody laugh and doing a dance for them or spinning out some wild thread. And so I think Lorne had seen me doing that. He had seen me cracking up Jim Downey and he had seen me play little utility roles and sketches here and there. And so the notion was maybe. So he talks to me. I'm very nervous. I call Robert Smigel. I can imagine.

Yeah. Robert Smigel's initial response was, you know, I wouldn't do it if I were you. Oh, wow. Now, listen. Listen, I'm going to say that. That was for your own sake, I'm assuming. No, but listen. To be honest, he was echoing everything in my head.

Yeah, yeah. It's what everyone would say. Yeah. He said, I wouldn't do it if I were you. And I said, and what's the reason? And he said, because that is a hard way to get into show business. Like you're a complete unknown.

The knives will be out. He said all the things that ended up to a large degree playing out. And he was telling me all that. And I was nodding. I remember this was a apartment on Cochran. No, I'm sorry. No, Beverly Hills.

No, I'm sorry. No, not Cochran. That was my earlier apartment. Johnny Cochran. I moved around more than like Ted Bundy. Bundy Drought. Yeah. Bundy once said to me before he was executed,

you moved around a lot. And I'm like, you know what? That's my business. But I was on Weatherly, which is kind of near the Four Seasons Hotel. Yeah, you could walk. So I remember being in this, I had this little, like,

I was a guy that didn't know how to furnish an apartment. I just wrote and ate out at Chinese food places at night and worked on my Simpsons scripts, you know, completely undeveloped male human. And I was in this little breakfast nook and I remember very clearly the table I was sitting at talking on this shitty little phone and Robert saying, I don't think I would do it. And I was like kind of agreeing. And in the background, I heard Michelle, his wife say, who's fantastic. And Michelle, I just heard her in the background go, what are you doing? And I couldn't quite hear

her. And I said, what did she say? And I heard Robert talk to her. And then he came back to the phone. He went, well, Michelle says, what do you have to lose? And then I heard in the background, Michelle was like, he should do it. What does he have to lose? He's funny. And I had this little like tremor of maybe. Yeah. What do I have to lose?

And then Robert went, well, that's a really good point. So I thought, well, what's the worst that could happen if I audition? I'm not going to get it, but I'm interested in this getting out in front of people. So that's when the next thing I know, I'm told by Lauren, okay, we're gonna test you. You're to go meet Jeff Ross at the Four Seasons Hotel, which in Beverly Hills, which was like a five minute walk from my apartment.

So I walk over, I get to the lobby first because Jeff's upstairs upstairs beauty regimen putting the cucumbers on his eyes he needed a spa yeah guilty as charged and i'm downstairs and there's a lobby they've changed the lobby of the four seasons now but there used to be this um kind of business desk that was made of lucite was like a clear plastic desk and i was sitting at that clear plastic desk just waiting and then je at that clear plastic desk, just waiting, and then Jeff comes off the elevator. We've never met. And he walks around the corner and goes,

and I go, Jeff goes, Conan? And I go, Jeff? And I go, yeah. And then I gesture to the desk and go, what do you think? I thought you went like this. Yeah, I kind of hit the desk and went, what do you think? And Jeff was like, I don't know. And I was like, yeah, I know.

So then we talked about it. We talked about how crazy it was, honestly. So the chemistry was off the charts. Yeah, right away. Right away. You know what I love? My first interaction with Jeff was disinterest and no faith in me and nothing's changed. He would have been looking at his cell phone if he'd had one.

There was no cell phone. No, Jeff used to carry a rotary phone. Jeff had a rotary phone in his jacket. Long cord. cord and he was it was always getting tangled to things i gotta check my messages can you unroll me so it's just it's just an example of how surreal the whole thing was you couldn't really believe in your heart it was gonna happen like you were probably both laughing yes oh it was yes and i have to say i was laughing at this. Yes. When you missed each other, right? It was clearly a lunch out of this. And I have to say, I was laughing at that point because

I took what Michelle, Robert's wife said to his heart, which is, oh, what the fuck? Just try this. It's not going to happen anyway. Right.

So, you'll probably regret not doing it. This story, I mean, we could do nine hours on this story and I'm trying to move it along, but long story short, Jeff starts to, with NBC's help, starts to put together kind of like an audition.

And the only space they have to use is the Tonight Show. It's always been good luck for me. So the idea is when Jay's done with his show, he's going to leave and the crowd's going to leave. They're going to bring in another audience and I will come out and do a monologue and then interview two celebrities. And I won't know who they are until I get to Burbank. Wow. So Jeff was putting it together and trying to find the celebrities and I had nothing to wear.

So at the time I called my best friend, Lisa Kudrow, and I say, Lisa, you've got to help me. And she says, don't worry, I can help you. So she took me to... Ooh, makeover montage. Well, it's hilarious. This is the worst makeover montage. But I had no one... You went to Sears.

Two thirds of the way through the movie. That's when they happened. We went to Best Buy. We went to the big and tall show. We went to Fred Siegel. Oh. Down near Santa Monica. And so I have a, this is, I have a 1992 Ford Taurus. I think you still have it.

Very proud of, that we still have, by the way, Jeff. You know what I can't believe? I know. It is, it's still on our budget. Oh my God. I think of the things that we store it. Wait, what do you store it for? I don't want it.

That's. It's, no, but I mean, it's paid off by now, isn't it? No, no, no. It's not the car. You got to store it somewhere. I'm storing it. Yeah, we bought a 50 year. I got on the 50 year plan.

It's not a house, Jesse. You don't get a mortgage. It could be. You could make it an Airbnb. You could be earning money with that car. So I pick up Lisa. We drive over to Fred Siegel and we go to, we're walking around.

Now, I now know things just from being in show business. I kind of know like, they should probably, they should put some makeup on me. But I also know kind of when you're my coloring, what are good colors to wear?

Like blues are really good. They make the old blue eyes pop. And they also, what colors really help if you are very, very pale? Redhead. The one thing I've learned that you're not supposed to do is wear very, very pale, like white. I should not wear that. So Lisa and I, together, we committed this crime together.

Like Leopold and Lowe. Individually, we would not have killed, but together we did. We pick out a white linen jacket. Oh. A white linen jacket and like a white shirt, I think. And I throw it in the back of my Ford Taurus, which by the way, I later found out has radiator fluid in the back.

Green radiator fluid, which got on some part of the jacket that I hid. But- I love that I hid. But, I love that that Ford Taurus was the car you drove to, to do this. So then Jeff sets this thing up and we're kind of talking back and forth. Yeah. Then I drive,

it's set up for this time. I drive to Burbank. And when I get there, you guys had worked it out. You had found Mimi Rogers, Jason Alexander, Jason Alexander. Right.

