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Late night talk show host Conan O'Brien

Late night talk show host Conan O'Brien celebrates ten years on the air Sunday September 14, 2003, with a primetime special on NBC. In 1993, he moved into the Late Night host slot when David Letterman went to CBS. Prior to Late Night, O'Brien was a writer for Saturday Night Live and writer and producer for The Simpsons.

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DATE September 8, 2003 ACCOUNT NUMBER N/A
TIME 12:00 Noon-1:00 PM AUDIENCE N/A
NETWORK NPR
PROGRAM Fresh Air

Interview: Conan O'Brien discusses his 10 years as host of "Late
Night" and his upcoming anniversary special
TERRY GROSS, host:

This is FRESH AIR. I'm Terry Gross.

Conan O'Brien is celebrating his 10th anniversary as the host of "Late Night"
with a prime-time special that will air next Sunday on NBC. Sure, now many of
us think he's incredibly funny and we think that his show is a good reason to
stay up late and cheat on sleep. But when he was hired in 1993 to replace
David Letterman, who had moved to CBS, few people thought he'd last this long.
O'Brien had written comedy, but had no on-air experience. As a Harvard
student, he edited the humor magazine The Harvard Lampoon, then he wrote for
"Saturday Night Live" and was a writer and producer for "The Simpsons." But
you could tell he wasn't used to being in front of a camera.

We invited Conan O'Brien to look back on the past 10 years. First, let's hear
a clip from a recent monologue.

(Soundbite of "Late Night")

Mr. CONAN O'BRIEN (Talk Show Host): (From "Late Night") Man, if this is
possible, it's getting crazier in California. That place is retarded now, I
believe.

(Soundbite of applause)

Mr. O'BRIEN: I mean, they just really are. It's just--the whole state of
California--you've seen my impression, right?

(Soundbite of insane laughter)

Mr. O'BRIEN: That's my impression of the state of California.

(Soundbite of insane laughter and applause)

Mr. O'BRIEN: The whole state's gone mad.

Well, it's getting even weirder now. It's been reported that some of Arnold
Schwarzenegger's opponents have been circulating naked pictures of Arnold on
the Internet.

(Soundbite of cheering)

Mr. O'BRIEN: That's right. Yeah. True story. Yeah, in a related story,
Arnold is leading the other candidates by four inches.

(Soundbite of applause)

Mr. O'BRIEN: You get it?

(Soundbite of laughter)

GROSS: Conan O'Brien, welcome back to FRESH AIR. Congratulations on your
10th anniversary. Did you expect to celebrate a 10th anniversary of "Late
Night"?

Mr. O'BRIEN: I actually thought we'd make it eight years and then the whole
thing would fall apart. So this is quite a shock. That was all we had
planned. I'm very specific in my schemes and plans, and I always thought,
eight years, four months, and then the whole thing goes under.

You know, to tell you the truth, I never thought about it that much. I
always took it one show at a time. And I'm still doing that. And I think
that's how you get anything done, is you just--all I ever thought about, from
the first day was, `Let's just see if I can do one show.' And then after that
I said, `OK, let's see if I can do two. Let's see if I can do three.' And
now it's been about 1,800 shows and it's 10 year...

GROSS: But who's counting?

Mr. O'BRIEN: Exactly. Yeah. I'm like a man on one of those New Yorker
cartoons on the little island, you know, counting the days. But, yeah, it's
been 10 years and it's pretty mind-blowing.

GROSS: Can you give us something of a preview of the anniversary show?

Mr. O'BRIEN: The anniversary show is gonna be a 90-minute extravaganza.
It'll be a juggernaut. I'm just trying to think of great words to describe
90 minutes of television.

GROSS: Stupendous--yeah.

Mr. O'BRIEN: Stupendous...

GROSS: Are you usually confident or insecure when you're facing a big event
like your special?

Mr. O'BRIEN: Here's my formula. I like to be extremely insecure, and then
that insecurity drives me to work very hard and worry a lot. And that causes
me to almost overprepare to the point that right when I get up to the event,
I'm ready to go and I'm feeling pretty good. And that's kind of the formula
I've used for everything that I've done in show business. Last year, when I
hosted the Emmys, I did that. I was very worried about it, worked very hard
until just before I went out to host, and I knew that I had all my ducks in a
row and I was ready to go. And I was heavily medicated, which also helps.

