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Conan O'Brien On Late-Night TV: 'All I Ever Wanted To Do Was Make People Laugh'


This is FRESH AIR. I'm Terry Gross. I hope you're enjoying your Thanksgiving. We're going to spend our FRESH AIR Thanksgiving in the very good company of Conan O'Brien. Last week, he announced he'll be ending his late-night show in June after 28 years of hosting daily late-night shows. The last 10 years, his show was on TBS.

One of his new projects will be hosting a weekly variety show on HBO Max. Conan O'Brien will continue to run his multimedia company, Team Coco. Conan started his career as a comedy writer for "The Simpsons" and "Saturday Night Live." When he first started hosting NBC's "Late Night With Conan O'Brien" in the spot that had been David Letterman's, he was an unknown as a performer. A lot of people thought he wouldn't make it. But he's hosted late-night shows longer than anyone.

His career has taken some surprising twists and turns, which we talked about when we recorded this interview last year in October. He was making changes then, too. Season 2 of his podcast, "Conan O'Brien Needs A Friend," was about to start. He was cutting back his hour-long late-night show to a half hour. And his production company, Team Coco, was launching new projects.


GROSS: Conan O'Brien, welcome back to FRESH AIR. It's been a long time. And it's a great pleasure to have you back.

You're kind of shaking things up in your life. I mean, you've changed your hour TBS TV show into a half hour. And you're doing all these new podcast ventures and doing stand-up comedy. And now you have this series of performances at clubs around the country kind of produced by Team Coco. So what's going on in your life that made you want to make all these changes?

CONAN O'BRIEN: I'm having a nervous breakdown.

GROSS: I knew it. I knew if I asked, you would tell me that. Thank you.

O'BRIEN: (Laughter) Yeah. No. If I am, it's a very...

GROSS: I ask the questions that get the deep answers

O'BRIEN: Yes. Yes. It's the Larry King method.


O'BRIEN: Larry King used to - I famously said once (imitating Larry King) I don't prepare for interviews. I just ask whatever pops into my head. That's my technique.

And I said, that's not a technique.


O'BRIEN: That's just called - that's just called not preparing, Larry. (Imitating Larry King) That's my technique is I just get up and I eat a giant ham sandwich and then I go in and I say whatever happens and then that's my magic.

But, you know, I decided a little while ago - I've loved my career. I've been very lucky. I am hard-pressed to think of something I wanted I didn't get to do. And so - you know, and I'm very lucky in my personal life. I married the right person. I have great kids. So at a certain point, you say why not? There's so much fear and intensity in my teens, 20s, 30s, into the 40s. It was so much intensity and iron will and I will work really hard and I must - this has to be fantastic, and this has to be great, and this needs to be better that I think something happens. You know, a doctor would say, oh, yeah, your testosterone is dropping. You're getting older. They would have some chemical reason, and it might be right. I don't think I ever had a lot of testosterone, and what I've had has probably been cut in half. I'm now - I think genetically now I'm a Belgian woman, but I often get people stopping me on the street and saying you are a very attractive woman (laughter) clearly from the Netherlands, and you're very tall. And I thank them, and we meet for coffee, and then I move on.

But I guess I got to a phase where I thought I don't - what I don't want to do is sleepwalk my way through my career at this stage. I think it be very easy to - OK, I got this down. I can do this for a bunch of years (ph) and then, you know, sort of fade off into the sunlight. And I thought that's - or there's another way to go, which is scare yourself and try to be - rather than be intimidated and afraid as a lot of middle-aged people are by everything that's changing, choose to be excited by it. You know, maybe some later career cookiness (ph) doesn't make any difference. You know, if people don't like it, they don't like it.

GROSS: Do you think the things that you find funny or the comedy that you want to do has been changing as you get older?