As guests. As guests. Yeah. And Jason Alexander, of course, doing, Seinf Rogers. Jason Alexander. And Jason Alexander. As guests. As guests. And Jason Alexander, of course, doing Seinfeld at the time. Seinfeld. And Mimi Rogers doing movies and she had been a model, modeled and, you know, and so Married Tom Cruise. Yeah.

Brief marriage to Tom Cruise, I believe. Worth mentioning. Yeah. And then my first time getting interview notes so i got research you jeff had arranged had asked nbc and they said yeah we have we can use the tonight show research so i was given research that they had on file for the last time jason alexander had been on the tonight show and the last time mimi uh rogers had been on the tonight show so i go in this office and i'm just looking and i'm scribbling out my monologue which i had been thinking about.

You had to write that? Yeah, I had no writers. Oh, my God. How far in advance of the taping was this? Hold on. What? What is that? Oh, my gosh. The Vikings are landing.

He didn't mute his phone. Oh, my God. It was like a horn. It was like a Norse horn. By the way, I want to use that to get that ringtone. I'm in the North. If you see the movie, I interrupt a tribal ritual with my phone. So please check out the North.

Please keep that in. So I like, I like, these are the best moments. Mike Sweeney's phone just went off and his ringtone is a Norse, Norse horn. He's been doing this for 25 years. How far, how much time before the taping was it? There wasn't that much time. Oh, this is maybe, the Tonight Show was it? There wasn't that much time. Well, oh, this is maybe, the Tonight Show was still going on when I got there.

They were still taping it, which might be, maybe they taped it, I don't know, five to six or something. Right, right. And so this would have been after that. I think our taping was gonna start at seven, something like that. I'm going over the notes.

I had come up with an idea for a monologue. It wasn't topical, which would sort of foretell the kind of comedy I liked, but it was all about the absurdity of me. And I remember the monologue was kind of, I think you actually can see it now, but I think I was very taken with, I need to get this job quickly because the Irish don't age well. And it's a theme I've been working a lot. I was going to say, holy cow. And I was like, and I was like, my face is acceptable for television now, but as Ted Kennedy is proof of my face is going to expand.

So I had this whole, and then what I remember most is then it's time to do it. It's really surreal. Jeff's over at the, you know, at the podium and we go, there's no band or anything. And I come out and I was immediately surprisingly comfortable.

I was just very, I like, I had always liked being on stage. And this felt, I was very comfortable doing the monologue, and then I slid over, and the minute I got behind the desk, I was just kind of happy. Mm-hmm. And so Mimi Rogers came out first,

and then Jason Alexander was second. I don't know if you remember this, but in between the two, it was like a commercial break, like a fake commercial break. What happened? It was a script packet. I guess it was the research or something. I don't know if you remember this. I wrote on the, and I just scribbled on the back, you're killing. And I slid it in front of him.

And what he did was he... It's called producing people. Do you still have that that's long no we shredded everything immediately right right right jeff wanted we were like the german we were like the germans as the russians came we were just shredding and burning everything um but yes i remember that very clearly and what i remember is the monologue went well and i just felt comfortable doing it it was very me yeah i wasn't trying to like tell jokes about Clinton or tell, I was just. And you're doing great icebreaking for that audience to like.

Yeah. To get to know you. You knew that they didn't know who you were. Well, also to let them overcome the shock of this is a very pale man wearing a white linen jacket with radiator stains on the back. But then I cross over and I talked to Mimi Rogers. That went well. And what I remember was there was a moment, which if you look at late night moments since,

or whatever, you'd think, well, this isn't that, it was fine. Right. But what happened was you got to see kind of for a second, I think a Conan-y, I was my very myself. Right. So Mimi Rogers is talking and I'm interviewing her. My posture's terrible. My hair's all droopy.

I'm wearing this awful jacket and I'm listening to her. And's terrible. My hair's all droopy. I'm wearing this awful jacket and I'm listening to her. And then she said, yeah, you know, people, I model. And she said, and a lot of people say modeling's easy, but it's a tough job. And I was being polite and agreeing, going, yeah, yeah, yeah. No, I can see, I can see. And then I just stopped myself and I go, wait a minute.

No, no, I'm sorry. I'm sorry. A tough job is like turning a big crank. And I mind turning a big crank. That A tough job is like turning a big crank. And I mind turning a big crank. That's a tough job, turning a big crank. And people laughed and it was very spontaneous. And the Jason Alexander went well, but that was a moment of me just interrupting

and then almost acting out a cartoon image. Physical comedy, yeah. And inserting my personality into the situation. And then it ended and I went with then it ended. And I went with, I think Lisa and I went to, man, I wish I could. Back to Fred Siegel. Yeah, back to Fred Siegel.

To sue them. Return the jacket. To sue them. And we put the jacket back on the shelf. I don't know how that stain got there. And I said, yeah. It came like that. I can't wear this.

There were cell phones then. Because I remember driving away. They were huge. A car phone yeah and i was in the car and lauren calls me and says that went well and i went yeah because he was watching in new york and he goes but it's going to be shandling yeah all right so right away now this is which i kind of knew yeah so that they were talking so i had done this thing and this thing i have to say the audition made me really want to do it. Cause I thought I was like a duck that had never been put in water.

And suddenly I was like, Oh, that felt right. And I'm not used to feeling good about anything. And it'll only go well. Yeah, exactly. It'll only go that well.

But you had a total flip where you're like, now I want, well, I was excited, but I couldn't even let myself think that. Yeah. So I was excited, but I couldn't get myself to that point yet.

But I remember we went out to Cape Mantolini. Remember Cape Mantolini, that restaurant that's on Wilshire? I went there with Lisa and everyone was really excited. And then I was 29 at the time. And my 30th birthday was about a week and a half away. I remember that. Yeah. Wow.

So then when my 30th, I'd go back to the Simpsons and it was just, well, get back to work. Yeah. And then I had a conversation a couple of days later, Lauren called me and I was in my car. So you're right. There were giant car phones, but you know, I was in my car and Lauren called me. He loves to break bad news on over a phone in a car. And he told me you were great yeah and he said i'll never forget he said bob wright loved your interview and he loved the whole crank thing when you did the crank thing he loved that and i remember thinking who the fuck is bob wright i don't know who bob wright is i didn't know who bob wright was and i said well and he said bob wright loves it and suzanne really loves it and i said well who are they and he, and Lauren was like, what are you talking about? He's the president of- He ran the network.