GROSS: Yeah, are you good at dealing with anxiety, even if you're putting
that anxiety into the work?

Mr. O'BRIEN: Yeah. I have--you know, it helps me--anxiety works for me when
it spurs me to work and to think hard. This is a terrible person to quote,
but I'm gonna do it anyway. Someone told me once that Charles Manson--Charles
Manson once said...

GROSS: We get all of our self-help adages from Charles Manson.

Mr. O'BRIEN: Yeah. Charles Manson once said about comedy--no, he once said,
you know, `Fear is a good thing because it makes you hyper-aware.' And I
thought, well, that's interesting because I found that anxiety and fear, to a
certain degree, actually helps you prepare and helps you focus and helps the
creativity. The problem is--it's like anything else--that if it gets out of
control, suddenly you're nervous, you freeze up, you're not thinking, and you
don't do your best work. So it's just trying to hit just that right balance
where you're kind of worried about it and you're thinking about it a lot and
you're obsessing on it and it's making you creative and not getting in the
way.

GROSS: In order to prepare this special, since you have a lot of clips from
the history of "Late Night," you've had to look back at a lot of your old
shows. 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?

Mr. 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.

Mr. O'BRIEN: And that Conan--I mean, I had just turned 30 but I look 17. And
I have the voice of a 14-year-old girl. 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,' because I always knew that this was gonna be hard and I
always knew that it was gonna 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 gonna be. 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 nice, 'cause I can look at him now and say, `Don't worry,
it's all gonna work out.'

GROSS: Now when you heard your voice back then, you didn't think you sounded
like a 14-year-old girl, did you?

Mr. O'BRIEN: No, then I thought I sounded like Barry White. No. It's only
later on that I see, oh, OK, I was pretty green, I was very raw, and...

GROSS: No, no, you were very pale, which you still are.

Mr. O'BRIEN: I was very pale. That actually didn't get any better. That's
still--unfortunately, lack of melanin, there's nothing medical science can do
about that. But what I like when I look at those old shows is that, from the
very first day, we were swinging for the fences, which I--and I like that. I
like that we always tried, I thought, fairly innovative, strange, weird
comedy pieces, even when it wasn't working or it wasn't very popular with
people. And now some of those routines have become very popular. And
they've almost become, you know, mainstream in a way. And it's fun to look
back and see the show when we were trying these things for the first time and
it, you know, looked very bold.

GROSS: What was the high point and low point of the very first show?

Mr. O'BRIEN: The first show, I remember the--wow, there's a lot of--I don't
remember there being a low point in the first show. The first show I
remember feeling I was so happy to do it because they announced that I had
the show in late April of '93, and I went on the air in September. And for
those few months in between, I was very famous, but for no reason. And I
hated that. I hated being famous for no reason. And everyone was looking at
me as if to say, `What are you going to do? Who are you?'

GROSS: Mm-hmm.

Mr. O'BRIEN: `What is this?' And so I was so happy to do the first show
because I thought, now, love me or hate me, they know what it is I do. Do
you know what I mean? They can actually look at the work rather than just
staring at me for no reason. And so I remembered really liking the first
show.

I think the low point was probably when the show was over realizing that there
was this elation that we did it, we did our first show, and then realizing
this doesn't end. I have to do this tomorrow and the next day and the next
day and the next day and the next day. And this is much harder than I
thought.

And the high point was probably singing "Edelweiss" with Tony Randall at the
end of the show.

GROSS: Conan O'Brien is my guest. And his 10th anniversary "Late Night"
special will be shown September 14th. It's a 90-minute prime-time special.

Let's take a short break here, then we'll talk some more. This is FRESH AIR.

(Soundbite of music)

GROSS: My guest is Conan O'Brien, and he's celebrating his 10th anniversary
with a special, a 90-minute prime-time special Sunday night, September 14th.

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...

Mr. O'BRIEN: Right.