O'BRIEN: Yeah, probably. Well, I don't think the things that I find funny have changed. I still find the same things funny. And I really love the silly and the silliness and the absurdity that I can find in everyday life. I think as time goes on, I've become much more interested in things that - and, actually, this has probably always been the case, so I don't know if I can say it's new. But my interest in what we call evergreen comedy - comedy that - think of a Warner Brothers cartoon. You can watch it today, and it was - maybe it was made in 1948. You know, whether it's Bugs Bunny or Coyote Road Runner, you're watching one. And it's just the timing and the simplicity of the ideas but the beauty of the execution. It's - all is funny today as it was when it was shown in a theater in 1948.

But I like comedy that is about me as a person who's somewhat ridiculous going through life and whether it's Chaplin-esque or Jacques Tati or it's just - it's about a person encountering - being embarrassed or humiliated or being - you know, going through life and sort of like Buster Keaton or any of those great people. I'm not playing at their level, but I - that is my approach to comedy is to try and find connections and things that other people can relate to. And those are the things - some of these remotes that I've shot over the years are my - probably my favorite medium in all of comedy is I have this - you know, hundreds and hundreds of these remotes I've shot. And some of them, I think I really managed to make something that might be a little bit timeless. And that's the stuff I'm in love with.

GROSS: So are there jokes that you feel like you can't tell anymore in this era of heightened feminist awareness and the #MeToo movement? Like, one of the things you always used to do was, like, your Bob Hope growl at attractive women. I mean, you went really...

O'BRIEN: Yeah (growling).

GROSS: Yeah. That - I mean, that was...

O'BRIEN: No. You know what? I still...

GROSS: And you'd massage your nipples...

O'BRIEN: I didn't let go of...

GROSS: ...As part of the joke. Can you do that anymore?

O'BRIEN: Yes. Well, first of all, I always molested myself...


O'BRIEN: ...Which I think we're still allowed to do.


O'BRIEN: The other thing is the growl, you know - I would - when women would come on, it was this cartoony Bob Hope thing of (growling). And I don't know if anybody has ever seen it as sexual because I don't know that I come across as - (laughter) I'm being really bluntly honest - as that sexual. And so I don't know that I do the growl as much anymore. But I find that the response is usually women laughing at me because it is such a caricature of a guy - a cartoonish, non-sexual person attempting, you know, this crazy what is sort of 1950s or 1940s tiger growl. So, yeah, I don't know that that is - the tiger growl is - I don't know if that's verboten in - because I don't know that anyone takes it seriously, nor should they. But...

GROSS: No, no, agreed.

O'BRIEN: I'd hate to lose it completely.

GROSS: Right, right.

We're listening back to the interview I recorded last year with Conan O'Brien. We'll hear more after a break. This is FRESH AIR.


GROSS: This is FRESH AIR. Let's get back to the interview I recorded in October of last year with Conan O'Brien. Last week, he announced that he'll end his late-night TBS show in June and then host a new weekly variety show on HBO Max.


GROSS: You've had the strangest career of all the late-night hosts. You'd been more of a writer than performer when you got your 12:30 late-night show on NBC, coming on right after "The Tonight Show." No one knew who you were, and it took a while for you to catch on. When Leno left "The Tonight Show," you replaced him. Leno got a 10 o'clock show that didn't do well. He wanted to go back to the 11:30 spot, and NBC let him do it. So before your year was up, you were out of the 11:30 spot. They offered you a spot at 12:05 to do "The Tonight Show." And you basically said, that's ridiculous. And you left and, you know, a few months later, started your show on TBS. So your career has had this strange mix of, like, complete stardom and rejection mixed in. And I just think psychologically, that must really be like a roller coaster.

O'BRIEN: Yeah. That was - first of all, just listening to you summarize it right now, I went through seven episodes of PTSD...

GROSS: (Laughter).

O'BRIEN: ...Just listening to your - just listening to the summary of what I already know happened, I'm just - I'm completely drenched. I'm drenched in sweat right now, in need of medication, which I'm taking. Here we go and done.

