don't screw with this, okay? >> 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 and arthur of what's been voted the fourth funniest simpsons episode of all time. >> thank you so much. you didn't even scratch the surface. i have a high fall setto. i sing like an angel. i'm hairless. there's many things. i'm aerodynamic. there's nothing i can't do. >> what is the genuinely weirdest thing about you that nobody knows? >> wow, that's a good one. the weirdest thing about me that nobody knows. i can be amusing at times. seems to have escaped people's notice. >> you don't do many interviews. >> i don't do a lot. >> i've been trying to lure you for like 18 months. i've appear on your show endlessly in a desperate attempt to lure you in. >> 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 way, to be on television. and no one in america seems to want me to be on more. so i -- if anything, pull it back. but i couldn't resist this. you have this beautiful lucite desk. it's very nice. it's like a classy airport lounge. it's beautiful. but i'm thrilled to be here. >> i'm thrilled you're here. i'm a huge fan, as you know. take me back to the first moment you made somebody laugh. do you remember it? >> yes, it was about four years ago. i remember it very well. it was my wife. we'd been married at that point for seven years. let's see. i don't remember the exact moment. my mother claims 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. i think it always starts with the family. 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 togethering. >> where do you come in the pecking order of the kids? >> we're not sure. we're always finding new ones. i walk into the bathroom and -- i'm liam. oh, we don't think we met. 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. >> what do they make of being related so closely to the coco phenomenon? >> i think it's -- my brother, luke, looks a lot like me. luke and i look very similar. and we're only about a year apart. he lives in boston. 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. anyway, he said he was walking people will follow him and follow him into a store and he has to turn and say no, i'm not him. he is actually. luke's a genius. >> your family, very close family. >> we're still close. intalk to someone in my family at least every day. what's great about my family is they don't care that i'm on television. they don't care. they -- 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. they love to do that. they love to do that. >> which is not -- it's not a very common thing in american psyche to take the piss as we call it. sarcasm isn't a massively advanced part of the american humor. >> it is in different parts. it depends 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 what i love about boston. this is a true story. i showed up in boston once a couple months ago. and i landed at logan airport. and i get out and there's a cab line. 'cause i'm gonna take a cab to my parent's house. so i'm headed towards the cab line. long before i even get a chance to get to the back the cab line, this guy sees me coming. and he just -- he's the guy that runs the cab line. he goes, hey, back of the line, tv star. and i said, i was headed to the back -- yeah, you're like the rest us now, pal, you know. that's where i was headed. but they don't even give you the chance. it's they need to take you down a notch right away. >> when you were young, apparently in the third grade -- >> when i was younger. >> younger, my apologies. >> i'm 26. >> even in third grade, you did charlie chaplin impressions. >> yeah, yeah. >> you said to your parents as a kid, mom and dad, i'm going to be in show business, i need to learn who tap dance. >> yeah, true story. >> i love that line. >> television in those days very different from tv now. in the 1970s, they -- there's only a couple of channels. and the uhf stations, channel 3 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 -- >> what was it, gene kelly, fred astaire? >> yeah, i was watching old gangster movies. humphrey bogart films. the movie "that's entertainment" came out. showing you what entertainment is. i thought like an idiot in the 1970s thought that was what entertainers needed to have to know. gene kelly. you have to know how to sing, dance, move. know how to do it all. i marched up to my parents and i said, i need to know how to tap dance. they thought all kinds of things. but they said okay. 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 bo jengles robinson. he lives in this -- worked out of this delap talted 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. 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. then he would work with me. so my parents, god bless them, they were great that way. my dad's a my crow biologist and a scientist. my dad's a lawyer. they said this is what he wants to do. >> have they ever regretted helping you get into show business? >> i think no. i'm sure they have since. >> your mom in particular. my mother when it's going great, it's fantastic. when things aren't going well. it's so high profile and you get hammered. they feel it personally. >> 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. i said, by the way, you should know, i'm a hired assassin. we don't care. kill who you need to kill. >> show business was part of the allure of it being famous if you're honest, when you look back to that time? >> i have to say -- this is true of a lot of comedians. 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. there is something initially especially in those early days. you notice -- you go through the check list of your mind of what do i have that might interest a girl. and i didn't have much. inwould 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 -- >> just to get girls? >> not even -- not just get them. to get them to look in my direction, piers. i'm taking it down to a much more basic level. you know. >> you moved to l.a. after harvard. come to your harvard commencement speeches in 2000. one of the classic commencement speeches. >> have they ranked the commencement speeches? i'm very competitive. >> you've got to be number one. you're fourth on the list of simpsons episodes. >> that i can accept. >> when you went through harvard, everything much have seemed like it was all going swimmingly. you've got no agony, no torment, no pain. your father wasn't stubbing cigarettes in your face. >> that's the dumbest thing anyone's ever said to me, piers. yes, tons of agony. it's very hard to look at someone's life in the abstract -- >> where was your agony? >> 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. 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. i think that is the common denominator you see with a lot of people. artists or performers. they don't think they belong. >> you still feel it? >> yes, i feel it today. i, i wasn't sure they'd let me in here. there's a constant -- >> is there pressure to be funny? that must be very particular -- >> it's funny, the -- it's odd or ironic, whatever you want to call it. my desire -- getting into comedy was a very beautiful accident. because i worked very hard at everything. i tried really hard. comedy was something i stumbled into when i was in college. i wanted to be a performer. and then thought, this isn't going to happen. i'm from brookline, massachusetts. may parents said, we don't know anybody in show business. 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 i was meant to do. i loved it. i absolutely loved it. 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 it has some cachet in the real world. and these older students really seem to like the stuff i'm writing. and they seem to think i'm funny. 