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PIERS MORGAN TONIGHT

Interview With Conan O'Brien

Aired June 25, 2012 - 21:00   ET

THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.


PIERS MORGAN, CNN HOST: Tonight, my exclusive with Conan O'Brien. A rare interview with the late-night legend.

(BEGIN VIDEO CLIP)

CONAN O'BRIEN, TBS's "CONAN": There's nothing more comical than the sight of me without my clothes on.

(END VIDEO CLIP)

MORGAN: His comedy, his life, his loves. Now Conan tells all.

(BEGIN VIDEO CLIP)

O'BRIEN: Is any of this going to get in the papers, do you think? This won't get out.

(END VIDEO CLIP)

MORGAN: Conan O'Brien as you've never seen him before.

(BEGIN VIDEO CLIP)

O'BRIEN: We often go to the spa together.

MORGAN: Not now.

O'BRIEN: All right.

MORGAN: Come on.

O'BRIEN: It was your idea.

(END VIDEO CLIP)

MORGAN: Conan O'Brien and he doesn't hold back.

(BEGIN VIDEO CLIP)

O'BRIEN: That's the dumbest thing anyone has ever said to me, Piers. And I mean that in the nicest way.

(END VIDEO CLIP)

MORGAN: And tonight, the question I just had to ask. How many times has he been properly in love?

(BEGIN VIDEO CLIP)

O'BRIEN: I'm just giving you the answers that are going to make it all OK. Don't screw with this, OK?

(END VIDEO CLIP)

MORGAN: This is PIERS MORGAN TONIGHT.

Conan O'Brien is very tall. He's very talented. He's very Irish. He's also perhaps the funniest man with red hair on the entire planet. He's also an ordained minister, an author of what's been voted the fourth funniest "Simpsons" episode of all time. All while hosting his own late-night show on TBS.

You are a man of many talents, aren't you?

O'BRIEN: Yes, I am. Thank you so much for telling that.

(LAUGHTER)

O'BRIEN: You didn't even scratch the surface. I have a high falsetto, beautiful, I sing like an angel. I'm hairless. Completely hairless on my body.

MORGAN: Yes.

O'BRIEN: There's many things. I'm aerodynamic. There's nothing I can't do.

MORGAN: What is the -- what is the genuinely weirdest thing about you that nobody knows?

O'BRIEN: Wow, that's a good one. The weirdest thing about me that nobody knows. I can be amusing at times.

(LAUGHTER)

O'BRIEN: Seems to have escaped people's notice.

MORGAN: You don't do many interviews.

O'BRIEN: I don't do a lot.

MORGAN: I've been trying to lure you for like, you know, 18 months. I've appeared on your show endlessly.

O'BRIEN: Yes.

MORGAN: In a desperate attempt to lure you in.

O'BRIEN: I don't do a lot because, think about it, I'm on television constantly. Since 1993, I'm on TV for a chunk of time every day. I'm not looking for more ways to be on television. And no one in America seems to want me to be on more. (LAUGHTER)

O'BRIEN: So I -- I'm trying, if anything, pull it back. But I couldn't resist this. You have this beautiful Lucite desk. It's very nice. I think of classy airport lounge. It's beautiful. But I'm thrilled to be here.

MORGAN: I'm thrilled you're here. I'm a huge fan, as you know. Now take me back to the first moment you made somebody laugh. Do you remember it?

O'BRIEN: Yes, it was about four years ago.

(LAUGHTER)

O'BRIEN: I remember it very well. It was my wife. We've been married at that point for seven years. Let's see. I think -- I don't remember the exact moment. My mother claims that as an infant I had mashed up some food in my high chair and was throwing it around and laughing and it was making my mother laugh and that her brother, my uncle, said, don't laugh, it's going to make him think he's a comedian or something. And -- that it caught on there.

But you know I think it always starts with the family. It starts with the family. I'm from a large Irish Catholic family. And trying to -- the benchmark for me is trying to make my dad laugh or trying to make my brothers laugh at the table when we were having meals together.

MORGAN: Where do you come in the pecking order of the kids?

O'BRIEN: We're not sure. We're always finding new ones.

(LAUGHTER)

O'BRIEN: I walk into the bathroom and -- I'm Liam. Oh, we don't think we met.

(LAUGHTER)

O'BRIEN: There are six of us. I'm third from the top, fourth from the bottom. So I have two older brothers, two younger sisters and a younger brother.

MORGAN: And what do they make of being related so closely to the Coco phenomenon?

O'BRIEN: They -- you know, I think it's -- my brother, Luke, looks a lot like me. He -- we -- Luke and I look very similar and we're only about a year apart and he lives in Boston. And he said many times he'll just be walking -- he told me once he was walking to a store to, you know, to buy, you know, some embarrassing product that he probably doesn't want me to mention on the air. He has a rash on his ass that's chronic.

Luke, I'm sorry. And, Piers, I think you asked me specifically what was his ailment. But anyway, he said he was walking and that people sometime follow him and will follow him into a store, and he'll have to turn and say --

MORGAN: I'm not him.

