Conan's 'Uphill Climb' To Late-Night Throne

Conan's 'Uphill Climb' To Late-Night Throne

1:57pm Aug 28, 2013
Conan O'Brien interviews Bruce Willis in a 2005 episode of Late Night With Conan O'Brien.
Conan O'Brien interviews Bruce Willis in a 2005 episode of <em>Late Night With Conan O'Brien.</em>
NBC / Getty Images

Conan O'Brien has probably had the most unusual career trajectory of any current late-night host. When he joined NBC's Late Night in 1993, replacing David Letterman, he had virtually no on-air experience. He did, however, have comedy-writing chops: O'Brien edited the humor magazine The Harvard Lampoon as a student, then wrote for Saturday Night Live and was a writer and producer for The Simpsons.

Although it took him a while to get comfortable in front of the camera — many critics initially gave him bad reviews — he eventually did so well on Late Night that he became the host of The Tonight Show in 2009, after Jay Leno's ill-fated move to prime time. But that arrangement was short-lived: Leno's show was canceled, the host moved back to Tonight, and O'Brien eventually landed at TBS in the 11 p.m. slot.

O'Brien spoke with Fresh Air's Terry Gross in 2003, a few days before a special broadcast celebrating his 10th anniversary at Late Night.

Interview Highlights

On taking over for Letterman

"I always knew that this was going to be hard. I always knew that it was going to be an uphill climb to replace Letterman from complete obscurity with no experience, but I think I had to go through it to know exactly what a titanic effort that was going to be. So when I look at that guy [himself in 1993], I kind of feel sorry for him. But at the same time, I think it's nice because I look at him now and say, 'Don't worry, it's all going to work out.' "

On his self-proclaimed Irish-Catholic repression

"This is turning into a therapy session. I'm going to get a bill from NPR. The repression is all there. It's real. It fuels the depression and the self-hate. It's like a Rube Goldberg device: The depression drops down onto the self-hate, which triggers the self-loathing, which then fuels the anger, which curdles into comedy, and then it sadly leads to a slow, quiet drinking problem.

"It all fits. It's like a Swiss watch the way it interrelates. ... There's an element of truth to everything I say and then I exaggerate."

On improvisational comedy in talk shows

"You're just playing a game, in a way, turning the audience into a foil, and we're just going back and forth. I think the best thing I ever did was, years before I got the Late Night show, when I first got out to Los Angeles to be a television writer, the first thing I did was I signed up to take improvisational classes. ... And I studied that for years and I really loved it. And it's the best training I think a talk-show host can have because I love to listen to what is going on on the show and then respond in the moment. And audiences know when something is spontaneous, they just do."

On the benefit of pre-interviewing guests

"What we like to do is, we like to have areas that seem profitable, that seem promising because I think when you do a television show or a radio show, whatever you're doing, it should be a slightly heightened reality. It shouldn't just be the conversation that I would have with somebody if I bumped into them on the subway and was going to ride 40 blocks with them. It should be better than that. So in order for it to be better than that, I want to make sure that I don't go down blind alleys. When you do a pre-interview you find out: What's just going to go nowhere?"

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This is FRESH AIR; I'm Terry Gross. It's late-night week on FRESH AIR. Coming up later this week we'll hear interviews with Jimmy Kimmel, Jimmy Fallon and Questlove, whose band The Roots is moving with Fallon to "The Tonight Show." Up next, we have an interview with Conan O'Brien, who has probably had the most unusual career trajectory of any of the current late-night hosts. When he became the host of NBC'S "Late Night" in 1993, replacing David Letterman, who moved to CBS, he had virtually no on-air experience. But he did have experience as a comedy writer. He edited the "The Harvard Lampoon," then he wrote for "Saturday Night Live" and was a writer and producer for "The Simpsons."

Although it took him a while to get comfortable in front of the camera, and many critics initially gave him bad reviews, he eventually did so well on "Late Night" that he became the host of "The Tonight Show" in 2009, after Jay Leno moved to prime time. That arrangement was short-lived. A few months after Leno's show premiered, it was cancelled. He moved back to the "The Tonight Show" and pushed out O'Brien, who landed at TBS in the 11:00 p.m. slot.