GROSS: ...on TV 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?

Mr. O'BRIEN: It's funny, because a lot of it--a lot of the good stuff, if we
want to qualify any of it as good stuff, is unconscious. Never set out--you
know, these silly, weird abstract things that I do in the show, like
pretending to pull my hips with string or, you know, 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 has mistakenly been
given a late-night talk show, but he's going to do it anyway. You know? I
always...

GROSS: Right.

Mr. O'BRIEN: I mean, I don't come out in an appropriate, you know,
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. I doubt you were...

Mr. O'BRIEN: Mm-hmm.

GROSS: ...rubbing your nipples on the playground days.

Mr. O'BRIEN: Yeah, I was not rubbing my nipples. I don't think I had nipples
then. They were added later. It's a surgery you can get in Sweden. I--but I
was doing the Bob Hope growl very, very early. And I was...

GROSS: Mm-hmm. Mm-hmm. This is the growl at attractive women.

(Soundbite of O'Brien growling)

Mr. O'BRIEN: Exactly.

(Soundbite of O'Brien growling)

Mr. O'BRIEN: 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, you know, 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 gonna 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.

Mr. O'BRIEN: Oh, yeah. Exactly. 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, you know,
people that are very verbal figure that out early. And I think I, when I was
very young, said, `OK, what do I have? You know, I come from a big family,
I'm one of six. All my other brothers and sisters have these different
talents. What do I have and how do I fit into this, you know. And on the
playground, what can I offer? What's different about me?' And I think, you
know, it's a defense mechanism and you figure out very quickly, what do you
have in your arsenal. And I figured out that I could make people laugh fairly
early. I never decided that would be a career. That wasn't till 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 a second.

Mr. O'BRIEN: Mm-hmm.

GROSS: You mentioned that, you know, the growl and...

Mr. 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...

Mr. O'BRIEN: Mm-hmm.

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

Mr. O'BRIEN: Yeah.

GROSS: ...I'm gonna learn more about him?

Mr. 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.

Mr. 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, after he saw Bob Hope, he knew what he
wanted to do for a living, that the confident--slash--cowardly guy on the make
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. Here's a guy who's, you know,
completely wrong and completely confident.

And I always thought that 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's 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, 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 teen-ager the way you do around the
real attractive actresses on your show, where you'd growl at them and be like
the comic guy?

Mr. O'BRIEN: Sadly, yes, because--and I'm being serious about that because,
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 were you? Or, you know, how...

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

GROSS: This is turning--yeah.

Mr. O'BRIEN: I'm going to get a bill from NPR. The repression's all there,
it's real. You know, it fuels the depression and the self-hate. It's a
wonderful--it's like a Rube Goldberg device, you know. 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. No, 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.

Mr. 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.

GROSS: OK.

(Soundbite of laughter)

Mr. 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.

Mr. O'BRIEN: I know. I'm sorry. (Laughs)

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

Mr. O'BRIEN: I have crazy...

GROSS: You must have watched a lot of horror movies, too.

Mr. O'BRIEN: Yeah, you know what's funny? I watched 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
it into the stew and you mix it up. And I used to--I remember when 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 `Ha-ha-ha-ha-ha!' So,
yeah, I collect all those things. And one of the things 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. If there are any listeners
out there who can please help me. Someone, help me.

GROSS: Conan O'Brien will be back in the second half of the show. His 10th
anniversary special airs Sunday in prime time on NBC. Here's a clip from his
fifth anniversary special.

I'm Terry Gross, and this is FRESH AIR.

(Soundbite of "Late Night with Conan O'Brien")

Mr. O'BRIEN: I'm excited. 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 Theatre. The other combines the classic
sensibilities of 1950s robot with the dynamic flair of a 1970s street pimp.
Please welcome Tony Randall and Pimpbot 5000!

(Soundbite of cheering and applause)

Mr. TONY RANDALL (Actor): You know, a Pimpbot...

(Soundbite of laughter)

Mr. RANDALL: 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 5000": Hey, I heard you likes the young womens. You a freak, daddy!

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

"PIMPBOT 5000": Lookie here, Grandpa, I gots a 10 percent senior discount on
all my hos today, but no rough stuff. Dig?