O'BRIEN: No, I'm not him. I'm the smarter -- he is actually. He's the smart one in the family. He's -- Luke's a genius.

MORGAN: Your family, you're a very close family.

O'BRIEN: Mm-hmm.

MORGAN: You're still close. I mean you speak --

O'BRIEN: We're still close. I talk to someone in my family at least every day. And what's great about my family is they don't care that I'm on television. They don't care. They -- we all make fun of each other. And they're very happy. I don't know. In your country, I think it's take the piss out of someone.

MORGAN: Yes.

O'BRIEN: They love to do that. They love to do that. So --

MORGAN: Which is not -- it's not a very common thing in American psyche to take the piss as we call it like that.

O'BRIEN: Yes.

MORGAN: Sarcasm isn't a massively advanced part of the American humor. I don't think.

O'BRIEN: It is in different -- it is in different parts. It depends on where you're from. In Boston, it's a very strong thing. In Boston, they love to take you down a peg the second you show up back in town. It's something about that place. And it's what I love about Boston.

This is a true story. I showed up in Boston once a couple of months ago. And I landed at Logan Airport. And I get out and there's a cab line because I'm going to take a cab to my parent's house. So I'm headed towards the cab line. And long before I even get a chance to get to the back the cab line, this guy sees me coming. And he just -- and he's the guy that runs the cab line. He goes like, hey, back of the line, TV star.

(LAUGHTER)

O'BRIEN: And I said, I was headed to the back -- yes, you're like the rest us now, pal, you know. That's where I was headed. But there's -- they don't even give you the chance. It's they need to take you down a notch right away.

MORGAN: When you were young, apparently in the third grade --

O'BRIEN: When I was younger. MORGAN: Younger, my apologies.

(LAUGHTER)

MORGAN: You apparently --

O'BRIEN: I'm 26.

(LAUGHTER)

MORGAN: Even in third grade, you did Charlie Chaplin impressions.

O'BRIEN: Yes, yes.

MORGAN: And you said to your parents as a kid, mom and dad, I'm going to be in show business, I need to learn to tap dance.

O'BRIEN: Yes, true story.

MORGAN: I love that line.

O'BRIEN: Yes. I had this very -- television in those days very different from TV now but in the 1970s, they -- there's only a couple of channels. And the UHF stations, Channel 38 and Channel 56, all their programming is showing old movies. That's what I watched. I grew up on old movies. My parents wouldn't let me go see --

MORGAN: What was it, Gene Kelly, Fred Astaire? Was it that kind of --

O'BRIEN: Yes, I was watching -- I was watching old gangster movies. Love those. "Angels with Dirty Faces" and Humphrey Bogart films. But yes, with that movie, "That's Entertainment" came out, it's showing you what entertainment is. I thought like an idiot I -- in the 1970s thought that that was what entertainers needed to have to know. You have to be like Donald O'Connor and Gene Kelly. You've got to know how to sing, dance, move. You've got to know how to do it all.

So I marched up to my parents and I said, I need to know how to tap dance. And they all -- they thought all kinds of things. But they said OK. Let's call him on his bluff. And they found me this really old African-American gentlemen who was a fantastic -- named Stanley Brown who said -- who had been the protegee of Bill "Bojangles" Robinson. And he lived in in this -- lived -- worked out of this dilapidated studio. And taught all these, you know, people how to dance.

I was the only white kid there. Not only that, I was tiny and I had bright orange hair. So all these beautiful black women are learning jazz, tap, and all this kind of stuff. And then I would march in with my box of shiny shoes. Like, hi, everybody, let's get started. Come on, let's do it, see. You know?

(LAUGHTER) O'BRIEN: And then he would work with me. And so my parents, god bless them, they were great that way. My dad's a microbiologist and a scientist. My mom was a lawyer. And they said this is what he wants to do. And --

MORGAN: Have they ever regretted helping you get into show business?

O'BRIEN: I think no. I think -- I'm sure they have since.

MORGAN: I mean your mom in particular. I know that my mother, when it's going great, it's obviously fantastic. When things don't go so well, and you're so high profile and you get hammered, mothers hate that.

O'BRIEN: Yes. Yes.

MORGAN: They feel it very personally.

O'BRIEN: Mothers don't like it. But my parents, the second I was paying my own rent they didn't care what I did anymore. That's just true. The minute -- I think if I had, you know, when I paid that first rent check of my own right after I got out of college and I moved out, and I started paying my own rent, I think if I had said, by the way, you should know, I'm a hired assassin. We don't care. Kill who you need to kill.

MORGAN: When you -- began in show business, was part of the allure of it being famous if you're honest, when you look back to that time?

O'BRIEN: I have to say -- and this is true of a lot of comedians and I've talked to other comedians and heard them say the same thing, and I defy anyone to deny this. For most of us, it's getting girls to notice us. It really is. And, and it's -- it's still probably on some level.

I'm very happily married. Two kids. But there is something initially especially in those early days. You notice -- you go through the check list in your mind of what do I have that might interest a girl. And I didn't have much. I would go through the list. I'm not a good athlete. My skin's not -- go down the list. The hair's a little silly. The name is weird. And then I got to -- they laugh.