This interview takes us back to 2003, a few days before O'Brien's special broadcast celebrating his 10th anniversary hosting "Late Night." Our TV critic, David Bianculli, is back with me to talk about O'Brien. But first, here's a clip from Conan O'Brien's fifth anniversary special.


CONAN O'BRIEN: Folks, here to present a highlight reel of great moments from the thousands of interviews we've done on the show are two very distinguished friends of "Late Night." One is an award-winning actor and the founder of the National Actors Theater, the other combines the classic sensibilities of a 1950s robot with the dynamic flair of a 1970s street pimp.

Please welcome Tony Randall and Pimpbot 5000.

TONY RANDALL: You know, Pimpbot, Conan's had a lot of great guests on the show over the years. As a matter of fact, I was on the very first show.

PIMPBOT: Hey, I heard you likes the young women. You a freak, daddy.

RANDALL: I was hoping for once that wouldn't be brought up. It certainly no easy task deciding which clips would be on tonight's show.

PIMPBOT: Look-y here, grandpa, I gots a 10 percent senior discount on all my ho's today. But no rough stuff, dig?

RANDALL: Tastelessness, it seems, usually gets laughs. I think we could both agree that the interviews are our favorite part of the show. So let's look at them.

PIMPBOT: I'll cut you, fool.

GROSS: That's Conan O'Brien and Tony Randall and Pimpbot, recorded in 1998. And with me to introduce our interview with Conan O'Brien is FRESH AIR TV critic David Bianculli.

David, it's late-night week on FRESH AIR. What do you think Conan O'Brien brought to late-night?


He was the thinker, I mean the real abstract, out-of-the-box. He didn't want to do anything that was in the box, I don't think. He came to late-night as a writer from "The Simpsons." And so he had done a lot of clever stuff there. I don't ever think he was the best interviewer, and some of his performance stuff went off to the strange side, but a lot of the things he did were very, very clever. And if he had done nothing but Triumph the Insult Comic Dog, I would think he'd earned his place in late-night history.

GROSS: Well, he's always had this like love of pop culture and a kind of surreal take on it, which has been really wonderful. So you were there reviewing at the beginning when he got his start coming from having been a writer on "Saturday Night Live" and "The Simpsons," better known for being behind the scenes than a performer. He took a lot of knocks from the press when he started the late-night - his late-night show. What was your first take on him?

BIANCULLI: I actually liked him. And I was...

GROSS: Good for you.

BIANCULLI: I was in the minority. I was in the minority in writing positive reviews.

GROSS: Mm-hmm.

BIANCULLI: But if you look at this as TV history, Johnny Carson was rocky his first couple of weeks and you just sort of, you let people build into the job and you look at what their strengths are and what their sensibilities are. And he had it. He had a playfulness there that was really welcome at that time.

GROSS: All right. Well, thank you for helping me introduce the Conan O'Brien interview. And let's get to it.


GROSS: This is Conan O'Brien recorded on FRESH AIR in 2003, as he was preparing for his special broadcast celebrating its 10th anniversary as the host of "Late Night."

Conan O'Brien, welcome back to FRESH AIR. In order to prepare this special, since you have a lot of clips from the history of "Late Night," you've had a look back at a lot of your old shows.

O'BRIEN: Mm-hmm.

GROSS: What are some of the things you see when seeing yourself or just seeing, you know, like sketches or interviews on "Late Night" that you didn't see at the time when you were watching the show?

O'BRIEN: It's funny. When I look at the tapes from September of 1993, I'm able to almost look at that Conan O'Brien as a different person. I'm able to disassociate myself with that person. And I have to tell you, that Conan looks really young.


GROSS: Yeah. Right.

O'BRIEN: That Conan, I mean I had just turned 30 but I look 17. And I have the voice of a 14-year-old girl.


O'BRIEN: And...


O'BRIEN: And which is, and it's funny because I look at that person now and I think to myself, you have no idea what you're in for. I always knew that this was going to be hard to replace Letterman from complete obscurity with no experience. And so when I look at that guy, I kind of feel sorry for him. I think you don't - but at the same time I think it's all, it's nice because I can look at him now and say don't worry, it's all going to work out.