Yeah, it's - I have to say, I agree with you. It has been - say what you want about my career - you can - someone can like me, they can despise me, they can completely not care (laughter) be completely neutral about me, but everyone would have to agree that it's a really unusual career, just completely unprecedented. I mean, the way that I got onto the "Late Night" show was absurd, which was basically they - Lorne Michaels took a complete Hail Mary pass and said, I know this writer, and he has, you know, very little performing experience besides some improv, but I think he could be good. And I went to an audition and, because I had no chance, was completely relaxed in the audition and did really well. And then NBC said, well, we have no other choice (laughter) because this is pre - I mean, it wouldn't happen today.

Today, if there was a major "Late Night" spot open, there would be 600 candidates from 600 different cable shows. So the whole way I got the show was absurd, hanging on to it for the first year, year and a half, two years, when I think I was actually canceled at one point in a meeting. And then shortly after the meeting ended, they said, well, we can't cancel him yet because we don't have his replacement quite ready to go. So let's uncancel him and then cancel him at the next meeting. And then they just didn't get around to it.

So I was supposed to die about six different times and just didn't through some - I don't know what else to call it other than dumb luck. And then, yeah, you push forward through all these years of success to - it's like being a college professor - you're getting tenure. You're going to get "The Tonight Show." And people don't - they don't try you out at "The Tonight Show." They give it to you and then...

GROSS: Then they take it away (laughter).

O'BRIEN: ...My predecessor it had - yeah. And then my, you know, my predecessor had had, you know, some difficult times. It all worked out. So the feeling was - at that point, I'd been on the air for 16 years and, well, this should be OK. And then it was - as he said, it was just this crazy set of circumstances. And that was traumatic. And I did a tour, which was very therapeutic. I went out on the road, and I did comedy and some music. And it was just a big variety show. And we had a lot of insanely huge guest stars come out in support.

GROSS: Was it helpful to you to have audiences who were incredibly enthusiastic about seeing you at this time when you'd been rejected from NBC?

O'BRIEN: Yeah. Oh, it was - it was therapeutic and satisfying to - you know, all I ever wanted to do was make people laugh. I know that sounds corny. The motivator, to me, is I just really do love getting in front of people and making them happy, making them laugh. And so getting to do that on a national tour and really delighting these crowds, that was great.

I think the trouble, for me, came after that tour because I think I emotionally crashed. You know, the tour - it's, like, probably a typically Irish response. But you'll do - the Irish, a lot of times, will do anything to avoid feeling pain. So I think it was very - obviously, very painful to have to give up "The Tonight Show." And so what I did was I avoided that pain by doing this tour where I probably burned 3,000 calories a night, would sweat through my clothes, really give everything I have, then go out and take selfies with a thousand people, then sleep for a couple of hours, but then not be able to sleep on the bus and on the plane and just - I think when that tour was over, I was skeletal. And then I was faced with - we got to start over again, build a new show. And I think that was the painful part. That was the part that took a good two years to work through.

GROSS: What helped you through it?

O'BRIEN: Well, I like being honest about this for other people out there. I had always done some therapy, but I went to - I got a lot of therapy, and I got some help with medication. And that helped a lot. And then it also helped a lot that, as I said earlier, the smartest thing I ever did in my life was marry my wife in 2002. So it's been 17 years, and she's just a great partner and very emotionally intelligent and my best friend. And so she helped me through this. And you have kids, too. I mean, I have two children, so that puts things in perspective.

GROSS: Mmm hmm.

O'BRIEN: So all those things helped me enormously. And, you know, I've since become a big advocate for people who are - if they're going through something and they're having a hard time - you know, talking to somebody and getting some professional help. I remember when I was a guest on your late-night show on NBC back in, I think, like 2004, when the show was - I was, like, the last guest. And when the show was over and you were leaving the set, you were very generous with your time. You spent a few minutes talking with me. And I introduced my husband to you. He's a big fan. And you said - you said, wow, now that the show is over, I can go back to being depressed. And it was really funny. But at the same time, I thought, I bet there's some truth to that, too, that once you leave the stage, like, depression takes over.