(Soundbite of laughter)

Mr. 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 5000": I'll cut you, fool.

(Soundbite of music)

(Announcements)

GROSS: Coming up, the opening monologues, going solo without a sidekick, and
Triumph the Insult Comic Dog. We continue our conversation with Conan
O'Brien.

(Soundbite of music)

GROSS: This is FRESH AIR. I'm Terry Gross back with Conan O'Brien. He's
celebrating his 10th anniversary as the host of "Late Night" with a prime time
comedy special this Sunday on NBC.

Here's a clip from one of his opening monologues earlier this year. O'Brien
is jumping around and meowing like a cat.

(Soundbite from "Late Night")

Mr. O'BRIEN: I'm the "Late Night" Cat. Reowr. You'll never hear that phrase
again, I promise you. You'll never again hear `The "Late Night" Cat.' That
was a terrible mistake. It'll never happen again. Be great if NBC seized on
that and started using it. `And after Leno, "Late Night" Cat.' That's as how
much promo time as I get now. `And here's Conan.' `Jay Leno's got (speaks
nonsense syllables). He's also got this, and he's got that. And then Conan.'
(Speaks nonsense syllables). 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.' (Speaks nonsense syllables).

OK. Let's analyze exactly what's going wrong there. You know what's funny is
that...

GROSS: Yeah?

Mr. O'BRIEN: ...when we first started doing the show, I was trying so hard to do
the monologue correctly and do a good job and be a professional. And what's
funny is that at a certain point, I gave up, and I think that's when the
monologue became compelling and original, because it does rely on good jokes.
I do try and get the best jokes I can. I have very good monologue writers who
do a really good job. But where I really come to life is when one of them
completely misses. And that's where I light up, because if a joke misses
completely, a lot of the other late-night shows like to have music play in
between the jokes to kind of fill it out. Do you know what I mean?

GROSS: Mm-hm.

Mr. O'BRIEN: And I always told the band, `Never play anything in between the
jokes,' because there's nothing funnier than a comedian saying something, and
then there's absolute silence, especially, I think, with me, because I've
built up this persona over time. I mean, I think those are the best
monologues is when people see me backed into a corner, and I have to fight my
way out.

GROSS: Can you think of a good example of one of those?

Mr. O'BRIEN: Sadly, I can think of hundreds and hundreds of examples. I think,
you know, sometimes what I'll do if a joke gets absolutely nothing, and I'll
tell a joke, and it gets absolutely nothing, is I'll pause, and then stare
into the camera, and then there'll be a little bit of applause afterwards.
And I'll stop the audience and say, `I don't need your pity,' you know. And
then I'll pause again and say, `Actually, I do need your pity.' And then they
really applaud. And you're just playing a game in a way. I'm turning the
audience into a foil, and we're just going back and forth.

And you know, I think the best thing that I ever did is 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 is I went and signed up to take improvisational
classes in improv. 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's going on in the show and then respond in the moment. And
audiences know when something's spontaneous. They just do. Do you know what
I mean?

GROSS: Mm-hmm.

Mr. O'BRIEN: You know, it's not a terrible disaster if we try something at
12:30 at night on my show and it doesn't work.

GROSS: And then you can make fun of it afterwards.

Mr. O'BRIEN: Then I can make fun of it, and I can acknowledge it. The most
important thing to do is acknowledge that it didn't work. Don't pretend it
worked and keep moving, because that's where I think you alienate people.

GROSS: Now that gets to a change that's recently happened, happened in the
past few years, which is that, you know, for the first few years of the show,
you had Andy Richter as your sidekick, your co-host.

Mr. O'BRIEN: Yeah, yeah.

GROSS: And he's acting now. He was back on your show recently, and he'll be
with you for the 10th anniversary show.

Mr. O'BRIEN: That's right.

GROSS: But it's harder, I imagine, to reflect on what's happened on the show,
or what's gone wrong and make a joke about it without somebody there to work
off of, to bounce it off of.