GROSS: Well, you know, when you started to do the show, you had to create a TV version of Conan O'Brien. I mean I'm sure you're kind of yourself on TV...

O'BRIEN: Right.

GROSS: ...but not completely. You have to be a little larger than yourself when you're doing the show. So can you talk a little bit about figuring out who you would be, for instance, in your opening monologues?

O'BRIEN: You know, the silly, weird, abstract things that I do in the show - like pretending to pull my hips with string, or licking my eyebrows, or growling, it's stuff that I was probably doing on a playground when I was eight years old and it just comes out of me. And I guess if I have any persona on the show, it would probably be the guy who mistakenly has been given a late-night talk show, but he's going to do it anyway. You know, I always...

GROSS: Right.

O'BRIEN: I mean I don't come out in an appropriate authoritative way. I jump around. I hiss at the camera. I hide from the camera. I'll start weeping openly. I mean I do all these things that a talk show host probably shouldn't do, and for some reason that seems to work for me.

GROSS: Now, you said you were probably doing a lot of the things that you do now back in your playground days.

O'BRIEN: Mm-hmm.

GROSS: I doubt you were rubbing your nipples in the playground days.

O'BRIEN: Yeah. I was not rubbing my nipples. I don't think I had nipples then. They were added later.


O'BRIEN: I - it's a surgery you could get in Sweden. I, but I was doing the Bob Hope growl very, very early.

GROSS: Mm-hmm. Mm-hmm.

O'BRIEN: And I was...

GROSS: This is the growl at attractive women.


O'BRIEN: Exactly.

I was doing that to girls when I was eight years old because I thought, I think I saw Woody Allen do it in a Woody Allen movie and later saw Bob Hope do it. And I thought that's the funniest thing I've ever seen, so I was playing the part of the sort of bungling lothario when I was eight, nine, 10 years old. I just, basically any comedian, whether they know they're going to be a comedian or not, they're working on their act from the minute they're conscious. And...

GROSS: So it's kind of like you knew as a kid that you weren't like the leading man guy, that you were the comic lead.

O'BRIEN: Oh, yeah. I - exactly. I think that, I think everybody unconsciously or subconsciously figures out very early how they fit into the puzzle. And I think very gifted athletes, they figure that out on some level at an early age and they start asserting that part of their personality. And I figured out that I could make people laugh fairly early. I never decided that would be a career. That wasn't until I was I think halfway through college that it started to occur to me that maybe I could make a living doing something like this.

GROSS: Let's get back to Bob Hope for second. You mentioned that, you know, the growl and...

O'BRIEN: Mm-hmm.

GROSS: know, some of the self-deprecating stuff came from Bob Hope. Did you as a kid, when you saw him after seeing Woody Allen...

O'BRIEN: Mm-hmm.

GROSS: ...did you then go back and watch early Bob Hope movies and think like, this is an interesting guy...

O'BRIEN: Yeah.

GROSS: ...I'm going to learn more about him?

O'BRIEN: Yeah. It's funny because my discovery of Bob Hope was backwards - which is I first was introduced to him, like a lot of people in my generation, as he's that guy wearing a blue blazer who's telling kind of corny jokes in these sort of late, you know, mid-'70s, late '70s TV specials. Do you know what I mean?

GROSS: I sure do.

O'BRIEN: And it was only much later on that I discovered him in movies with Bing Crosby and I saw, you know, basically that he created - I think he created this prototype character that a lot of people have borrowed from. And Woody Allen admits that, you know, that after he saw Bob Hope he knew what he wanted to do for a living - that the confident/cowardly guy on the make and who will betray his best friend to get what he wants. And when I saw Bob Hope do that I sort of slowly started to realize that, gee, a lot of the people who I really enjoy watching - Peter Sellers is a good example, Peter Sellers in the "Pink Panther" movies.

GROSS: Mm-hmm.