When I start joking around, they laugh and they hang around a little bit. So probably that's the initial -- if I'm going to be brutally honest, it was just to get --

MORGAN: Just to get girls?

O'BRIEN: Just to get -- not even, I don't even -- to get them. To get them to look at in my direction, Piers. I'm taking it down to a much more basic level. You know?

MORGAN: You moved to L.A. after Harvard. Come to your Harvard commencement speeches in 2000.

O'BRIEN: Yes. Yes.

MORGAN: It's one of the classic commencement speeches.

O'BRIEN: And you said it was number -- that was the fourth greatest. Have they ranked the commencement speeches? I'm very competitive.

MORGAN: I think you've got to be number one on the commencement speech. You're fourth on the list of "Simpsons" episodes.

O'BRIEN: That I can accept.

MORGAN: Yes.

O'BRIEN: That speech --

MORGAN: This is top drawer.

O'BRIEN: All right.

MORGAN: When you went through Harvard, everything much have seemed like it was all going swimmingly. And like most comedians I've interviewed, you've got no agony, no torment, no pain.

O'BRIEN: That's --

MORGAN: Your father wasn't stubbing cigarettes in your face.

O'BRIEN: That's the dumbest thing anyone's ever said to me, Piers. And I mean that in the nicest way. Yes, tons of agony. It's very hard to look at someone's life in the -- in the abstract --

MORGAN: Where was your agony?

O'BRIEN: Insecurity. A feeling that I don't deserve to be where I am. For example, I think when I went to -- I worked very hard in high school. That's the dirty little secret about me as I was not -- I was always a very hard working student. And wanted to go to a good school and worked really hard to go to a good school. And then when I got there, immediately had the fear that a lot of people had which is I don't belong here.

These are the people that know a lot more than I do. They're smarter. I'm the fake. I'm the phony. And I think that is the common denominator you see with a lot of people. Artists or performers. They don't think they belong.

MORGAN: You still feel it?

O'BRIEN: Yes, I feel it today. I -- I wasn't sure they'd let me in here. There's a -- there's a constant --

(LAUGHTER)

MORGAN: Is it the pressure to be funny? I mean that must be a very particular --

(CROSSTALK)

O'BRIEN: You know --

MORGAN: (INAUDIBLE) keep pressure.

O'BRIEN: It's funny, the -- it's odd or ironic, whatever you want to call it, but my desire -- getting into comedy was a very beautiful accident. Because I worked very hard at everything. And I tried really hard. Comedy was something that I stumbled into when I was in college. I'd wanted to be a performer. And then thought, this is never going to happen. I'm from Brookline, Massachusetts.

My parents said, we don't know anybody in show business. I'm not going to get into show businesses. This is a ridiculous dream. So I kind of gave up on it and became a really good student. And then accidentally stumbled into the college humor magazine. And it was like falling off a log and discovering what it is that I was meant to do. I loved it. I absolutely loved it.

And I thought -- I had never valued being funny that much. I just thought, oh, that's something I do with my friends. And then suddenly I saw that it has some cachet in the real world. And that these older students really seem to like the stuff that I'm writing. And they seem to think I'm funny and they want to put me in charge of this place. So a lot of that changed my outlook on what I could do for a living.

MORGAN: So you're at Harvard.

O'BRIEN: Yes.

MORGAN: You're doing brilliantly. You're making people laugh. Everything's going great. Let's take a short break because after the break it all goes horribly wrong.

O'BRIEN: Sex change. Sex change when we return.

MORGAN: I didn't want to mention it first.

O'BRIEN: I was a girl. I was a boy. Now I'm --

(LAUGHTER)

(COMMERCIAL BREAK)

(BEGIN VIDEO CLIP)

O'BRIEN: I took a lot of criticism. Some of it deserved. Some of it excessive. And I'll be honest with you, it hurt like you would not believe. But I'm telling you all this for a reason. I had had a lot of success. I had had a lot of failure. I looked good and I looked bad. I've been praised and I've been criticized. But my mistakes have been necessary --

(END VIDEO CLIP)

MORGAN: You wrote this incredible commencement speech at Harvard particularly year 2000. And I want to sort of tell the story of what happened to you after you left Harvard through the prism of the speech because it was -- it was a wonderful life template, I think, for anyone who is considering life after college. You said, you see, kids, after graduating in May, I moved to Los Angeles. I got a three- week contract at a small cable show, I got a $380 a month apartment, a terrible dump. I bought an awful car. You said it was a car that -- Isuzu?

O'BRIEN: The Isuzu --

MORGAN: Isuzu.

O'BRIEN: It's something called the (INAUDIBLE) which --

MORGAN: They only manufactured for a year because they found out technically it's not a car.

O'BRIEN: No, it was -- I don't know what it was. It was a hair brush more than it was a car.

(LAUGHTER)

O'BRIEN: A terrible car.

MORGAN: But you go work on a show for a year. And you must be thinking, I'm a Harvard graduate, I've got on the show, life is beautiful.