He ran the network of NBC and he and his wife, they, they expressed them this videotape out in Connecticut and they watched it and they're like, we like this weird Irish kid with the funny name. And that crank thing, man, that really cracked us up. I'm like, wow. They're still talking. Yeah, and so, but then he called me later on and said,

you know, the same thing that he had told Jeff. He said, look, it's not going to be you. You're not going to get 1230, but you did yourself a lot of good and they're probably going to give you like 130. And I remember thinking,

well, that would be great because there's no pressure. Right. If I got 130, there's no pressure. And wait a minute, that's cool.

And I'll never forget. Then you started wanting that. Yeah. Yeah. I still want 130. I take that now. No And I'll never forget. Then you started wanting that. Yeah, yeah. I still want 130. I take that now. No, I don't give it to you. But I hung up the phone and I was with Lisa and Lisa was like, well, that's, you know,

so you're not going to get 1230. And I said, I don't know if, I don't think the shedding is going to happen. And she said, well, Lauren just told you what's going to happen. And I said, I don't know why, but I just said, it doesn't make sense to me. Gary is a peer of Dave's

and he's killing it with his own show, Larry Sanders. And he's getting all of this critical acclaim and awards for making fun of the form. Who wants to go in every day and try and do it? And I said, it's not going to be Shanling. I don't think Shanling is going to do it. I think it doesn't make any sense to me he's too cautious he's too smart he's not gonna now he's not going to want to go in every day and figure this out and sure enough that's what ended up

happening yeah i think i told the story but i was i was out for lunch or something i had an office of broadway video in new york and i come back and i had all these messages when they used to be like paper messages that you would, you know. Yeah. And they were all people that had something to do with it. It was just obvious. I was like, right. Holy shit.

He got it. Oh, wow. And how long? It was just a couple of weeks after. What was it? Well, I remember one of the last things I remember from the old life, the black and white, the black and white portion of Wizard of Oz. Before I opened the cabin door, what I remember really well is I had a birthday party when I turned 30 and I had it at my apartment on Weatherly.

Apartment on the second floor was a sort of a duplex old 1920s place. And all my friends at the Simpsons and my writer friends came over and everyone brought gag gifts. Like someone brought me, Arsenio's like had written a book, like his, you know. So they all knew that you were in this process. That was no gag.

Yeah, everyone knew that I was in this process and everyone was talking about it, but it was kind of funny. Yeah, yeah. Oh yeah, you know, well, here's your how-to book by Arsenio. Yeah, yeah, for dummies. And Jeff was there

and we had this nice birthday party, which was April 18th, 1993. And then it was like, see ya. It was like, see ya, I'm going back to New York. Yeah, Jeff's going back to New York and I'm get on with my life. And it's in the back of my mind that something might happen, but I don't know what. And I want to say it's maybe I could look up the exact date, but it may have been a week later. I'm in a record at the Simpsons. It was in the basement in the building on the Fox lot.

And the way you do a record is there's a table read first. So the whole cast is there and we go through the script and then it's done and everyone applauds. And then what happens is we quickly talk about what changes may need to be made before they start doing the record. And the writers are all going to work that out, make these changes as they're recording to try and tighten it up just a little more. And I remember we had just finished and we're starting to talk about it when there's a phone call. And someone in the room said, Conan, the phone's for you. And I picked it up and I put the phone to my ear and it's Gavin Pallone, who's still my manager. I've been with him forever. He said, you got 1230.

And I don't know why, but I went, and I said this not in a celebratory way, I said it in a defeated way. He said, you got 1230. And I went, I know. Because I just had this. You had a premonition. I just knew for some fucking reason.

You knew it wasn't over. Especially once you didn't want it. I hung up the phone. Yeah, I hung up the phone and I start to quietly walk out of the room. I didn't say anything to anybody. Leave the room. I go, I walk up the stairs.

I walk outside. And I was told by Gavin, I said, I know. And then he said, Don Ulmer's calling you in like five minutes in your office. And I hung up and I start walking. And then I start going into a slight, it's very cinematic, but I started walking fast. Then I start running and I run to my office.

And then he's saying, okay, here's the plan. You got it kid. I think it's all crazy, but you got it. Now here's the idea. He said, you're going on the Tonight Show tonight because I'm sick of us getting scooped. What? They've scooped us the whole time.

We're going to flip the script on the media. He had this very combative, sporty kind of, so he said, Jay's going to just say, we got the new host for the late night show. Here he is and you're going to walk out there and you're just going to, and he said, kick it in the balls, balls you know and really show him who's who and i'm just the kid that just came out of a record yeah and i'm like um who he's like shut up get in your car

and get over to nbc right now before the press finds out so the next thing i know i'm driving over to and i'm in a total oh no panic and then sure enough, Jay calls me out. And I remembered Robert. And I think this is good. Robert was like, don't take any big swings. Right. You know, because the worst thing that I could do. Michelle in the background is going, I was kidding.

Yeah, yeah. She was like, you have a lot to lose. The Simpsons is a good gig. Yeah. So what Robert said? I just basically went out there and went you know yeah it's real you know and jay was like well you know good luck to you and then whatever and played it straight i just played it straight like i and i remembered uh people were like well if

that's the new host of late night and i was like you know he didn't come out and kill and i think oh my i really wanted me to go out there and say like all right everybody now listen to this you know and you're that's do the great thing again yeah well jeff we're so you that i was out there and say like, all right, everybody, now listen to this, you know, and that's incredibly smart. Yeah. Well, Jeff, so you, that night, I was not there.

I was in New York. You were back in New York. I was in New York, yeah. And did you tune in? I had to start producing. I did. Did you guys talk before you went on?

I don't think, we probably, I don't think so. Okay, all right. I'm not sure we did it. I don't remember. All right. So then what happened

next with you two? We had to figure out how to make a show. And Conan came back to New York, got a place. I had to, well, the crazy thing is I had to go, they wanted to introduce me

to the press in the Rainbow Room. Yeah, yeah. That was the first big hurdle was I had to immediately come east. It was not clear because then NBC started to get into it with Fox and Fox was like, excuse me, he's under contract. I can't believe it. And we were like, well, this one in a billion year accident just happened where one of your writers is going to get to. And it wasn't again, I want to be clear. It was not the Simpsons.

The Simpsons were really great about it, but there was an executive at Fox who was saying, no, I don't. So NBC and I, I think, I think I had to pay money. I had to pay money and NBC had to pay money to get me out of my Simpsons

contract. That's crazy because at the time these shows were making so much money and they were nickel and diming every little thing you could even think of. That's how they made it. It was the same extra below. No, but- You had a line at the press conference.