O'BRIEN: Here's a guy who's, you know, completely wrong and completely confident. And I always thought that that's, that was a comedic persona that always appealed to me, is - for some reason. I think it touched sort of, or tapped into my idea of who I was, which is I'm the person who's going to growl at the actresses on my show and hiss at them. Or if Harrison Ford is on the show I'm going to have a mock bravado with him that completely collapses the minute he gives me one of those cold stares. And it's, you know, it's a sort of comedy dynamic that's old and tried and true, but in a talk show format it's a little different.

GROSS: Did you behave around girls as a teenager the way you do around the real like attractive actresses on your show, where you'd growl at them and be like the comic guy?

O'BRIEN: Sadly, yes because...


O'BRIEN: And I'm being serious about that because if you're, you know, if you grew up the way I did, you know, and you're fairly repressed Irish Catholic, you're too scared to try anything, do you know what I mean? You're not going to try anything, so it comes from an element of truth, which is you're attracted to them, you're fascinated by women, you want to make them laugh, you want to get a reaction from them, you want them to like you. So there's all the bag of tricks but then God forbid any of them ever, you know, made a move towards you or showed interest, then you'd run for the hills. So that's, you know, kind of where the whole persona came from.

You know, I think you always had that idea with Bob Hope, that if he ever got Dorothy Lamour he wouldn't know what the hell to do with her. You know, he'd be panic-stricken.

GROSS: Mm-hmm. How much did the Irish Catholic background figure into your identity? I mean how repressed where you?


GROSS: Or, you know, how...

O'BRIEN: This is turning into a therapy session.

GROSS: Yeah. How...

O'BRIEN: I'm going to get a bill from NPR.


O'BRIEN: The repression is all there. It's real. It's, you know, it fuels the depression and the self-hate.


O'BRIEN: It's a wonderful - it's like a Rube Goldberg device, you know, the depression drops down onto the self-hate...


O'BRIEN: ...which triggers the self-loathing, which then fuels the anger, which curdles into comedy, and then it sadly leads to a slow, quiet drinking problem.


O'BRIEN: It all fits. It's like a Swiss watch the way it interrelates. No, I, you know, I joke a lot about the, you know, there's an element of truth to everything I say and then I exaggerate.

GROSS: Right.

O'BRIEN: Because, yeah, a little repressed but, you know, I didn't take it too far, you know, I had a good time, if you know what I mean.




O'BRIEN: I can't stop doing that. I'm sorry.

GROSS: Well, you have all these weird - you have a whole repertoire of weird laughs.

O'BRIEN: I know. I'm sorry.


GROSS: And I figure you must've watched a lot of...

O'BRIEN: I have crazy...

GROSS: You must've watched a lot of horror movies too.

O'BRIEN: Yeah. You know what's funny? I watched a lot of everything. I just literally watched everything there was to watch and I took from everybody and everyone everywhere - commercials, you know, jingles, a funny thing I'd see on a Christmas special. If you see something you like, you grab it and you throw into the stew and you mix it up. And I used to, I remember we first started doing the show, one of the first characters that I did on the show was called the Laughing Genie. And it was just, I was a genie that just laughed way too much. You know, that hands on hips Yul Brynner.


O'BRIEN: And, but, so, yeah, I collect all those things and I, one of the things that I always do is if I pass a mirror, even if I'm brushing my teeth in the morning, you know, I'm busting stuff out, I'm trying things. I'm always trying to make my wife laugh and it's a sad, never-ending cry for help.


O'BRIEN: If there are any listeners out there who can please help me. Someone help me.

GROSS: We're listening back to our 2003 interview with Conan O'Brien. Here's a clip from one of his opening monologues that year.


O'BRIEN: I'm the late-night cat. Meow.

You'll never hear that phrase again. I promise you.

You'll never ever again hear the late-night cat. That was a terrible mistake. It'll never happen again. It'd be great if NBC seized on that and started using it. And after Leno, Late Night Cat.


O'BRIEN: That's as much promo time as I get now. This is Conan. Jay Leno's got more. (unintelligible) He said this, he said that, and then Conan.

(Unintelligible) They get an auctioneer in there just for that line. Could we bring the auctioneer in for the Conan promo? All right. Here he goes: (unintelligible).

