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

August 27, 2013

Guests: Jay Leno - Conan O'Brien

TERRY GROSS, HOST: This is FRESH AIR. I'm Terry Gross, back with the second day of our late-night week. Later this week, we'll hear from Jimmy Kimmel, Jimmy Fallon and Questlove, who leads the band The Roots, and will be moving with Fallon to "The Tonight Show" early next year. Later in today's show, we'll feature an interview with Conan O'Brien.

First, we have an interview with Jay Leno recorded in October 1996, after the publication of his memoir "Leading with My Chin." Leno succeeded Johnny Carson as the host of "The Tonight Show" in 1992. Although it's a position he'd always dreamed of, he left "The Tonight Show" in September of 2009 to start his own primetime show in NBC, and Conan O'Brien became the new host of "The Tonight Show."

But, just a few months later, in January of 2010, Leno's show was cancelled. In a very controversial move, he returned to "The Tonight Show," leaving O'Brien without a TV home, until a few months later when O'Brien started a new late-night show on TBS. Next February, Leno will leave "The Tonight Show" for the second and, we assume, final time, and it will be Jimmy Fallon's turn to take over.

Before we hear the interview, our TV critic David Bianculli is going to talk about Jay Leno's contributions to late-night TV. Hey, David, welcome back.

DAVID BIANCULLI, BYLINE: This is fun. I'm glad to be here.

GROSS: Yeah. And you brought a clip to get us started, before hearing the Jay Leno interview. What did you bring?

BIANCULLI: This is Jay Leno's first appearance on the old "Tonight Show." What's great about hearing these old clips is that you can hear that they're going over with the audience. And these are people - nobody knew who Jay Leno was, and he's out there in a horrible '70s suit, but he had good jokes.

(SOUNDBITE OF TV SHOW, "THE TONIGHT SHOW")

JAY LENO: David Jansen's commercial for Excedrin: The man looks like a headache.

See, when I was a kid, we were never allowed to have headaches. See, my folks grew up during the Depression, so consequently, they make you feel very guilty about everything, you know. I mean, even now, I go home for a weekend, hey dad, pass the salt. We never had salt when we were kids. We had to live without salt. We didn't have underwear, potatoes. We ate dirt every day of the week. Your mother and I hunted wild dog for food. We had nothing when we were your age.

GROSS: That's Jay Leno in 1977, his first appearance on "The Tonight Show." Now that Leno is preparing to leave "The Tonight Show," for real this time...

BIANCULLI: Again, yeah.

GROSS: ...yeah. How would you describe his place in late-night TV?

BIANCULLI: Well, what he ended up doing was finding and acceptable average. I mean, when he started, when he was up against Letterman, Letterman beat him for the first couple years. But then once Leno came ahead, he was unstoppable. He never lost that audience. And the reason why NBC did all the dumb things it did with primetime and bringing him back is because Jay Leno had numbers that nobody else was getting. And so he was very successful.

And I think he was successful at being middle-of-the-road, at being a broadcast comic, which is what "The Tonight Show" certainly was under Johnny and under Jack Parr and under Steve Allen. And he did continue that.

GROSS: So middle-of-the-road wins the big numbers.

BIANCULLI: Well, it does, except the numbers are shrinking now, and the audience is changing now, and how much of a television program they're watching or whether they're even watching it on television is changing now.

GROSS: You told me a great story that I'd like you to tell our listeners. You interviewed Leno when he was in that transition, leaving "The Tonight Show" and preparing to host his new 10 o'clock primetime show.

BIANCULLI: Yeah. He's kind of wary of the press. I mean, it's pretty much a given that more people prefer Letterman to Leno, and he feels the heat of all of that. But I started off the interview by reading a couple of quotes of people basically saying this new guy is never going to match the old guy, and "The Tonight Show" is just a shadow of what it was, and I don't know what NBC was thinking.

He's going, how many more of these am I going to have to hear? And I read him two or three. And then I said these are from 1962, when Johnny Carson took over for Jack Parr. And suddenly he lightened up, I mean, completely, and he sort of talked about the idea that, in history, when a popular host leaves and another one comes in, no matter how good that person may be, there's a learning curve and there's a resistance. So he got that part of his place of history.