Yes. What was it? The press conference had very much the feel of, we all met, it was going to be in the Rainbow Room, which is the top of Rockforce Center. And everyone from the press corps was going to be there. And I was going to go out and meet the press. And we all met at Lauren's apartment and the NBC people were there.

And then we walked through the park. It is now early May. We're walking through the park and I'm seeing Rockforce Center get closer and closer and closer. And I know that I have to go to the top of this tower and then meet the nastiest press in the history of media this is cinematic as well yeah and so we're walking there and then as we are getting to 30 rock trying to keep it light and trying to stay loose a reporter comes up to me he says i forget if he said he was from the post or newsweek but he said hey conan my job is i was at letterman's letterman had had a press conference for his new

cbs show at radio city like the week before and of course being you know he killed destroyed right And my job is, I was at Letterman's, Letterman had a press conference for his new CBS show at Radio City like the week before. And of course being, you know, he killed, destroyed. He said, I was at Letterman's press conference last week and I know how many laughs he got on my job is to count how many laughs you get and see how you stack up. And he told me that as we were going through the, on the north side.

That should be illegal. Right in between Radio City and Rockford Center. We were going in right there and he was like, my job's to count how many laughs. So it was literally like good luck Spartacus in the ring. So I go up there, Lauren talks briefly, and then they, and there's a shot. I mean, Vanity Fair covered it at the time.

And there's a great, the iconic photographer. Annie Lewis. Annie Lewis took a shot of me, a reverse shot. I'm in the front and it's the entire press corps and explosion of photographs. Oh, wow. And I'm, as I said, I'm a week and a half earlier. I was in the room at the Simpsons. It's still not real. No, but I remember that the thing that saved my ass was I get up

to the microphone. I know, now I remember. And Stuttering John from the Howard Stern show is there, and he's wearing a terrible he's wearing a fake mustache and fake glasses and like a wig. And so he goes like, Conan, Conan! He said, who'd you have to sleep with to get this job? And I just

said, no one I wasn't sleeping with before. Next question. And everybody laughed. And then I just, just said, uh, no one I wasn't sleeping with before. Next question. And everybody laughed. And then I was like, Hey, Hey, that's stuttering. John, John, take off the wig. Cause he kept, his job was to fuck with me. Yeah. And I was, I was loving it. And, and I was, anytime he'd say something, I'd be like, I would have fun with it. And then I was like, John, come on, take off the, and it ended up. Is it, wasn't there a, somebody said to you something about being a relative unknown? Yeah. He said, sir, aren't you a relative unknown?

How is it? Yeah, aren't you a relative unknown? I said, sir, I am a complete unknown. And then people were like... That's great. That's what I was thinking of. Foolishly, the press conference went really well. And the take was, well, he's funny and it could work.

That's all you wanted. He got three laughs. He got three laughs. He got three laughs. I'm dying to hear that. I want to dig up that article. But you did a thing that you've done every time since I think where you have an event is like if you can find one person. Yes. As a through line and to play off of.

And you've always been great at. I always try and find who's going to be my foil. Right. And then use them as the through line. And Stuttering John was there, and he was my foil. And to make things even crazier, that event's over, and the first thing I hear is Bob Wright of We Love the Crank. Do the crank thing. Bob Wright's having a 50th birthday party in Connecticut, and they want you to go up and be one of the people who speaks. Oh my God.

It doesn't stop. No, one of the people who speaks. And it's in three days. And I said, okay. So I come up with an idea for what I could do. And I worked on it with Robert. I get in a town car with Lorne, because he's coming too. And we drive out to this nice part of

Connecticut, and we walk into this very fancy country club where there's a big party, and I recognize all these famous people. You know, there's all these people from the Today Show, and all these people from all the different NBC shows are there to salute Bob Bright on his 50th, and my job is to get up and speak,

and I get there, and who's standing ramrod straight in the corner but and speak. And I get there and who's standing ramrod straight in the corner, but Johnny Carson. Oh, God. And I am the opener. This guy can't catch a break. I am the opener for Johnny Carson. And my previous experience is I did some pretty good improv at the Groundlings and thought of one good quip with Mimi Rogers. And so he's standing there

and he's wearing sunglasses inside, remember? And he just looked, it's Johnny Carson. It's the biggest thing. And suddenly I'm being introduced to him. And I said, well, I called him Mr. Carson. And he went, please call me Johnny. And I went, oh, Johnny. And he was very, he seemed kind of quiet and reserved.

So I didn't say that much to him. And then I got up and I think the idea that I went with was giving a toast about someone I clearly don't know. So it was like, what can I tell you about,

you know, Bob Wright? And it was, all the jokes were things like, he's, I think, 5'9". He is the, and it's clear, I've just looked stuff up on Wikipedia,

which actually didn't exist then. Didn't exist. Had that experience. And then he like applauded and gave like a little like good for you kind of. Yeah. That was okay. It was fine. And.

It was no crank. Yeah, it was no crank. And he said, follow that Carson. Yeah. I should have totally, I should have totally been like, and now fucking Johnny Carson. Let's see it. But then he got up and of course, blew the lid off the place.

But that was how rapidly insane things were happening. You know, it was like Rainbow Room, meet the New York press and be confronted by Stuttering John. Off to open for Johnny Carson.

And it was just this cavalcade of craziness. I remember, and then it was go meet all the affiliates. I had to go like around the United States and meet affiliates. That seems least like that's no fun it's like a cool down period compared to what you just described the one point i would make that i'm still blown away by is

that this process of bullshittery that had to happen of press and affiliates and birthday parties. And by the time that's over, it's late May, early June. And our start date was September 13th. Yeah. No band, no writers. It's myself and Jeff, no bookers, no set. They've completely taken out the Letterman set. And so there's just a 6A is just an empty concrete rectangle. And that's the part that never makes sense to me is how quickly, you know, today when I hear about someone doing a show, it's like, well, you'll see it in six months, you'll see it in a year. And I've got to figure the idea that they found the person with the least experience yeah in the history of the medium and said you can really get started on june 1st right i wasn't exactly i wasn't exactly experienced at doing a late night

talk show i'd done a lot of a lot of different types of shows. And kids in the hall, but that's a totally different pre-taped. There is nothing, well, there were only two or three shows of that kind of time. So, you know, I had no experience. So you were both learning. Yeah, it was crazy.

So who did you turn to for advice? I didn't really have. He's probably pretty busy. No, a little bit of Lauren. Lauren, there was a lot of, we had a lot of Saturday Night Live people helping us and different variations of helping

and not helping. I don't know if they were trying to kill us or what, but that's a whole other episode. You realize this is nine podcasts. Yes. We haven't even gotten to 1993. I knew And we sort of realized that we had to. Haven't even gotten to 1993. I knew a lot of those people because I had worked with them before. And we sort of managed our way through that.