O'BRIEN: I'd love to pretend that's what I thought. But I never feel that way. Anyone who knows me will tell you I never think we're in good shape now. I've never done that. But yes. I -- I got that job and then as I said in the speech my writing partner at the time and I lost that job. And then a lot of series of misadventures and highs and lows.

MORGAN: At one stage, you're sent to the Santa Monica (INAUDIBLE) and Wilson's House of Suede and Leather.

O'BRIEN: Yes.

MORGAN: And you're sitting there thinking how did a Harvard graduate end up here.

O'BRIEN: Yes. But you had -- I had those thoughts many times where you -- and Los Angeles is a very -- when you don't have a job in Los Angeles, there's something about it that's more profoundly depressing than maybe not having a job other places.

MORGAN: Well, because they're all around you, are success stories.

O'BRIEN: Yes. And --

MORGAN: Billboards.

O'BRIEN: Yes. Everything.

MORGAN: Everything. The whole machinery of the city.

O'BRIEN: Exactly.

MORGAN: Is geared to achievement, success. Not failure.

O'BRIEN: Right.

MORGAN: I mean when it's great, it's the best place to be in the world. When it goes wrong, it's the most lonely place on earth.

O'BRIEN: Also in this town, when you walk on a sidewalk, you're perceived as a failure. When you -- and so -- what happens is if you --

MORGAN: If you walk you're perceived as a failure.

O'BRIEN: Exactly. So I just was -- you know, you can -- you can walk on three blocks in this town and people will pass you, who know you, and say, that's too bad what happened to Conan.

L

O'BRIEN: I guess, you know, he's -- they -- it's not like New York or any other city in that way. You just -- so yes, that was a very -- there's lots of intense kind of despair.

MORGAN: You then get a big break. "Saturday Night Live."

(BEGIN VIDEO CLIP)

MIKE MYERS, "SATURDAY NIGHT LIVE": I believe this gentleman has something to say.

O'BRIEN: Well, I just completed your course. I never dreamed I could be this handsome. Thanks, Lange.

MYERS: You're handsome. Give that man a round of applause.

(END VIDEO CLIP)

MORGAN: And after a year and a half, they read your sketches, they give you a two-week tryout. The two weeks turned into two seasons. You think, I've made it.

O'BRIEN: Right.

MORGAN: And I'm "SNL" superstar. And you get so cocky, you think, I'm going to go and write my own TV show. And off you go. Original sitcom. It's all going good. The TV show is going to be ground breaking, you write.

O'BRIEN: Right. MORGAN: It was going to resurrect the career of TV's Batman Adam West.

(LAUGHTER)

O'BRIEN: Sounds like a fool-proof plan, doesn't it?

MORGAN: Even as you're saying this --

O'BRIEN: Doesn't it?

MORGAN: I'm fearing the worse.

O'BRIEN: Yes.

MORGAN: It was going to be a comedy without a laugh track or a studio audience. It was going to change all the rules.

O'BRIEN: Yes.

MORGAN: And here's what happened. When the pilot aired, it was the second lowest rated television show of all time.

O'BRIEN: Yes.

MORGAN: It tied with the test pattern they show up in Nova Scotia.

(LAUGHTER)

O'BRIEN: Yes, true. True. But I've seen the test pattern and it's funny. It's a very funny test pattern.

MORGAN: So what are you thinking now? You've had this terrible disaster. Then you get a break. Then you get a little above yourself. Think it's easy. Then you get another disaster.

O'BRIEN: Yes.

MORGAN: What is going through your mind?

O'BRIEN: I think, you know, I'm Irish so we're just -- we always think that the worst is 10 minutes away or five minutes away. And so there's part of me that was always half expecting that. But yes, I think you constantly think it's over. I mean I've had that feeling of, well, I guess it's over about 35 times in my career. And one of them was just five minutes ago.

(LAUGHTER)

MORGAN: I mean is it the kind of career -- it always strikes me as odd that it's the kind of career comedy that attracts a lot of quite neurotic insecure people.

O'BRIEN: Yes. MORGAN: It's almost like the worst thing they should be going in for because that pressure -- like I said earlier, to make people laugh is like nothing on earth. I've done afternoon speaking.

O'BRIEN: Right.

MORGAN: And when a joke doesn't work and there's a terrible reaction, it feels awful.

O'BRIEN: Yes.

MORGAN: I can feel the sinew of my body starting to compress.

O'BRIEN: Yes.

MORGAN: I don't know how you guys do this.

O'BRIEN: Well, first of all, I've never experienced what you're talking about.

(LAUGHTER)

O'BRIEN: Every joke has worked, 35,000 of them. And they've all gone brilliantly. You know, what's interesting is that for me I'm one of those people that -- comedy is the release. Comedy is the -- doing comedy, although it can be scary and difficult, I find more agony in other things. You know what I mean? In -- if someone asked me to make them a sandwich, I would have more fear revolving around making that sandwich and insecurity than I would about doing comedy. So comedy in a strange way is the escape from --

MORGAN: Is there an art to comedy? People who have worked with you tell me that you have an incredible instinct for what is going to be funny. What I don't know is whether the instinct is what makes you laugh or your instinct is what you think will make an audience laugh.