GROSS: So, David, why don't we hear the interview that I recorded with Jay Leno? This was back in 1996, just before his program celebrating his fifth anniversary as the host of "The Tonight Show."

BIANCULLI: OK.

GROSS: Jay Leno, welcome to FRESH AIR.

LENO: Thank you.

GROSS: Like most young comics, your ambition when you were starting out was to eventually get onto "The Tonight Show."

LENO: Yeah.

GROSS: What was the most memorable part of your first shot on "The Tonight Show"?

LENO: Most memorable would be - well, I got heckled my first shot, which was a horrible experience. But luckily, I'd worked a lot of clubs, so I could deal with that, and Johnny seemed to like that. But our producer, Fred de Cordova, you know, he would say to you, OK, here's the deal. He would come over, and he would say - and Fred was somewhat of a legendary figure, having, you know, directed Jack Benny and all these people.

He would say: After you do your standup routine, if I go like this, waving my hands towards me, that means come over and sit down to Johnny. If I put my hand up like this, stay on your mark. If I wave you away, go behind the curtain. But whatever you do, don't move until you get my signal. I said yes, sir.

I walk out. I do my routine, and thank you, good night, big laughs, thank you, thank you very much. I look over, and I see Fred about to signal me, and his phone rings. I see him, hello. Now he's talking. And I don't know what to do. And the audience is now getting into that (clapping), you know, we're down to that odd one or two clap. And I'm still standing there.

So the applause picks up a little bit more, as if people are going, oh, all right, just get lost, will you, you know. And I'm going hi - and he's talking away, you know, da, da, da, da, da, da. Now the applause has all but stopped. Fred puts the phone down, he looks over, completely forgetting - oh, come here, come on, oh, thank you.

You know, I realize it was only maybe six, seven seconds, but, of course, to me I might as well have been up there an hour and a half at this point, just hanging, waiting to get Fred's signal to come over and sit down next to Johnny. So that was pretty scary.

GROSS: On your first shot on "The Tonight Show" with Johnny Carson, did he laugh at your jokes?

LENO: Yeah, he was very good, actually. He was a terrific audience. I mean, that's what the "The Tonight Show" is. It's not trying to get the audience to laugh. It's trying to get Johnny to laugh.

GROSS: Right, right.

LENO: But, you know, the audience gets the cue from the host.

GROSS: Right.

LENO: And if Johnny is laughing, they're enjoying it more.

GROSS: Did Johnny Carson give you advice about your standup act, or later on about guest hosting or hosting when you took over?

LENO: Not so much about hosting, but he did about, you know, the first time I did "The Tonight Show" - well, actually, I was the guy that was sort of the last of my graduating class to do "The Tonight Show." By graduating class, I mean all the guys I sort of started with: Robin Williams - and, well, not Robin, I mean, Letterman and, oh, guys like George Miller and so many of the comics. They all did it before me.

And, you know, Johnny came in one night at The Improv to see me. Harvey Korman brought him in, and, you know, there are two kinds of comedians. There are comedians that have a lot of attitude, and not many jokes. There are comedians that have a lot of jokes, but not much stage persona.

By attitude, I mean those kind of comics who can get on stage and go, hey, pal. Nice hat. All right? What did you win - somebody guess your weight? You know, that kind of thing. And they're loud and they're boisterous, and they're just funny in their nature, but there are no jokes.

And then there are other comedians like, well, you take a guy like Steven Wright, who are just natural joke writers, you know, very monotone. They tell the joke a certain way. And to me, the best comedians are the ones that combine both those elements. You have a joke, and you have an attitude.

I remember Johnny came to see me, and he said, you know, he thought I was funny, but I wasn't ready for the show because my jokes were too far apart. You know, I didn't quite understand what he meant, but I listened. And then I started watching his monologue, and I realized, you know, he's doing 15 or 20 jokes in a space where I was doing five.

I mean, I could get on stage and - being sort of physically big and loud and imposing - I could get a laugh where there wasn't any, but that really - that was great for a nightclub, but not for TV. You know, the idea being, on television, if the joke doesn't work, your funny attitude will carry you through. And if your funny attitude doesn't carry you through, your joke will carry you through. And if they both work, you've got a killer joke, you know.