And the process of getting a band was insane. The process of getting a cell built was insane. There is a story, a crazy story behind everything. And moments of true despair to the point of there were, I think, maybe seven different times just in that summer where I fantasized, no joke, about getting hurt. I didn't want to die. But I remembered very clearly thinking if I was hit by a car, it was very clear to me that it can't be my fault. But if something were to happen to me and I'd be badly injured, I'd be off the hook. And that might be a good way. And so I would also want an induced coma. I would just want to check out. It was generous. It was Robert Morton at the

time was producing the Letterman show. He was generous. He was a friend of mine. You were already friends. Yeah, but he was generous about it. And was there an early moment you two remember being thrown into this where there was like things you bonded over in particular? We've never bonded. Eight minutes ago. We wanted a hug.

Eight minutes ago, I really started to think, this Jeff Ross guy, there's something to him. My whole thing was just try to make it as easy as possible for Conan. Right. Just try to keep him away from all the bullshit. At that time, it was kind of impossible because there were a lot of opposing forces. Right. And people who were less than helpful when they were made like they were being helpful.

It was just a lot of craziness going on. And like passive aggressive, I'm sure. Yeah, a lot of craziness. And I think the, and this is where I really have to, I think I've tried to say this a lot in my career and on my last TBS show, but it can't be said enough.

The two big things that had to happen were initiated and made possible by Lorne. So first of all, there's this weird opening in the universe. I always make fun of Marvel movies because I hate a portal that opens in the sky. I always think it's a portal opened and lazy, lazy writing came in another dimension. And so, but this weird portal opened in the sky where there was a second where this big TV job was kind of in play. And Lorne, for whatever reason, and I still maintain he may have fucked up, said Conan O'Brien. Now, that's huge because Lorne was the only person in show business who had that power,

one of the only people. And he's also clearly saw something and said, I think he could do it. Probably regretted it almost immediately. And I've actually told this to, when I went back to SNL a couple of months ago, I said, I'm sure you regretted that immediately. And he was like, no, but I could tell like, but in fairness to Lauren, he did that.

And then the second thing he did was he said, Jeff Ross. And my dad over the years, who likes to ask a question more than once, the same question, but over the years go like, now, how did Jeff get into the equation? And I would always say, well, Lauren was the one who brought Jeff in. And he would go like, well, Jeff is very key. And I go, yes, Jeff's the key. And then I'd count a year and a half. He'd be like, now tell me how did Jeff,

that's important because Jeff is very, he seems to compliment your energy. Yes, that's right, Dad. We've talked about this several times. Yeah, yeah, yeah, sure. Is Lisa Kudrow still buying your clothes? Whatever happened to Lisa Kudrow? Well, a year later, she gets,

I'm not done with my question. Anyway, but Lauren, by just moving his pinky, he says, well, it's Conan O'Brien, it's Jeff Ross. And I do think those are two massive key moves. And then the third move that needed to happen at the beginning was Robert Smigel.

And I pushed for that. And of course, I only knew Robert because of SNL, where I worked with him for all these years. And I knew that he had the sensibility. Like we used to talk about this. We used to talk about comedy. And I knew that robert kind of had to be there and lauren you know i think was reluctant to lose robert from snl and that was a whole story but when you think about it the three main players that needed to happen

for everything else to happen really come through right at the top and snl and they happen fairly quickly and then the rest is i always think it's one of those movies like you start with robin hood and he's walking through the forest and then you know he starts fighting with someone on a stream and it's it's fryer tuck you're with me and then you pick up people as you go i i think of it as jeff and i pretty much start the journey out together and Robert's there almost immediately. Then it's the three of us. And then it's this whole odyssey of, you know,

literally Jeff Garland saying, Hey, check out this guy, Andy Richter. And we do. And I have lunch with him and meet him at a, at a deli, as I've said many times.

And he came in and I immediately, I mean, a lot of it's instinctual, but immediately I was like, this guy needs to be part of this adventure because he's fantastic. You were like Lauren all of a sudden. You were just like, ah, this guy. The stuff that's fascinating to me is how do you,

those initial elements are the fascinating part. And then everything else is a good story. And you guys have done a great job of mining these incredible stories because we put together, because it happened so quickly and so strangely, we put together a group of people that didn't know anything about TV and really didn't have experience. And then we ended up, you know, we inherited our crew from Letterman's old show. And he did, Dave did a very different kind of show. And suddenly we're telling 62-year-old cameramen

who've never had to move, we've got a funny idea where Conan races down 6th Avenue and you follow him. And they were like, how about you go fuck yourself?

There's a lot of that. I'll be on a break. Yeah. And once you hit September 13th when we premiere 93, the next two years

is us. Year and a half. Two and a half. No, no, year and a half two and a half no no year and a half too no i think it was over two years of we're in terrible terrible danger of being canceled in a second we were canceled at one point but also justified fear because yeah there was we were i mean you've said it was week to week for a while. It was just day to day. All we did was, this is the way I felt, is I had like visors on. I was like one of those horses. Right. You know what I mean? You still are very, you're still very horse like.

Thank you very much. I appreciate that. We gave Jeff a sugar cube after every anecdote. I could use one now. This goes much longer. Oh my God. Jeff, we haven't even gotten to your side. But you know what I'm saying? We're going to go back and retell the whole story through but you realize that this is you just have to put your head down and not pay attention to a lot of things just go forward i mean i think

it's just i still to this day cannot believe that somehow we got away with it 100 and you know one thing i wanted to say, I had one of the surreal moments just pop into my head and one of them was, we move in and we take over these offices. They were offices

that had been like an insurance company or something. But they ended up being our late night offices for all those 16 years. And we move in and there's nobody yet.

I mean, literally there's myself and Jeff. We had offices on the office. Remember the office at Corners? Jeff. And there's no, there's nobody yet. I mean, literally there's myself and Jeff. We had offices on the office. Remember the, yeah, the office and corners? Jeff, Jeff. And there was nobody else there. So you were literally a hundred feet apart.

We had two corners. At least, at least a hundred feet apart. But Jeff, Jeff had the offices that looked at the, at the sign for Radio City on the north side. And I had the south side. I was down like where the writers are and Jeff was upwards. You know, all the adults who make the show really work are up on that side. And I was with like where the writers are and Jeff was upwards. You know, all the adults who make the show really work

are up on that side. And I was with the idiots. And, but at the time, there's no one's there yet. People were in the press of hiring people. So you could look it up, but Dave winds up his last late night show, probably sometime in June, I'm guessing.