Mr. O'BRIEN: It's funny, because at first I thought, `Well, we're going to
have to get somebody else.' And I was dreading that, because I thought Andy
was not there by design. Andy was a happy accident. Andy was someone who I
interviewed for a writing position, and we hired him, and then, over the
course of the summer just realized, `This person needs to sit next to me. We
have a nice chemistry.' So I didn't want to go and try and have lightning
strike again in the same place. And I was skeptical about that, so when Andy
left, I didn't really know what to do. And I thought, `Well, let's just have
a period where we have mourning, where there's nobody there.' 'Cause I
thought the worst thing in the world would be if Andy leaves and people tune
in the next night and someone else is sitting in his chair, it's going to feel
wrong. It's going to almost feel disrespectful. So we didn't do that.

And then I started to realize over time that I was just looking into camera,
and I was talking right into the lens, and I was using the audience and my
producer and everybody around me as kind of my collective foil. And it felt
like, `Well, this is a change. This is very different, but it works in a
different way.' And we went from being open to the idea of a sidekick to
realizing, `Well, gee, it's been three years since he's been on the show, and
we've done a lot of really good work, and things seem to be all right, so
let's keep going.'

GROSS: There's a lot of, you know, ripped-from-the-headlines type of humor,
as they say, in your monologue. Do you read the newspaper every day?

Mr. O'BRIEN: Yeah. I read The New York Times, 'cause that's what gets
delivered. And then I'll flip through, you know...

GROSS: I like the way you're not taking responsibility for the fact you're
reading The Times. You're reading it only because it's delivered.

Mr. O'BRIEN: Yeah, it's delivered. I've asked them not to bring it. I've
said, `Please, don't bring The New York Times.' No, that's the one, you know,
I get at the house, and so that's the one I read most thoroughly.

GROSS: Right.

Mr. O'BRIEN: And then I'll read USA Today, because they have the colored pie
charts, and that really breaks it down nicely for me. And then after that, we
have so many different papers, then, you know, I'll pick up The Washington
Post and see what catches my eye. So you look through a bunch of different
papers, and so do all the writers. It is funny, though. Of all the
late-night shows, I think ours is probably the least topical of all of them.
It's the most abstract. We do a lot of comedy that's just about people in
bear suits and with puppets, you know. Our show has topical comedy, because
it helps fuel ideas every day, but I'm shocked at how, I think, there's a good
70 percent of our show that you could look at over the years that relates to
absolutely nothing. It's like we've created a little wonderland of characters
and oddballs, and it's almost like a "Pee Wee's Playhouse." It's, like, I
often think we're more like a children's show sometimes than a late-night
topical talk show.

GROSS: Well, let's talk about the most famous character that's come out of
the show, which is Triumph, the Insult Comic Dog...

Mr. O'BRIEN: That's right.

GROSS: ...which is, I think, a Robert Smigel creation.

Mr. O'BRIEN: Yes, Robert Smigel, who is original head writer of the show.

GROSS: Right, and who does the voice for Triumph 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's going to fight you for it. It's going to be
dangerous?'

Mr. 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 `Please, can
Triumph come over and insult me?' 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.
He had never seen your show, and had no idea what Triumph was.

Mr. O'BRIEN: Right. I have no idea. I have no clue. But, you know, yeah,
it's possible he thought he was just being attacked by a man with a rubber dog
on his fist. I love that his bodyguards intervened, and that was the best
part. So it's a good thing that he had three bodyguards on hand to protect
him from the rubber dog. But...

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

Mr. O'BRIEN: Yeah, I might get this wrong, because 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, it was silly, and people seemed to like it. And I guess
there was the idea to do a comedian. And you know, so Robert said, `Well what
if--I think he was an insult comic?' And 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, you know. You think, it's like, `It's so nice to
see you, yes, yes, oh, yes.' And I have no idea why, but apparently, you
know, this is, you know, an immigrant who made his way to the Borsch 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
say, `Look at you, Shatner. What has happened? You're fat pig, Shatner.'
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 started humping real dogs, and we got one of the dogs to
hump him, 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 bow ties, who later ended up working for Eminem, converged on Triumph
and 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. It think it's done. It's not going to be that
funny again.' And then someone had the idea, one of our writers noticed that
there was this long line outside the "Star Wars" premiere 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, we showed that, and
the reaction was amazing, and we're going to be showing a big piece of that in
the 10th anniversary show. It's really one of the great...