GROSS: Now, how do you work up your opening monologue?

LENO: How?

GROSS: Well, and how do you feel - and also, how do you feel about having writers writing with you? I'm sure during the years that you were doing clubs, you were writing all your own material, and I would think it would...

LENO: I was writing all my own stuff. And there's this arrogance that a lot of comedians had, and I certainly have it, or at least had it. You know, I can do this. I can handle it. I mean, like, the first 15 to 20 times I hosted "The Tonight Show," I said I don't need cue cards. I'll memorize it. And I did OK.

But then I realized this is ridiculous. If you're going to this every day, you can't memorize, you know, 11-and-a-half minutes worth of jokes. I mean, you'll go nuts. You'll go crazy trying to do this. And then I gradually got into it. And now the way it works is we tape the show from five to six, and then we have a meeting. I go home at maybe 7:30, 8 o'clock.

Nine o'clock, I start to put the monologue together. Eleven o'clock, Jimmy Brogan, he's the guy that works with me on the monologue, we go through maybe 500 or 600 jokes that we've prepared that day, or everybody's prepared. And they're not all jokes. Some are just punch lines. Some are just setups. Some are: did you hear about the guy who did this odd thing in Iowa, question mark. You're trying to make a joke out of that.

Sometimes it's a complete joke from a writer. Anyway, we'll try and put at least half the monologue together by two or three in the morning. And then I get into work about 8:30, and through the course of the day, and you're writing jokes constantly as you're picking the red M&Ms out of some rock group's, you know, dressing room because, whatever, you know, you're still dealing with show business people.

GROSS: We're listening back to a 1996 interview with Jay Leno. We'll hear more after a break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: It's late-night week on FRESH AIR. Let's get back to our interview with Jay Leno, recorded in 1996 after the publication of his memoir, "Leading with My Chin," in which he wrote about his early days in comedy.

When you were starting in comedy, there weren't comedy clubs yet, not as we know them. Some of the venues that you played included retirement homes, prisons, mental hospitals. This is through a state program in Massachusetts. I think you got like 10 bucks for a performance?

LENO: We used to get 10 bucks a show to do old people's birthday parties for the state. We used to do prisons. I did a show at, like, Walpole State Prison. And prisoners are not a good audience, you know, because comedy is based on a certain civility. How folks. How are you?

You know. And when you got a guy sitting in the front row and he's got a little blond kid on a choke chain, wearing underpants, sitting on the floor next to him, that's not an ideal audience, you know?

GROSS: What material would you do in your prison...

LENO: You just do your regular act. I only had my act growing up, whatever. You know, I used to do these psychiatric homes and, you know, they'd get like -you know, and this is not to make fun of psychiatric patients, but you know, you go, hi, everybody, how you doing? And then, like, in the middle of your act there'd be a guy in the corner going...

(SOUNDBITE OF SCREAMING)

LENO: And then orderlies would come in - this would just break the mood of the whole room, you know. Hey, anybody here from Boston?

(SOUNDBITE OF SCREAMING)

LENO: You know, hey, hey, calm down there, fellow. How you doing? You know... Oh.

(LAUGHTER)

GROSS: Well, did this give you confidence, performing in front of people who either...

LENO: Well, it was fascinating because you realized - it wasn't until I performed at, like, this place Lenny's on the Turnpike in Boston that I ever got a professional audience.

You know, I could always say in my own mind, well, you know, the audience, it's a psychiatric hospital. They didn't laugh because there's obviously something wrong with them.

GROSS: You could say - right, if they don't laugh, they're crazy.

LENO: Yeah. It was like strip clubs.

GROSS: Yeah.

LENO: When I play strip clubs, they wouldn't laugh or applaud or do anything. But it gave you the confidence just to stand on stage because the people weren't paying any attention to me anyway. I mean there's a story in the book about playing this club called the Mineshaft where - it was in Minnesota. People would pay $5 to get in, and then for another $5 the customers would get a miner's hat with a light on it.

Now, there were no lights in the club. It was just a big empty building. And then women would come out and dance. And of course the guys had the lights on their heads, and they would look at whatever part of the women they wanted to look at with the light, and I would just be standing in the darkness, telling jokes. Hi, everybody. How you doing?