And where am I? I'm on the ninth floor in my office and I'm watching the feed and I'm watching Dave record his last show. Just three floors below you. Three floors below me. And he's recording it in the studio that I'm going to take over, but we haven't even gotten started yet. And I'm sitting there watching it. And so Dave does this amazing show, last show. And then Bruce Springsteen comes out and does Glory Days. Right. And I'm in my office watching this and then it ends and Dave does his final words and he says,

I'm moving on, this has been a really, and he says, the last thing he says is, and Conan O'Brien, I don't know much about the man, but I believe he shot somebody once, you know, which it would always get old. Sure. And then he said, I hope someday he has me on his show.

That'd be nice. Anyway, good night. That ends. And I'm like, for the first time, as long as Dave was on the air, I felt this isn't real. It's down the road. And once he left,

suddenly it's like, you're up, kid. Oh, wait. DiMaggio just left the batter's box. He just hit a home run. Yeah. You're up. I hope you're warm. Oh, here I kid. Oh, wait. Right. DiMaggio just left the batter's box. He just hit a home run. Yeah. You're up. Yeah, hope you're warm. Oh, here I am.

Also, we went down. This bat feels heavy. We went down there after the show. I was going to get to that, yeah. And what was surreal to me, first of all, they're all there. Who's they? Joe just sprung all the executives. They were all diverse.

No, no, no. But it's like, Letterman's just done his last show, so there's a whole thing. Bruce is in the hall wearing like a flannel shirt and having a, you know, a bottle of, literally like a,

he had like a beer bottle because someone had put beer out. It's a prop. And yeah, it was just filled with La Croix. It had La Croix water in it. Part of his look. Give me my La Croix.

That looks like beer. So Dave was in this little tiny dressing room and someone said, you should go in there. Suddenly I'm in a tiny, tiny room with David Letterman who's just done his last show. And he wishes me well. And I said, well, that was really amazing. And well, I should go and start making the show

that will replace your iconic show, I suppose. And I walk outside and Tom Hanks was a guest on the last show. And Tom Hanks is there with his wife, Rita. And Tom looks at me and I knew him from being a writer on SNL. And he used to call Robert, Bob Odenkirk and I, and Greg Daniels, the boiler room boys.

He'd be like, hey fellas, we're the boiler room fellas. Get over here, fellas. And so he was like, he looked at me and he stared right through me and like put his hands on my shoulders and he said what's just happened to you doesn't happen wow it never happens and i don't know exactly how to take that but i don't think he meant anything, but he was pretty much saying, this is kind of unprecedented in show business history. Okay, I gotta go now. Oh, no.

Don't fuck this up. I also remember being- That I remember very clearly. I also remember being in that hallway and immediately they were ripping the set out. Oh, my God. And I was just watching them rip the set out. And shitting on the floor.

Pretty much. And just going, our them rip this set out. And shitting on the floor. Pretty much. And just going, and our set experience had little to be desired, you know, with that first set. And we're going through all that. I'm watching the set being ripped out. I'm just like, oh, my God. Wow. Oh, that's real. We just got to figure it out.

So it was empty by probably the next two days later. Yeah. I think that night. There's a thing you hear about a lot back before people, there were rules and laws about childcare that if you wanted to teach a child to swim, you would just take the child

and throw him into the deep end of the pool. This was like, I'm taking the child into a C-47 plane and throwing them out into the Arctic waters. And the worst thing about it all was like, I think if it had been done to me, my psychological response would have been, you know, if I was told by the government,

your name has been selected randomly and you have to replace Letterman and this is your, your job to save America. I would have had a very different attitude about it, but in my own fucked up Catholic way, I think I was very much, you asked for this, asshole. And so I- You got what you wanted. I had, yeah, you got what you wanted, fucker.

Now let's see, you know, you put yourself in this position. You said yes, because someone just had to host a talk show. And the voice in my head is far more punitive than anything anyone can ever say to me. And so I just beat the shit out of myself all the time. And I now think that the crazy thing about when I look at the audition or the times I've seen it since, I was more relaxed in the audition than I was on television.

Because psychologically, well, I'm being asked to try out. I'll do my part. Nothing to lose. nothing to lose nothing to lose and then the minute it's i took it very seriously yes and um it just took me a while for the volume it was literally the volume and the amount of work we were doing and the volume of shows and it's getting malcolmwell's 10,000 hours, the hard way in front of everybody. In front of it. In front of everybody.

That's the craziest part of it to me. And so you could probably see, watch, some program could probably take one image, three images a show from every show the first two years and speed them up, and you would literally see somebody, my skeletal structure would change from the sheer, I wanted it to work. I was, I was not going to not work. I was thinking it was, this is going to work because it has to work because being a joke trivia question is not an

option. Right. Yeah. But, but that to me, just learning to do that on the job, because you mentioned like Tina Fey and, you know, Seth, like, yes, they were writer background, but then they had all this performance experience kind of under the radar. At Second City. Yeah. Almost everyone in television started, you know, Letterman was a weatherman and even that. Yeah. Just that. Yeah. It's just that little practice. Just me in front of a camera. Right. To be fair, I used to go to department stores a lot that were selling televisions.

And they used to have a video camera. And I would do the thing where I, I swear to God, I had spent a lot of time. I take it back. Really gotten my chops. But it was. Flo of time. Yeah. I had really gotten my chops. But it was. Floor five. Yeah. It is a very improbable story.

And what's crazy to me is that's the beginning. Yeah. And we've told you one twentieth of the good stuff because there's so much insanity that happened. And we're saving that for the book um but that's just the beginning yeah and you could believe like and then finally the ship righted itself and went off to have a pleasant career we haven't gotten to the tonight show like yeah that is in every way as insane and unprecedented and crazy and counterintuitive as the beginning yes and that happens 16 years later yeah what i was going to say was isn't that crazy what's fascinating is we

told this part of the story and then i go i was about to say well and then we went up those elevators in the coolest building to that you could do television in in the world for the next 16 years yeah it's crazy yeah yeah the volume of stuff and the of the variety of things that we tried yeah i can't even i see it now and i have no connection to it so i mean we used to do a piece where we would do a whole like soap opera in front of the audience and with famous people john lithgow did it john lithgow did it and martin sheen did it and we would have people in the audience wear a green like sock a green screen green screen over their head so that we could drop them in and put their heads on the bodies of actors who were there so that the audience would have a lot, an audience member who just showed up.

Yeah. Paula's looking at me horrified. He had no recollection. Yeah, Paula Davis is here. Stay in your seat. That's one of the early hires. It was called, Paula Davis,

one of the first people we hired to be our booker. And she's sitting here and Paula, you don't even remember this. You booked it. You booked, you booked.