GROSS: Oh, great.

Mr. 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?

Mr. O'BRIEN: 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: My guest is Conan O'Brien. More after a break. This is FRESH AIR.

(Soundbite of music)

GROSS: My guest is Conan O'Brien, and he's celebrating the 10th anniversary
of "Late Night With Conan O'Brien." And so there's going to be a 90-minute
prime time special Sunday night, September 14th.

Mr. O'BRIEN: It's going to be a sextravaganza. I just made that word up, but
I think that's what it's going to be.

GROSS: You have guests on the show each night. And you know, we have guests
on our show all the time, of course. And when we don't know much about
somebody who we're thinking of having on the show, one of the producers will
often call them up and pre-interview them. And we almost feel, like, almost
guilty about it, like we're kind of almost, like, auditioning them for the
show.

Mr. O'BRIEN: Right.

GROSS: So I feel a little uncomfortable about it, but we always say, `Well, I
bet the "Today" show does that and more, you know. I bet, you know, David
Letterman, I bet Conan O'Brien puts their guests through real hoops before
they get on the show.' What do you do? How do you screen guests before
they're on the show if they're not people who are really known to you?

Mr. O'BRIEN: Well, we do have segment producers who talk to them on the
phone. And, you know, some people think, `Well, but that's, you know,
cheating, because shouldn't it just be a real conversation?' And what I
believe is that it has to be--there's a happy medium, which is, I don't
believe in trying to turn normal people or people who aren't necessarily
raconteurs or funny people into comedians. So I'm uncomfortable having people
tell a prepared whopper of a story with a big punch line at the end, because a
lot of people can't do that very well. Do you know what I mean?

GROSS: Yeah.

Mr. O'BRIEN: You know, you've seen people try, and I think it's painful, so
what we like to do is we like to have areas that seem profitable. Do you know
what I mean? 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. Do you know what I mean?

GROSS: Yes.

Mr. O'BRIEN: 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. And so in order for it to be
better than that, I want to make sure that I don't go down blind alleys. And
when you do a pre-interview, you find out what's just going to go nowhere. Do
you know what mean? And, you know, if J.D. Salinger decides he wants to come
on my show and talk about what he's been working on for the last 30 years, and
I say, `Great. Well, first of all, I want to ask you, tell us about your
house.' `I don't like talking about my house. We're not talking about my
house.' Well, I don't want to have that moment on the air. Do you know what
I mean?

GROSS: Yes.

Mr. O'BRIEN: I want to make sure that we've at least found out, you know,
J.D. Salinger loves making balloon animals, and he's really funny talking
about balloon animals. And so I'll bring that up. And then he and I can
probably have a really great three-minute moment talking about balloon
animals.

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?

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

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

Mr. 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. 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
can get the full experience?

Mr. O'BRIEN: We hire a guy to act like a homeless person, and I pay him
$85,000 a year. 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 I think on television, I'm a cartoon character, you
know. I really think that I've got the big hair and the big grin. I jump
around a lot. And I'm kind of like this hyperactive Bob's Big Boy character.
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 will ask me, `What's wrong? Are you OK?
You seem sad.' And I'm not sad. I'm just neutral, you know.

GROSS: Yes, yes, yes.

Mr. O'BRIEN: 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, you know.

Mr. O'BRIEN: Yeah, it's funny, because I actually make an effort when 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, and 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. 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: My guest is Conan O'Brien. More after a break. This is FRESH AIR.

(Soundbite of music)

GROSS: Conan O'Brien is my guest, and he's celebrating the 10th anniversary
of "Late Night With Conan O'Brien" with a 90-minute prime time special on
Sunday, September 14th.

Now you're married now, and I believe you're expecting a baby?

Mr. O'BRIEN: That's right, yeah, sometime probably around October 15th.

GROSS: Do you feel ready to be a father?

Mr. O'BRIEN: You know, I don't think you're ever ready.