O'BRIEN: I don't think --

MORGAN: Which is it?

O'BRIEN: I don't think about -- I just try and think about what I would have liked and --

MORGAN: What you would personally find --

O'BRIEN: What I would personally find funny. I don't know how to do it the other way. You make slight adjustments over the years. You learn this kind of thing probably wouldn't work for these reasons. But to me, there's a very strong -- comedy and music are very close together. And that's why musicians are always fascinated with comedy and want to be comedians. And comedians want to be musicians. Myself included.

We just -- there's something about having an ear for it. And the people I really like have a comedy ear. They just -- they have a sense. They have a sixth sense about what might work. And they go with that rather than trying to extrapolate what's the audience really going to like.

MORGAN: Your comedy took you to the chance to audition for the host of a new late-night show. Obviously the biggest break of your career. You debuted on the September 13th, 1993. You said, I was really, really happy. I thought I'd seized the moment. I'd put my very best put forward.

O'BRIEN: Right.

MORGAN: This is still the commencement speech.

O'BRIEN: Yes.

MORGAN: And that was when the most respected of widely-read television critic.

O'BRIEN: Right.

MORGAN: Tom Shales.

O'BRIEN: Right.

MORGAN: Wrote in "The Washington Post," quote, "O'Brien is a living collage of annoying nervous habits."

O'BRIEN: Right.

MORGAN: "He giggles and jiggles about. He fiddles with his cuffs. He has dark and beady little eyes like a rabbit. He's one of the whitest white men ever. O'Brien is a switch on a guest who won't leave. He's the host who should never have come. And let the late show with Conan O'Brien became the late, late show and may the host return to whence he came."

O'BRIEN: Yes. Yes.

MORGAN: And then you say, there's more but he gets kind of mean.

(LAUGHTER)

O'BRIEN: Yes. Yes. That was --

MORGAN: You get absolutely buried by the number one critic.

O'BRIEN: That was the nice part. That was the nice part, yes. And --

MORGAN: And when you read that, what did you feel?

O'BRIEN: I think a kind of weird elation? No. I'm --

(LAUGHTER)

O'BRIEN: I always respond inappropriately. You know, at the time, it's devastating, you know, to -- who can read something like that and not be devastated? I've never thought about my eyes the same way again. They are rotten beady like --

MORGAN: They are quite beady like.

O'BRIEN: Thank you. I'm having them completely redone.

(LAUGHTER)

O'BRIEN: They're going to be twice the size.

(LAUGHTER)

O'BRIEN: It's a very rare operation you can get. And I'll talk about it later. But I remembered, you know, at the time there was an intense amount of criticism. You think about it, replacing David Letterman at the height of his abilities. And I always said I was sort of like the great -- the greatest -- one of the greatest baseball players ever, Ted Williams, departing the field --

MORGAN: You haven't got to tell me about replacing TV legends.

O'BRIEN: Exactly, right. But like, you know, someone like Ted Williams leaving the field after a brilliant career and everybody going crazy and cheering and then them saying don't worry, his replacement's here, Chip Whitley.

(LAUGHTER)

O'BRIEN: And a guy like me running out. Hi, Chip Whitley here. Don't worry about Ted Williams. I'm going to catch up real soon. And then, you know, striking out right away. You can imagine what the reaction would be. So I never in my heart had any -- really had any ill will towards people because I think -- if I could have -- if I had not been myself and had watched Conan O'Brien debut after David Letterman, I'd have been horrified as well.

MORGAN: What you didn't know that day at Harvard, 2000, was of course you were going to land the holy grail of comedy.

O'BRIEN: Right.

MORGAN: "The Tonight Show."

O'BRIEN: Right.

MORGAN: And then you were going to have another down moment.

O'BRIEN: Oh, yes. And in a way, you know, I say I'm going to go on to have more, you know, bigger failures. I wrote that thinking, "not really."

(LAUGHTER)

MORGAN: Let's take a break. Because I want to hang on the big --

O'BRIEN: Yes. MORGAN: The big moment. Whatever you want to call it.

O'BRIEN: Right. Right.

MORGAN: Let's find out what you really think after the break.

(BEGIN VIDEO CLIP)

UNIDENTIFIED FEMALE: If you get hit by a softball?

O'BRIEN: Yes.

UNIDENTIFIED FEMALE: I don't get softball. It's soft ball but the ball is not soft at all. And if it hits you --

O'BRIEN: This is a "Seinfeld" routine. This is incredible. That was great. That was observational comedy. I'm going to get you in a comedy club tomorrow. You should do 10 minutes on this. It's really funny.

(END VIDEO CLIP)

(COMMERCIAL BREAK)

(BEGIN VIDEO CLIP)

DAVID LETTERMAN, HOST, "LATE SHOW WITH DAVID LETTERMAN": Forgive me for making this all about me but that's kind of what I do.

O'BRIEN: It's your show.

LETTERMAN: I was delighted by everything that happened. Except you losing your job. I --

O'BRIEN: I will tell you, I will tell you, and this is honest, the only consolation I took during that period was that you were happy.