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. >> so harvard. >> yeah. >> making people laugh. everything's going great. let's take a short break because after the break it all goes horribly wrong. >> sex change. sex change when we return. >> i didn't want to mention it first. >> i was a girl. i was a boy. as a doctor, i do everything i can to make sure my patients get the very best care. but look at our health care system. everyone agreed we needed reforms -- but this new health care law -- it just isn't fixing things. president obama promised my patients that they could keep me -- but what if because of this new health care law -- i can't keep them? i've looked at this law. i know the consequences: delayed care and worse yet -- denied care. studies show the president's health care law is projected to add hundreds of billions of dollars to our deficit -- and increase spending by more than a trillion dollars. and the truth is -- we still don't know how much this law will eventually cost. i don't want anything to come between my patients and me -- especially washington bureaucrats. we need real reform that improves care, and the president's health care law just isn't it. it just isn't worth it. this is where health care decisions should be made. not in washington. when it comes to home insurance, surprises can be a little scary. and a little costly. that's why the best agents present their clients with a lot of options. because when it comes to what's covered and what's not, nobody likes surprises. [ click ] [ chuckles ] we totally thought -- [ all scream ] obscure space junk falling from the sky? we cover that. moving on. aah, aah, aah, aah. [ male announcer ] we are insurance. ♪ we are farmers ♪ bum, ba-da-bum, bum, bum, bum ♪ i took a lot of criticism. some of it deserved. i'll be honest with you, it hurt like you would not believe. 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. my mistakes have been necessary -- >> you wrote this incredible commencement speech at harvard year 2000. i want to sort of tell the story of what happened to you after you left harvard through the prism of the speech. 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 move to los angeles. i got a apartment. i bought a car. you said it was a car -- >> the isuzu. >> they only manufactured for a year because they found out technically it was not a car. >> i don't know what it was. it was a hair brush more than it was a car. >> but you go work on a show for a year. you must be thinking, i'm a harvard graduate, i've got on the show, life is beautiful. >> i'd love to pretend that's what i thought. 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 lost that job. and then a lot of series of misadventures and highs and lows. >> at one stage, you're sent to the wilsons house of suede and leather and you're sitting there thinking how did a harvard graduate end up here. >> yeah. i had those thoughts many times. 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. >> because all around you are success stories. >> yes. >> billboards and -- the whole machinery of the city is geared to achievement, success. not failure. >> right. >> 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. >> on this town, when you walk on a sidewalk, you're perceived as a failure. what happens -- >> if you walk you're peer perceived as a failure. >> 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. i guess he's, you know -- it's not like new york or any other city in that way. you just -- so yeah that was a very -- there's lots of intense kind of despair. >> you then get a big break. "saturday night live." >> i believe this gentleman has something to say. >> i just completed your course. i never dreamed i could be this handsome. thanks. >> you're handsome. give that man a round of applause. >> and after a year and a half, they read your sketches, they give you a two-week tryout. the two weeks turns to two seasons. you think, i made it. you get so cocky, you think, i'm going to go and write my own tv show. original sitcom. it's all going good. the tv show is going to be ground breaking. it was going to resurrect the career of tv's batman adam west. >> sounds like a fool-proof fan, doesn't it? >> i'm fearing the worse. a comedy without a laugh track or a studio audience. it was going to change all the rules. when the pilot aired, it was the second lowest rated television show of all time. it tied with the test pattern they show up in nova scotia. >> yes, true. true. but i've seen the test pattern and it's funny. it's a very funny test pattern. >> what are you thinking now? you have this terrible disaster. then you get a break. then you get a little above yourself. think it's easy. then another disaster. >> i think, you know, i'm irish so we're just -- we always think the worst is ten minutes away or five minutes away. and so there's part of me that was always half expecting that. but yeah, i think you constantly think it's over. 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. >> is it the kind of career -- the kind of career comedy that attracts neurotic insecure people. it's almost like the worst thing they should be going in for. that pressure to make people laugh is like nothing on earth. i've done speaking. when a joke doesn't work and there's a terrible reaction, it feels awful. i can feel the sinew of my body starting to compress. i don't know how you guys do this. >> well, first of all, never experienced what you're talking about. 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? 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. comedy in a strange way is the escape from -- >> is there an art to comedy? people who have worked with you tell me 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. >> i don't think about -- i just try and think about what i would like. >> what you would personally -- >> what i would personally find funny. i don't know how to do it the other way. you make slight adjustments. you learn this kind of thing. probably wouldn't work for these reasons. to me, there's a very strong comedy and music are very close together. and that's why musicians are very fascinated with comedy and want to be comedians. and comedians want to be musicians. myself included. there's something about having an ear for it. the people i really like have a comedy ear. they have a sense. they have a sixth sense about what might work. they go with that rather than trying to extrapolate what's the audience really going to like. >> a chance to audition for the host of a new late-night show. biggest break of your career. you said, i was really, really happy. i thought i'd seized the moment. this is still the commencement speech. wrote in "the washington post," quote, o'brien is collage of annoying habits. he has dark and beady little eyes like a rabbit. he's one of the whitest white men ever. 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 where he came. there's more -- you get absolutely buried by the number one critic. >> that was the nice part, yeah. >> when you read that, what did you feel? >> i think a kind of weird elation. no. i always respond inappropriately. 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 beady like. >> they are beady like. >> i'm having them completely redone. they're going to be twice the size. it's a very rare operation you can get. 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. i always said i was sort of like one of the greatest baseball players ever, ted williams, departing the field -- >> telling me about replacing tv legends. >> exactly, right. someone like ted williams leaving the field after a brilliant career and everybody going crazy and cheering them saying don't worry, his replacement's