She didn't know you hosted. Yeah. I'm Conan, by the way. She's like, know you hosted yeah she I'm Conan by the way um um she's like where's Corden I'm like okay we'll get to that

but uh his American accent is impressive there are maybe 75 to 100 sketches or more right

that someone could tell me we did right and I would say you won't believe that don't do that how would that even work and

stay in your seat theater it was called so that it was putting out a newspaper every day and there was no you could never

not move the clock back and then in the middle of that somebody says let's do the show on the circle line right okay

yeah let's get a circle line right a circle line boat yeah the boats that go around manhattan yeah but i mean that's i have to say robert gets a lot of credit for robert has large eyes like there's that old saying my grandmother used to say if you didn't finish your food she'd say well your eyes were bigger than your stomach. Right. Yeah. And Robert has creatively huge eyes. Yes. Let's rent a Zeppelin.

Yes. Let's fill it with cheddar cheese. Let's get Paula to book. And he makes it happen. Yeah. And let's get Paula. He wills it. He wills it through an insane, you know, and things get crazy and hairy and there are fist fights and there's shouting.

And maybe people get killed during the sketch. Sure. Who knows? But the whole thing was, there was this, when we were really taking heat early on. Right. In,

through at 93 and people are, at the time there were reviews that said things like, it would be really nice if, you know, Conan died, you know, and it'd be great if Andy died with him. You know,

it just, just people were just very upset by it. And that was actually in print, I think, once. Your hometown paper. Yeah, yeah. Your father wrote it. Exactly, I was gonna say. Written by Dr. Thomas O'Brien.

If he died, it wouldn't be his fault. You see, he never adequately explained Jeff Ross to me. Yeah, I just need him. Now wouldn't be his fault. You see, he never adequately explained Jeff Ross to me. Now he must be punished. But there was a time when I think even Lorne was saying, couldn't you just interview people? And couldn't it be like, because our comedy was very aggressive and aggressively strange. And I think still looks that way. And they thought, well, this Conan guy, he cleans up nice and he's affable. Why can't he just be affable and chat with people?

And that way there's less sticky edges. Instead, you know, Conan's yodeling and he's wearing a bikini and Andy's dressed as a monkey. And there's a punk rock element to it. Like, like it or go fuck yourself. And, but, but one of the great things about that, when you wound up your show in TBS last year, we're all these successful,

like Seth Rogen and all these other big names who wouldn't, this wouldn't even occur to you at the time. You were just trying to do a show every night. Yeah. They all ate the feast of all this comedy you were making. Yeah, we're like, finally someone's making comedy for me, I think is how people felt. That must have been very satisfying. It was, but I have to say, I don't know how you felt, Jeff. the most is that you know haters and mulanies and all these these people who are so crazy talented

and good at what they do and brilliant and they say nice things about and and what our show meant to them back in the day and my immediate response is couldn't you have said anything because because nothing was old enough to write yeah like couldn't you why weren't you in nielsen house or o'brien in fairness to that, there were a couple of situations where somebody's kids, they were hearing, like, executives. I can't remember who it was. Who was it?

There was a guy who, and again, this is probably for another installment, but there was a guy who was sort of hired to kick us in the ass. And, you know, let's get this thing moving again. I mean, we got to figure this out and it was like an episode of a sitcom

where a character comes in and Joel Sargent moves in with the family and boy, does he turn things upside down. But I remember him telling us,

you got to pull this together. You got to da, da, da. Then he went off to visit his, I believe it was his son who went to Boston College. So he went to visit his son and he was hanging out

in the dorm room and he's like, so guys, you know, tell me, what is everybody watching these days? What are the kids loving? And he said, the dorm room was like Conan. Wow. And he was saying, no, no, seriously, seriously, seriously, you know, do you guys like Jag? That shows on its way out. Do you guys like Carolina City? Right. And they were like, no, no, it's, it's, it's, we watch Conan. It's so great and weird. And to his credit, he did repeat that.

He told me, he didn't have to tell me, but he told me. Well, he was going to take credit for it. I mean, in the end, that's probably the kind of thing that saved us. Yes. Yes. I mean, the first thing that saved us was nobody was paying attention. We could just do whatever we wanted. Right.

Yeah. And then it became. After the initial russian i think what helped save us is that we were in new york yeah and had we been in los angeles where they could come in you know if if we had been in los angeles they could have been there every day and they would have seen me putting on an octopus costume right and us putting a green felt sock over martin sheen's head Right. And they would have said, stop. We just saw that on the feed.

Stop. Have Dick Cavett on and interview him and be pleasant to you, motherfucker. And instead, and also I think there was a, we were a car accident. People stayed away from us for a while because no one wanted to own it. And we have to give a shout out to someone

who was a real stalwart, Rick Ludwin, who is no longer with us. Rick Ludwin was the NBC executive in charge of Late Night. And he was horrified by a lot that we were doing early on. But he was there and he was watching audiences laugh at us. He was the first executive to get it. Yes. Yeah. And had the only one with the balls to go into a room and go, it's good. Yeah. He said something. I don't get it. He said something's happening here. You know, there's something happening here. What it is ain't exactly clear.

You can edit that out or actually put music to it. We'll loop it. There's a man with a gun over there. Conan's cover. Telling me I've got to beware. It's time to stop. Don't make that show. Everybody says my favorite Stoogesmo.

Anyway. This is why I really. You get topical. You know what? If I had said. If Weird Al hadn't come along. If I had sung that ditty at my rehearsal, you wouldn't know me now.

I'd be at the guy at Ikea. I know. There was a divine force helping you through it. Helping me not make stupid songs up. But yeah, Rick Ludwin said, there's something happening there. And he just doubled down and went to bat for us and remained a good friend of us all through, you know, everything.

And even through the Tonight Show craziness was like, nope, disagreed with people audibly and got fired. Well, yeah, we have to wrap this up. We do have to wrap this up. So everyone can just look up the Tonight Show and the serious deal.

People can read about that online. Well, this will be a new spinoff series. This was cathartic. Couldn't run 20 seasons. This is amazing. It's tough. And I know I run off at the mouth, but it's very, I'm very, I don't talk about this stuff a lot. And so when it comes up in this forum, you realize it's like PTSD.

Right. You start talking and it's hard to stop. No, no. It just felt very visceral. Like you were there and you were remembering the Lucite table and it was nice seeing all those details. But it's also easier to talk to you guys about it because you know what it is.