LETTERMAN: You know, I refer to that period as the golden age of television, really.

O'BRIEN: The period when I lost the "Tonight Show."

LETTERMAN: Yes.

O'BRIEN: That brief week and a half period for you was the golden age of broadcasting.

LETTERMAN: Yes, that's right.

(END VIDEO CLIP)

MORGAN: Conan O'Brien on CBS' "Late Show with David Letterman." All laughing around then, but it's no secret that -- well, let's go to the moment you got "the Tonight Show." That moment is the holy grail of comedy in America. When you got it, is that how you felt? I mean, given all that had happened to you before, did you feel, this is it, I've got my 20 year plan now worked out for me?

O'BRIEN: Probably on some level, you think this is going to be fantastic. Then there's another level where they announced it. You know, it was this strange now clearly absurd plan that was announced, you know, five years ahead of time. Like one of Stalin's --

MORGAN: Yeah, quite extraordinary.

O'BRIEN: Stalin's grain production plans for the Soviet Union. Like, this will happen and, you know, that's just not how television works. In retrospect now, you realize it's a very -- it's a strange thing to have this weird handover --

MORGAN: As it crept nearer, that cutoff point.

O'BRIEN: Right.

MORGAN: And you can see that Leno's ratings were still pretty good and he's still number one, did you start to think, this is going to be tricky? Whatever happens, this is going to be an odd psychological thing? Because the guy leaving isn't leaving as a failure.

O'BRIEN: Right.

MORGAN: He's leaving because he has to contractually.

O'BRIEN: Well, the thing I'd say there, is no "Tonight Show" host has left. That was not the reason for any of them going. You know, Johnny -- I think the concept was at the network -- no one was expecting that to change. I certainly wasn't expecting that to change for Jay. I don't think that was necessarily the motivation. It was, you know, let's move on to the next generation.

MORGAN: So was that the greatest moment of your career, landing "the Tonight Show"?

O'BRIEN: Well, no, I don't think so. No, because I think obviously, in retrospect, there was this announcement and then it never, you know -- it never feel like it really did happen.

MORGAN: It took five years.

O'BRIEN: It took five years, and then was there for a few months. Then there was a plan to maybe shift this later and have him come back. It all seemed so silly. I'm honestly happier now, you know. I'm honestly -- this feels to me, now like a greater achievement for me, anyway, because I'm doing exactly the show I want to do. I'm doing it with people that I love.

And we get to do it our way. And we're with these amazing partners at Turner. So for me this actually feel feels like more of an achievement.

MORGAN: Also, this is where I guess all the catastrophes you had to endure in your earlier career, you could put it in some perspective. But actually you had always bounced back to something better.

O'BRIEN: Right.

MORGAN: Throughout your -- the pattern has always been something's gone wrong and then boom.

O'BRIEN: Yes. I think, you know, someone said to me -- I think it was my dad. Said if you read any biography -- my dad and I both love history. If you read any biography of a great figure, or a great historical figure, there's always -- if you cut to the middle of the book, there's always a lot of trouble. Like Churchill, there's lots of disappointment.

Not that I'm a great figure, whatever, would be. But there should be -- in a good career, there should be a lot of challenges. And so I wouldn't -- I would honestly not really change anything that happened. It's been fascinating. It brought me to where I am now, which I love.

MORGAN: What did your parents say to you when it ended?

O'BRIEN: They don't follow the news. They think I'm still hosting "the Tonight Show." They think I'm doing a lovely job. They're very confused.

MORGAN: Do you feel more free, more liberated?

O'BRIEN: Yeah, definitely.

MORGAN: It seems to me --

O'BRIEN: They let me do whatever they want.

MORGAN: You have a lot of autonomy, don't you?

O'BRIEN: Yeah, you know, we -- we are partnered with Turner on this. And it's a fantastic opportunity to -- first of all, they encourage us to travel the show constantly. We've already been to New York and Chicago. We've traveled twice in one year, which is unheard of for these shows. They've also really -- they've been amazing partners in helping us build what I think is a new kind of talk show, where we have an incredible social network presence and we're also able to have this show that's very -- I think a very funny show, but also a show that is having a dialogue with our audience.

We're actually talking to our audience. They can talk back to us through the social network. They can sometimes affect what happens on the show. In that way, I think it's been really thrilling creatively for the last two years.

MORGAN: Let's take another break. I want to come back and talk about some your greatest hits as a talk show host. It's going to be an unrelentingly positive segment. No more humiliations, no more failures, no more rising from the ashes. Pure glory.

O'BRIEN: Wow, let's get to that. That will be nice. (COMMERCIAL BREAK)

(BEGIN VIDEO CLIP)

(SINGING)

O'BRIEN: Let's hear the instrumental part.

My skills are really amazing.

Snuck into the room to see what --

UNIDENTIFIED FEMALE: Snuck isn't a word, Conan. You went to Harvard and you should know that.

O'BRIEN: Snuck. Past and past part of sneak.

CHRIS FARLEY, COMEDIAN: Look at me, I'm on Conan O'Brien, with my feet up on the desk and phone in the show. Well by God, I got a couple words for you. You better get your act together!