GROSS: We'll hear more of my interview with Conan O'Brien after a break. This is FRESH AIR.


GROSS: It's Late Night Week on FRESH AIR. Let's get back to our 2003 interview with Conan O'Brien. Let's talk about the most famous character that's come out of the show which is Triumph, the insult comic dog.

O'BRIEN: That's right. Uh-huh.

GROSS: Which is, I think, a Robert Smigel...

O'BRIEN: Yes, Robert Smigel...

GROSS: ...a Robert Smigel creation.

O'BRIEN: ...who's the original head writer of the show. Mm-hmm.

GROSS: Right. And who does the voice for Triumph.

O'BRIEN: Mm-hmm.

GROSS: Who had a big fight with Eminem. Did Smigel tell you that he was going to do that and did you say, no, no, no, no, Eminem is going to fight you for it, it's going to be dangerous?


O'BRIEN: I knew that he was going to do it and most people react pretty well to Triumph. Triumph became so popular that we started getting celebrities requesting Triumph. Jon Bon Jovi called up and said, please, can Triumph come over and insult me?


O'BRIEN: And we literally had people requesting it. It was a high honor. So Eminem, I think, was the first person to get, you know, angry at the puppet. Which I love saying. I love that someone can get angry at a puppet.

GROSS: I figured he'd never seen the show and had no idea what was going on.

O'BRIEN: I don't know.

GROSS: He'd never seen your show and had no idea what Triumph was.

O'BRIEN: Right. I have no idea. I have no clue.

GROSS: Yeah.

O'BRIEN: But, you know, it's - yeah, it's possible he thought he was just being attacked by a man with a rubber dog on his fist. I don't...


O'BRIEN: I love that his bodyguards intervened. That was the best part. So it's a good thing he had three bodyguards on hand to protect him from the rubber dog.

GROSS: Can you talk about the evolution of Triumph on your show?

O'BRIEN: Yeah. I might get this wrong because things are - things get complicated, but the best that I can remember is that we used to do a recurring routine on the show about talented animals from the Westminster Dog Show. And we would say, you know, some of these animals are really talented and we actually have some of them here in the studio. And we would cut to a little puppet theater.

And we had these little dog and cat puppets that would do silly little tricks like, you know, spinning a plate on a stick. Or doing card tricks. I mean, just - it was silly and it was - people seemed to like it. And I guess there was an idea to do a comedian. And, you know, so Robert said what if - yeah, I think he was an insult comic. So Robert just started playing around with that.

And we tried that and right away it was very funny, you know. And my favorite part about Triumph, and I don't know why but Triumph has the voice of a Ukrainian woman.


O'BRIEN: You know, you think - it's like: It's so nice to see you. Yas. Yas. Oh, yas. And I have no idea why but apparently this is, you know, an immigrant who made his way to the Borscht Belt and it was funny right away. And then we started - I think initially Triumph just insulted me and then we thought that's really funny. Let's bring Triumph back and have him insult celebrities who are sitting next to me.

So after I was done interviewing them I'd say would you like to meet Triumph, the insult comic dog? And then he would start yelling at William Shatner and saying: Look at you, Shatner. What has happened? You're fat pig, Shatner.


O'BRIEN: And then we realized, OK, this is working really well. People really love this. And then we sent Triumph to an actual Westminster Dog Show where he attacked different dogs and got thrown out of the Westminster Dog Show. Thrown out. Kicked out because they saw this. And those are not people with a sense of humor. So men in bowties who later ended up working for Eminem converged on Triumph and threw him out.


O'BRIEN: Threw him out of the Westminster Dog Show. We snuck back in with fake credentials the next year, got thrown out again after shooting a remote. Those did very well. And then there was a period of time where people thought, well, Triumph has run its course. That's it. I think it's done. It's not going to be that funny again.

And then someone had an idea - one of our writers noticed that there was this long line outside the "Star Wars" premier of "Star Wars" fans waiting to go in. All dressed as the "Star Wars" characters. And so someone had the idea let's send Triumph there. So we sent Triumph with some of our writers and everybody wrote lines.