Occasionally somebody would look over at me, and I couldn't even look at them because they had the bright light on their head. So if they looked at me, ow, it burned my eye. I had to look away. So most of the time, for the whole week I was just standing in darkness while guys looked at these women with those miner's hats on.

GROSS: You were probably one of the most hardworking comics in show business when you were getting started, just performing anywhere and everywhere to get experience. But sometimes you'd get billed - you'd get booked in really inappropriate places. And my favorite story about that is when you were booked, I guess it was a Catskill resort at a Hassidic, at an Orthodox Jewish resort.

LENO: Yeah, there was this...

GROSS: And you were booked as, what, tonight Jay Leno, Jewish storyteller.

LENO: I was billed as a Jewish storyteller.

GROSS: What did you do?

LENO: This agent in New York would come into the clubs, and he'd say I need a comic this Saturday, it pays $50, you know. And I remember one time, before I get to that story, this guy sent me up to a job, and it paid $100 for the weekend. And I thought, well, that's pretty good, $100 for the weekend.

And I remember afterwards, the owner of the hotel came over and said, boy, that was very good. You know, normally we don't like to spend $1,200 on an act, but we really enjoyed you. And I realized the agent took $1,100 commission out of my $100.

(LAUGHTER)

LENO: You know, it was just a nightmare. Anyway, that the last time I worked with him. The first time, he sends me to up the Catskills at the La Chaim(ph) Resort or something like this. And I said, what is it? Just a nightclub. I said what kind - I said is it mostly - oh no, you go up there.

So I finally find this place, and it's all these cabins way back in the woods, nice people, but it's a Hassidic resort. And I pull in there, and it says on one of those - one of those bad signs, you know, you pull on a trailer, and it's got the flashing lights around it, tonight Jay Leno, Jewish storyteller.

So I get there, and I walk out onstage, and it's all Hassidic. You know, and I don't even speak Hebrew, you know. And I said there's been a big mistake, you know, I'm not really a storyteller, I'm not even Jewish. The guy made a mistake - da da da. And this guy said, oh, do your act, let's hear what you do, you know.

(LAUGHTER)

LENO: So I did my - and they were very nice and, I mean they were polite. You know, you just - I felt bad for them, and they felt bad for me, and they were nice people. It just, it wasn't what they had bought, you know. It was a horrible job.

GROSS: You know, I think it's funny, in your book you talk about how when you were getting started in comedy, or maybe this was even before you got started, when you were growing up, the comics meant adult guys, usually from New York, usually Jewish, who spoke more to your father than they spoke to you.

LENO: That's true. When I was a kid, you had Alan King, you had Rodney Dangerfield, and these guys were always funny, but they always came from the point of view, at least to me, was these kids today with the long hair, you can't tell the boys from the girls, I'll tell you. You know...

(LAUGHTER)

LENO: And all that was funny. My father would laugh at that. And then I remember seeing Robert Klein and George Carlin and David Brenner and Steinberg, and these guys would come out, and suddenly I noticed I was laughing more than my dad because their humor was coming more from my point of view, especially Robert Klein.

He was a guy who was, I felt, like me: middle-class, normal parents, not (unintelligible) not rich, not poor, just normal, you know, watched the same TV shows as a kid that I watched, Joked about the same kind of things that I watched. And that was a big change in comedy, at least for me.

GROSS: So how did you figure out where you material was going to be?

LENO: I figured it out from watching those guys. You know, I said to myself, boy, these guys make fun of the same kind of things that I think are funny. These are the same things I talk about with my friends. I mean prior to them, I don't think you would have seen Alan King come on "The Ed Sullivan Show" and do jokes about Jimi Hendrix. You know, it just didn't - you know, it didn't happen.

(LAUGHTER)

GROSS: No, it would be about Jimi Hendrix mowing his lawn.

LENO: Right, right, Jimi Hendrix with the hair like that, you know. But I mean, suddenly here were guys on mainstream television talking about things only kids - you know, now adults by Rolling Stone albums, you know what I'm saying? But back in the '70s, there were adult records, you know, you had Henry Mancini and Frank Sinatra, and then you had, for the kids, you know, The Rolling Stones and The Beatles, whatever. And nobody ever did jokes about The Beatles on mainstream television.