O'BRIEN: Yeah. You know, it's funny. Everyone has a different - I used to think I'm not depressed; I'm just anxious. And I didn't understand. But I've always been - I was anxious as a little kid. I think I started having real bouts of strong anxiety around - in fourth grade, I remembered - fourth, fifth, sixth, seventh, I mean, through high school. And I was - just had a lot of anxiety and anxiety in the night and getting up a lot and not understanding what it was.

And so I remember there was a period in my life in my 40s when people were saying, you know, maybe you're depressed. And I would be irritated. I would say, I'm not depressed. I have anxiety, but I'm not depressed. And then, of course, when I finally went and got some help, you know, at this sort of big, chaotic time in my life, one of the first things that the doctor said to me was - I said I'm not depressed. I'm - I just have anxiety. And they said, you know, yeah, anxiety is a - chronic anxiety is a - it's a subset or form of depression. It's a mode, you know?

And so I think because I was able to function so well - I can always work, I can always get up and do what has to be done - and I just thought, well, I'm not depressed. And I had read accounts of people with real depression who can't get out of bed. And I said, that's never been me. And so I'm not that, so I don't have depression. But I realized that anxiety is a form. It's certainly something that can get in the way of your life. And yeah, I did go down - it's sort of a classic trope, but I think there's a lot of truth to it, which is when you're a performer, when you're on stage, there's no thinking. You just have to act. There's no time to think. You just do. And so for that time that you're in front of people, in a weird, crazy way, you'd think that the anxiety would be at its peak. And it's not. Everything goes away because there's no time. You're just in front of them. And you just react. And you completely rely on your muscle memory and your inner clown that's been there since you were born. And you just go. And it's very liberating, and it's really freeing.

The problem is when it's over and you need to negotiate - then you have to start thinking again about, well, what's tomorrow? And what are we going to do? And then it's all back in your brain, you know? It's not you just sort of reacting out of your diaphragm or your soul or whatever. You're back in your brain. And that's where the problems start. So when I say it's time to be depressed again after a show, it's much better now. I mean, now I go home, and I see my wife and kids and deal with whatever they're dealing with. And - so it's different. And, you know, it's not it's not the way it used to be. I used to go home and brood about, what am I going to do next? And what's tomorrow? And how was that show? And if it was a good show, can we replicate it tomorrow? If it was a bad show, oh, my God, how are we going to make up for that? What will people think? There's less of that now. So it's - it was a joke, but it wasn't a joke.

GROSS: We're listening to the interview I recorded last year with Conan O'Brien. We'll hear more after we take a short break. And jazz critic Kevin Whitehead will review Sonny Rollins' studio and live recordings from 1967 that have just been released for the first time. I'm Terry Gross, and this is FRESH AIR.


GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with Conan O'Brien, which we recorded in October 2019. Last week, he announced that he's going to end his late-night TBS show in June after 28 years of hosting late-night shows, which is longer than anyone. Sometime after that, he'll host a new weekly variety show on HBO Max. When we left off, we were talking about dealing with depression. He said he'd been feeling better and wasn't brooding so much about the show when he goes home.


GROSS: Do you think some of that is just kind of getting older and just having more perspective?

O'BRIEN: Definitely. I definitely think - I think getting old has a - gets a bad rap.

GROSS: Well, you're not old. You're older...

O'BRIEN: So far...

GROSS: ...Than you were.

O'BRIEN: ...I'm - well, I'm older than I was. But it's all relative. If you asked a 19-year-old YouTuber, they would probably say, Conan O'Brien, didn't he fight in the Civil War?

GROSS: (Laughter).