(END VIDEO CLIP)

MORGAN: Some of your greatest hits there from "the Late Show." When you look back over, you've done thousands of interviews now and thousands of monologues. But if I gave you, right, you've got five minutes left to live, you can relive any moment from any of those shows.

O'BRIEN: So this is the positive part of the interview? Five minutes left to live.

MORGAN: You've got five minutes left to live.

O'BRIEN: Fantastic.

MORGAN: What would you go for?

O'BRIEN: Which guest would I go for?

MORGAN: Or a moment or something where you really thought it defined you or was just, for whatever reason, particularly memorable.

O'BRIEN: Wow. OK. I did a -- I did a very silly remote once where I -- we found a group of baseball players that play baseball in late 19th century rules. And they do it in the costume with the mustaches. So I went out and put on the mustache and spoke in that sort of turn of century baseball. It was so me. I've always said whenever I go, don't even give a eulogy, just show that piece.

It only lasted a few minutes, but it's me with the big mustache and acting like a complete ass. That's my favorite thing to do. It was right in my wheelhouse, so to speak. Very silly, but also had these great magical moments in it. So I would say roll that.

(BEGIN VIDEO CLIP) O'BRIEN: Hurl that apple, hurler. If that was any lower, I'd have to dig to Hades itself to find the apple. Why not dig a trench, then the ball would be as low as you seem to wish it to be.

That was no strike.

One more of those and you'll regret it, see. What is that demonry?

Everyone's free.

(END VIDEO CLIP)

MORGAN: In terms of guests, who are the ones that when you see they're coming back, your eyes light up because you think, OK, this is going to be great?

O'BRIEN: Tom Hanks is one of the great guests of all time. He's just the whole package. He is a massive superstar who also is as funny as any comedy writer or comedian that I've ever known, and also knows how to tell a story. He's a raconteur. They didn't exist anymore, people like that.

MORGAN: What is the nightmare guest for you, generically?

O'BRIEN: I would say you're awful, dreadful.

MORGAN: Why do you keep having me back?

O'BRIEN: You always find your way in. We don't even invite you. Half the time, they just pull out to a two shot and Piers is sitting there.

MORGAN: You did a funny one recently with the Romney sons.

O'BRIEN: Yes.

MORGAN: Let's have a look at this.

(BEGIN VIDEO CLIP)

O'BRIEN: A large family to me, but this is just the tip of the iceberg. We have a photo here of a family gathering of the Romneys. Absolutely incredible. When you guys get together, there's a global khaki shortage. There's a panic worldwide.

(END VIDEO CLIP)

MORGAN: How comedically rich has this campaign been for you?

O'BRIEN: It's funny because our show doesn't focus on politics as some of the other shows that do it really brilliantly. We touch on it when it works for us. Sometimes my show can be shockingly irrelevant to the news. We also do that. I find sometimes probably people tune in to us when they want to escape what's happening in the news, because we have the ability sometimes to just create our own comedic world and live off of it.

But obviously it's something that is a source of humor. And you know, so you figure it out and it -- it got much better for us once it was decided it was Obama versus Romney. For a while, sorting it out, it gets so complicated that you've got so many different comedic angles going, that I think once it settled into Romney versus Obama, it doesn't matter if you're on the left or the right, if we can find a way, to me, that's the only hope. That's the common ground, is if we can together come together and mock "Jersey Shore," then we've really -- we've brought this country together.

MORGAN: Of course you met your wife on a comedy show.

O'BRIEN: Yes. Yes, I -- well, I met her when I was working on the late night show. And I went out in the field to shoot a remote. I went to an advertising agency and she was one of the ad executives.

MORGAN: We're going to take a short break and come back and talk about your wife, the comedic rock. Want to know who makes who laugh most.

O'BRIEN: Interesting.

MORGAN: Whether you laugh in bed. Whether she laughs at you in bed.

O'BRIEN: Doing very badly.

(BEGIN VIDEO CLIP)

CROWD: Three, two, one, go.

O'BRIEN: Yes.

(END VIDEO CLIP)

(COMMERCIAL BREAK)

(BEGIN VIDEO CLIP)

(SINGING)

(END VIDEO CLIP)

MORGAN: The classic Marge versus the monorail "Simpson's" episode, voted fourth best of all-time. Are you pleased? Are you pissed off you're not in the top three?

O'BRIEN: Enraged. No. I'm just -- you know, the Simpson for me is a gift that keeps giving, because I'm always very clear with people. I didn't create that show. I did nothing -- that show was up and running and a massive success when they let me step on board for a few seasons, just before I took over the late night show.

And so I loved it. I absolutely loved it. What's nice is that those episodes are out. They're always bouncing around. I can be anywhere in the world and people will occasionally, in any other country, bring up one of the episodes that I worked on. In that way, it's this beautiful gift that keeps giving, yeah.

MORGAN: Let's talk love, romance, marriage. How many times --

O'BRIEN: Well, which one?

MORGAN: Let's start with love. How many times have you been properly in love in your life?

O'BRIEN: As you know, I'm married. So there is one answer to that. That is once.