These were the first comedians to sort of parody younger people's lifestyles.

GROSS: You know, we were talking about how hardworking you were as a young comic, just trying out everything that you could, playing every place you could play. When you moved to Los Angeles, you moved there before you had a home, before you had any money, and you often ended up just, like, sleeping on the steps to the comedy clubs or sleeping in the alleys behind comedy clubs.

LENO: Yeah, I used to get picked up in L.A. for vagrancy. And what the cops would do is they'd just put you in the back of the car, and you'd just drive around with them on their shift all night. And being a comic, you know, this worked, well, somewhat to my advantage, but actually no. The first time I got picked up, you know, they'd see you, let's move along, where do you live?

I don't kind of live anywhere. All right, get in the car. What do you do? I'm a comedian. Oh yeah? Tell us a joke, you know. So then you'd sort of try and come up with every dirty joke you could think of to tell these cops all night, and har, har, that was - and that worked pretty good. Well, they let me go.

But then two or three nights would go by, and the cops would go, hey, are you that comedian guy our partner picked up the other night? Yeah. Get in the car. All those jokes you were telling - so, you know, two or three nights a week I'd have to ride around until dawn telling jokes to different cops because they would say, hey, have you seen that kid on the street, pick him up, he's got some funny jokes.

GROSS: It must be strange for you, knowing so many comics so well and having been in the position of being a young hardworking comic, really wanting their big break, to now be the guy who could give a young hardworking comic a big break.

LENO: Oh man, it's a nightmare.

GROSS: And I'm sure you don't want to hurt anybody's feelings. On the other hand, you want to have the best show you possibly can. So it's probably a really awkward spot.

LENO: Oh, it's horrible because I used to think, well, now that I'm hosting "The Tonight Show," I can go anywhere. But now you can't go anywhere because you walk in and go, oh gee, there's Larry, I've got to hide, you know.

(LAUGHTER)

LENO: I mean that's what it is. I mean, you know, you have friends that come up to you that - you know, when I first got the job, men, women, comedians would come up to me and they'd go, hey Jay, you know, Johnny would never put me on, but now you've got the show, it'll be great, man, I can come on all the time.

And I'd have to say but you know, if you weren't good enough to get on with Johnny, it's not good enough to get on with me. You've got to make it funnier. And you know, I lost a lot of friends that way. I mean it's just they're people that I love dearly as friends, but the material is not strong enough, or maybe it's really old-fashioned, you know. It's just, you know, old jokes about, I don't know, hippies or airline food or whatever it is.

And you just say, you know, you've got to update the stuff. And they just don't get it.

GROSS: Jay Leno, recorded in 1996. He leaves "The Tonight Show" in February. Our late-night series continues in the second half of the show. Each day the interviews from our late-night series will be added to our late-night theme page and available for downloading on our website, freshair.npr.org. I'm Terry Gross and this is FRESH AIR.

TERRY GROSS, HOST: 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.

(SOUNDBITE OF TV SHOW, "LATE NIGHT WITH CONAN O'BRIEN")

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?

DAVE BIANCULLI, HOST: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.

BIANCULLI: OK.

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.

(LAUGHTER)

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.

(LAUGHTER)

O'BRIEN: And...

(LAUGHTER)

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.

(LAUGHTER)

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.

(SOUNDBITE OF GROWL)

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: ...you 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...

(LAUGHTER)

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?

(LAUGHTER)

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.

(LAUGHTER)

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

(LAUGHTER)

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

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

GROSS: OK.

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

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.

(SOUNDBITE OF TV SHOW, "LATE NIGHT WITH CONAN O'BRIEN")

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.

(LAUGHTER)

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.

(SOUNDBITE OF MUSIC)

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?

(LAUGHTER)

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?

(LAUGHTER)

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...

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

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: ...one 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?

(LAUGHTER)

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

(SOUNDBITE OF MUSIC)

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

(SOUNDBITE OF ARCHIVED INTERVIEW)

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.

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

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 freshair.npr.org.

Transcripts are created on a rush deadline, and accuracy and availability may vary. This text may not be in its final form and may be updated or revised in the future. Please be aware that the authoritative record of Fresh Air interviews and reviews are the audio recordings of each segment.