GROSS: Yeah, right.

Mr. O'BRIEN: I'm excited about it, and I'm ready to try and be a good dad.
But I'm very aware that around October 15th, I am going to be hit over the
head with a giant two-by-four, and that I have no idea what it's going to be
like or how I'm going to respond. I'm going completely on faith that it's
going to be great, because, you know, I think it will be. I just believe it
will be, but I have no idea what it's going to be like. I think people with
children just know something that the rest of us don't know.

GROSS: Right. I guess you're about to find out what that is.

Mr. O'BRIEN: I'm about to find that out, and then I'll come and tell you.

GROSS: Thank you, yes.

Mr. O'BRIEN: I'll report back, because it's very intense and crazy, the idea
that I, along with my wife, will be responsible for a human life.

GROSS: Well, the interesting thing, too, is that, let's face it, you got
married just to prove you're not gay.

Mr. O'BRIEN: Well, that was the idea. This was all my manager's idea. He
said, `We've got to prove you're not gay.' And so we tried this, and that
didn't work apparently. And then we decided, `OK, now we got to crank it up,
and we got to have the baby.' So a baby was purchased and will be, quote,
"born" on the 15th, 'cause I ain't having sex. That freaks me out.

GROSS: How did you end up doing a lot of jokes about not really being gay and
stuff like that on your show?

Mr. O'BRIEN: It just seemed so absurd. And it goes back to, you know--it's
so funny, 'cause there's a lot of people out who are uncomfortable with, you
know, the idea of someone, you know, even implying for a second that they
might be gay. And I'm just not uncomfortable about it at all. Do you know
what I mean? I've sort of just thought it's, you know, just another way--it
sort of fed into my insecure bumbling, you know, guy who's constantly trying
to convince the ladies that he's got it going on. Do you know what I mean?
So every now and then, in the monologue, there'll be a huge news story that's
going on that day, and I'll come out and, of course, `Of course, folks, you
all heard the big news.' And then I'll just pause and, `I'm straight,' you
know. And for whatever reason, people just laugh, you know. But who knows?
I don't really know. Like, you know, it's going to be years before I really
know what my sexuality is. Ultimately, it's not important. We're all people.

GROSS: Well, Conan O'Brien, congratulations on your 10th anniversary. And
congratulations on your forthcoming baby.

Mr. O'BRIEN: Thank you.

GROSS: And I look forward so seeing the special. It sounds like it will
really be great. Thank you so much for doing the show.

Mr. O'BRIEN: Thanks a lot for having me.

GROSS: Conan O'Brien's 10th anniversary special airs Sunday night in prime
time on NBC.

(Credits)

GROSS: I'm Terry Gross. We'll close with a song by Warren Zevon. He died
yesterday of lung cancer. He was 56. Rock critic Ken Tucker will have a
remembrance tomorrow. This song is from his new CD "The Wind" which he
recorded in his home studio when he was sick.

(Soundbite of music)

Mr. WARREN ZEVON: (Singing) Shadows are falling, and I'm right out of breath.
Keep me in your heart for a while. If I leave you, it doesn't mean I love you
any less. Keep me in your heart for a while. When you get up in the morning
and you see that crazy sun, keep me in your heart for a while. There's a
train leaving nightly called when all is said and done. Keep me in your heart
for a while. Sha-na-na-na-la-la-la-la-la-li-lo. Keep me in your heart for a
while. Sha-na-na-na-la-la-la-la-li-lo. Keep me in your heart for a while.

Sometimes when you're doing simple things around the house, maybe you'll think
of me and smile. You know, I'm tied to you like the buttons on your blouse.
Keep me in your heart for a while. Hold me in your thoughts. Take me to your
dreams. Touch me as I fall into view. When the winter comes, keep the fires
lit, and I will be right next to you. Engine driver's headed north to
pleasant's dream. Keep me in your heart for a while. These wheels keep
turning, but they're running out of steam. Keep me in your heart for a while.
Sha-la-la-la-la-la-la-la-li-lo. Keep me in your heart for a while.
Sha-la-la-la-la-li-li-li-li-lo. Keep me in your heart for a while.

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