MORGAN: Is that the diplomatic answer?

O'BRIEN: I would say properly in love, yes, my wife Liza.

MORGAN: You've never had your heart broken before that?

O'BRIEN: It wasn't a woman. It was a cat that betrayed me. We don't want to talk about the animals. Yes, I would say I -- I'm going to go with my answer, my wife. my beautiful wife. She's my only true love.

MORGAN: When did you realize she was the one?

O'BRIEN: Instantly.

MORGAN: Was it instantly?

O'BRIEN: I'm just giving you the answers that are going to make it all OK for me. Don't screw with this, OK? Instantly, I knew right away. Yeah, actually I did know very quickly. We were -- it was being shot for television, so somewhere in the vault at NBC there's footage of me literally falling for my wife on camera. It's --

MORGAN: What was it about her?

O'BRIEN: She -- well, to be crass, she's incredibly beautiful. So that was the first attention getter. And I'll admit that does work occasionally on a guy. Ladies, little trick for you. When you're really beautiful, that can work sometimes. And then what was nice is that we just talked on the phone for a while. That was our relationship, because I'm impotent.

Is any of this going to get in the papers, do you think? This won't get out. So we -- we -- but we did talk on the phone for a while, and she's very intelligent and funny, and a really good person. So the nice thing is that that was the basis of the relationship. So I just knew.

MORGAN: Are you a romantic man?

O'BRIEN: I'm going to say I have -- deep, deep down, under layers and layers of repression and ham, and layers of carbohydrates, there's a romantic guy down there, yes. But man is that covered up. It's a Slim Jim of romance with massive insulation layers of insecurity and self-loathing wrapped around it.

MORGAN: How would you like to be remembered?

O'BRIEN: That guy was well endowed. Massive. Just he was a freak show. I saw him in a men's room. It was scary. That's the kind of -- no, honestly I would -- if anyone remembers me at all for any amount of time, I would like to be thought of as someone who -- I do try, I think, sincerely to be nice to people and try to make them laugh. And I think mostly it comes from a good place, so that would be with nice.

If not that, the hair, I'd like to be known for. And then the endowed thing would be great, if we could just slip that in. Like just --

MORGAN: So you make people laugh, you're well endowed and you have ginger hair.

O'BRIEN: Yes.

MORGAN: That's not a bad triumvirate to be remembered by.

MORGAN: I think in a way, and the fact that you've just verified it as a journalist, those three are all true. And you would know. You've seen me. We with often go to the spa together.

MORGAN: Not now here, come on.

O'BRIEN: It was your idea.

MORGAN: That is a terrible idea. This is really uncomfortable. It is uncomfortable.

O'BRIEN: It was your spa. Turns out it's not even a spa. It's a room. It's a creepy room he has.

MORGAN: You're not going to get your plug if this goes on.

O'BRIEN: Oh, yeah. Do the plug.

MORGAN: You want to read it?

O'BRIEN: Sure. Watch this. Where's my camera? One? Watch Conan week nights at 11:00 Eastern, 10:00 p.m. Central on TBS. Miss it and you're a fool. We'll take a break. When we come back, Madeleine Albright will be here. She's going to make cookies with us.

Also, Angela Merkel coming up next. You talk to real human -- real people that have done real things. What was this?

MORGAN: I loved it.

O'BRIEN: We had a good time. Nice talking to you.

MORGAN: Conan O'Brien. When we come back, Only in America. Talk about a photo finish. Why this race may come down to a toss of a coin.

(COMMERCIAL BREAK)

MORGAN: For tonight's Only in America, a real photo finish. Take a look at this, Alison Felix and Jennifer Tarmo (ph) crossing the finish line in the women's 100 meters at the U.S. Olympic track and field trials on Saturday. Jennifer is wearing number one, Alison wearing number two. As you can see, they finished in a dead heat for third place and for the final coveted spot on the women's 100 meter Olympic team.

To give you some idea what it means to them to make it London, listen to what Alison Felix told me when we sat down recently?

(BEGIN VIDEO CLIP)

ALISON FELIX, 100 METER RUNNER: I've got to win. That's what it's all about. like you said, I've done all this other stuff, but this is the one missing thing, and it's the thing I really want. I need everything to come together at the right time.

(END VIDEO CLIP)

MORGAN: Well, it came together all right. Unfortunately, just as Jennifer Tarmo's came together as well. In the first instance of its kind, they were both given the exact same time, down to thousands of a second, 11.068 seconds. After all that grueling training, after running their hearts out in a race to get that last spot on the team, Alison and Jennifer now have two choices, a runoff or a coin toss.

Not just any old coin toss, there are some seriously pedantic rules for this kind of thing. And they are as follows, quote, "the USATF representative shall bend his or her index finger at a 90 degree angle to his or her thumb, allowing the coin to rest on his or her thumb. In one single action, USATF representative shall toss the coin into the air, allowing the coin to fall to the air."

What a complete joke. This is no way to decide this epic tie breaker. Ladies, you were born to run, so run again for greatest prize of all, to represent your country in the Olympics in London. And may the best woman win.

That's all for us tonight. "AC 360" starts now.