Right. Yeah. But also the process of talking about it, it's almost like to reaffirm that it really happened. Yeah. Well, that's why I will say I'm grateful to you guys for doing this podcast because as much as I,

I have trouble listening to. To our voices. To our podcast. Well, it's just the lack of chemistry. Let's get a robot. What else? And a bar of soap. We'll have you know.

No, no, no. I hope I'm the soap. Oh, you are definitely the soap. I'll have you know. No, no, no. I hope I'm the soap. Oh, you are definitely the soap. I love being a robot. But bleep, bleep. Man, where's my oil? You know the joint. No, I have trouble.

I have trouble going back. I have trouble going back there sometimes. You know what I mean? I have trouble going back. But the fact that you guys are talking to robert and bill toll and you are you are i mean when i heard that you guys had done a deep dive on the old-timey baseball remote and found nell yes she hasn't forgotten and and found her and and that is a magical moment in my life and this is very name droppy but we just paul and i went and saw uh jack white do his show recently

and he was telling me afterwards we both realized we're going to be in the seattle area around the This is very name-droppy, but we just, Paul and I went and saw Jack White do his show recently. And he was telling me afterwards, we both realized we're going to be in the Seattle area around the same time. And he said, oh, I'm playing a baseball game then with a bunch of friends. And I'm going to be in there because he's on tour. And he said, you should stop by. You could play with us. And he said, and you could do it as an old-timey guy. And then he's like quoting from it.

And I'm realizing he probably saw that when he was like eight, you know. Why didn't he write a letter? Exactly. That's what got him into comedy. I'm really grateful that you guys are doing this because, you know, you can love us, you can hate us, but whatever happened during this crazy 28, 29-year span was authentic, kooky, and involved a lot of brilliant, weird, difficult, lovable people, youvable people in this movable feast that just seems to, I mean, now it's continuing in audio form and I think will morph into other things.

But I just love that you guys are getting these stories down because none of us should have ever been allowed to be in Rock Far Center or Warner Brothers or any of these places. It's insane. And I love that you're getting this sort of oral history of a terrible mistake. Right, right, right. Well, people love talking about it, too.

I mean, it's easy to get. And same, once the juices start flowing, everyone's fond memories. And you've meant a lot to so many people. Yeah, there's a lot of stories adjacent to your story that you might not want to know about. Yeah, I don't want to know. Speaking of Bill Tall and props. I don't want to know

what prison Bill was in. That's who comes to mind. Just Bill. Bill Tall was being led to the execution chamber when he heard on the radio. They made me build the chamber. A final appeal.

He heard on the radio that Conan was the new host of Late Night, and he was like, that sounds good. And he wriggled free and got out a window. Well, thank you. Yeah. Thank you both. Stop by anytime.

Anytime. Yes. Thank you very much. This was great, guys. Thank you. That was mostly Conan and some Jeff Ross. Yeah. And a little bit of us.

Oh, yeah. Yeah, yeah. We're sprinkled. We were there. It's such an amazing story. It is. I know. I really don't get tired of it.

I mean that. No. And there's new details always emerging as well. You know, it was amazing to me hearing all of that. I think I've heard some of those stories separately, like little parts of it. And to hear it compressed like that, where he just went from one test to the next test to the next. Yeah. Oh, so stressful.

Oh, my. It's just imagining. It's just unbelievable. It's like a nightmare. And there was no let up it was just like it was literally like going down a water slide that just never stopped and it's just like with knives yeah yes yeah no water it is an amazing uh showbiz story so i'm it is i can't wait for the made for tv movie about it on Hallmark.

You know what? This season has been so fun for me. I've loved hearing and talking to all the people that have been a part of the show. It was great. Touched so many people in so many different ways and just everyone has such fond memories. There's so many people. There just isn't enough time. There's so many more people that I'd love to talk to and catch up with. But the people we had on were fantastic. The writers and the guests. So many writers.

Oh, my God. The Brian Rich story about when he applied for his own job and got it under an alias. Right. Because he was leaving the show. He reapplied to replace himself and got the job oh i know and then and then and then hired someone to play him as the quote new writer it was just a that is i'm so glad that story got to be told it's an epic story yeah and then all these other parts of it came out and and then we dug up nell who, who is also kind of famous in the Conan lore from his old timey baseball remote.

She's still doing her thing. She's still Nell-ing out. Yeah. She really is an enigma. Like, I don't. She was exact, seemed exactly the same. Mm-hmm. Yeah.

We talked to a former head of state, the former president of Finland. That's right. Agreed to speak to us. We didn't trick her into it she's on our 100th episode along with robert smigel who we discussed earlier i think people really loved our when we talked to bill tall and john rowe the prop masters yes oh there's so many animal corpse stories i know and but they also just talked about straight up about the bedlam of getting the show together from their point of view every day back in 30 Rock. And I just love that, you know, you think of 30 Rock as a state building and they were just running some crazy schemes out of that prop room.

They were cutting wires and moving pipes around, dissolving animals in acid. Right. All under extreme deadlines. Yes. For a good cause. Oh, and you know what show I'm watching? And I think it's because we got to interview her. I love that for you.

And I think that show's really funny. Oh, Vanessa Bayer's show? Vanessa Bayer, who we interviewed. Yes, who was a former Conan intern. Yeah, and she'd been a guest on the show etc etc and and i remember the time she's talking about the show she was working on and i was like yeah sure everyone's working on a show and it's it's on showtime it's it's really i really well done show oh that's great i love her if you haven't watched it there's such a lot of talent that came through the Conan halls. Yeah. From intern

to employee to guest. Yeah. It's been a really fun season. Yeah, it's been fun. I've loved seeing you every week and getting to chat. I know, that's my favorite part. It's my favorite part. Has been talking to you. That's been my favorite part, too. I'm not even... Sadly, the season is over.

It's been so much fun it's been a blast and uh i you know we'll keep in touch we'll keep yakking yeah we'll keep you posted on anything that's coming up and see where conan heads next you know in addition to the podcast what else he's got up his sleeve yeah that's right i I'm ready to dig into his trash and maybe get some clues. And if you like the show, you can support us by rating Inside Conan an important Hollywood podcast on iTunes and leave us

a review. Yeah, thanks for doing that. Yes. In advance. Exactly. Well, it's been a really fun season and you know, we couldn't have done it without our listeners. Because why, Sweeney? We love you. It's true.

Thanks for letting me say it this time. Inside Conan, an important Hollywood podcast, is hosted by Mike Sweeney and me, Jessie Gaskell. Produced by Sean Doherty. Our production coordinator is Lisa Byrne. Executive produced by Joanna Solotaroff, 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. Give birth to a calf, it's Conan! This has been a Team Coco production.