And that, I think, and I am not an arrogant person but I do think Triumph in line attacking different "Star Wars" fans is probably the funniest 10 minutes of television that's been on the air in the last, you know, five, eight years. I mean, it just - we showed that and the reaction was amazing. And we're going to be showing a big piece of that on the 10th anniversary show. It's really one of the...

GROSS: Oh, great.

O'BRIEN: of the greatest things, you know, I ever saw. And I love television. I've watched a lot of television. And I just thought, you know, Triumph is talking to a man dressed as Darth Vader, you know, and insulting him.

GROSS: What did he say?

O'BRIEN: And - the guy as Darth Vader is explaining which buttons do what. Like this button is my transporter and this button does this and this button does that. And Triumph says: Yes, yes, and which button do you press to call your mother to come pick you up?


GROSS: We're listening back to our 2003 interview with Conan O'Brien. We'll hear more after a break. This is FRESH AIR.


GROSS: It's Late Night Week on FRESH AIR. Let's get back to our 2003 interview with Conan O'Brien.


GROSS: I love your description about how the interview, the conversation, you have on TV should be a heightened reality. It should be better than the conversation you'd have on the train with someone. But when you run into somebody on the train do they expect that you're going to have that kind of heightened conversations that they're used to hearing you do on TV?

O'BRIEN: Well, first of all, let's get something straight. I will not ride the subway.

GROSS: Yeah, I knew as I was saying that you probably don't ride the subway.


O'BRIEN: It's ridiculous. I've had a strap handle put in my limo so I can have that subway experience but in the comfort of a limousine.


O'BRIEN: I don't even know. Subways, are they steam powered still? I don't remember. It's been so long.

GROSS: Do you have homeless people asking you for money in your limo so you could get the full experience?

O'BRIEN: We hire a guy to act like a homeless person. And I pay him $85,000 a year.


O'BRIEN: He's a graduate of Brown University and it's a good job for him. The misconceptions that people have about me. One, is that for some reason people think I'm not very big. So whenever I go anywhere all I hear is, oh, my god, I can't believe you're this tall. You don't look this tall on TV. How are you that tall? Why do you look so small on TV?

And the other thing is that I'm so up and sort of - I think on television I'm a cartoon character. Do you know? I really think that I've got the big hair and the big grin and I jump around a lot. And I'm kind of like this hyperactive Bob's Big Boy character.


O'BRIEN: And so when I'm walking down the street or if I'm on the subway or if I'm taking a cab, a lot of times people ask me what's wrong? Are you OK? You see sad. And I'm not sad, I'm just neutral. You know?

GROSS: Yes. Yes, yes.

O'BRIEN: And my line is a straight - my mouth is a straight line. There's no downward curve whatsoever. It's an exact straight carpenter's line. Because I'm thinking and I'm, you know, wondering what I'm going to have for lunch or where I'm going to take my dog for a walk or, you know, where my wife and I are going to go on vacation. It's just like I'm just completely neutral. But when people know me from the television show, neutrality reads as depression.

GROSS: So it's not so much the conversations, it's how you look that gets people.

O'BRIEN: Yeah.

GROSS: Yeah.

O'BRIEN: It's funny because I actually make an effort if I'm talking to - if I'm talking to someone on the subway or if I'm talking to someone, you know, when I'm getting my bicycle repaired at the bike shop, I actually make a little bit of an effort. You know, I'm always trying. Especially if someone's laughing. I think that's probably revealed how needy I am.

No matter where I am, if it's 3:00 in the morning and my car breaks down and someone from AAA comes on a country road to fix it and I say something and the person laughs, I start working it a little bit.


O'BRIEN: I want to get that second laugh. And I want to get that third laugh. And it's the AAA guy and he doesn't need to hear this. But, you know, it's hard to turn that off. You know, I'm always killing with, like, Chinese food delivery guys. You know?

GROSS: Well, Conan O'Brien, thank you so much for doing the show.

O'BRIEN: Thanks a lot for having me.

GROSS: Conan O'Brien recorded in 2003. Our Late Night series continues through the week. Each day the latest interviews from this archival series will be added to our Late Night theme page and available for downloading on our website Transcript provided by NPR, Copyright NPR.

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