O'BRIEN: (Laughter) I mean, I'm probably the oldest person they can imagine. Like - but, you know, it's all relative. But yes, I completely understand. I've been lucky. And I've been healthy. And I move around a lot. And I pretty much feel the way I did when I was in my 20s. So I'm very lucky that way. But I have found when people get rhapsodic about their childhood and say, ah, my boyhood, nothing will ever be as good as that, I don't understand what they're talking about because I found youth to be very scary and intimidating. And I put a lot of pressure on myself. And I had big expectations. And I didn't know if it was going to work out.

It wasn't bad. It wasn't traumatic. It was just - I find that as I get older, my perspective has changed. And I can sort of see the importance of the real things and the unimportance of the silly things.

GROSS: So your father is an infectious disease expert - specialist. And your mother, until she retired, was a partner in a law firm. So growing up with that, it's, in a way, all about consequences like, germs that can kill you. And...

O'BRIEN: Yeah.

GROSS: ...With your mother, like, if you do the wrong thing - I don't know what kind of law she practiced, but if you do the wrong thing, you can be sued. You can go to prison.

O'BRIEN: Yeah.

GROSS: (Laughter) You know, so...

O'BRIEN: Right.

GROSS: Did you grow up with a sense that, like, everything has, like, life-changing consequences?

O'BRIEN: Well, I think - I will simplify it for you. And that's - I - that's sort of a very interesting psychological tack you just took with, like, my dad's work and my mom's work. And that deserves further exploration. But I can simplify it for you. My parents are very Catholic. And so, yes, you grow up with a very strong sense of consequences, you know? And also, they - I grew up in - you look at my family. And there's an immigrant - an Irish immigrant - and it doesn't matter where you're from. Every generation is trying to better their circumstances from the previous generations and raising the bar for the next generation.

And then, of course, I was a workaholic as a kid and very serious. People have a hard time reconciling that. I was not some just naturally brilliant guy. I had to work. I was not good at math and science. And I made myself - like, just made myself - if I had to memorize textbooks, I would memorize them because my goal was - I don't know what I'm going to do in this world, but I need to get into a good college. And I did. What do I do once I get to Harvard? I join the comedy magazine just as a lark. And the next thing you know, that's all I care about. So I think, in my career, there's been a sense of - wait - generation after generation has been pushing the puzzle piece slowly forward. And I'm taking all of this and gambling it on being a professional goofball (laughter)...

GROSS: Right.

O'BRIEN: ...You know? And so talk about consequences. You know, to my parents' credit, they really did imbue in all of us a really powerful moral code. And so we've had that since we were kids, too. And those can feel like big consequences, you know.

GROSS: You know, with self-punishment, I sometimes think there's a sense of - like, if you punish yourself and if you're penitent in some way, that it will avoid a harsher externally given punishment. Like, I know I did wrong. I've punished myself, so you don't have to do anything. I've taken care of it. It's almost like, you know...

O'BRIEN: Right.

GROSS: ...Preemptive punishment. But it could be, like, so damaging.

O'BRIEN: Well, the other way - just as you were describing that - it's where self-deprecating humor comes from. And you know...

GROSS: Right. Right.

O'BRIEN: ...That's my milieu is self-deprecating humor. But I'll make fun of myself before Terry Gross can because you're known to rip people apart on your show.

GROSS: I know. I know.

O'BRIEN: So cruel.

GROSS: (Laughter).

O'BRIEN: You're the Rickles (laughter). You're the Rickles of the airwaves. But when I did my first late-night show ever, all the press had been about, can he replace Letterman? And how can he? And Letterman is the best ever. And Letterman was wronged. And this is the idiot that NBC came up with to cover up their mistake. And it's the worst. And that was sort of the story. I remember it at the time - some people at NBC saying, just don't mention the Letterman thing when you go on the air. And I thought, well, that's the dumbest thing I've ever heard of.

So we wrote - I had an idea. And we wrote this cold opening, which was me waking up in the morning. And I turn on the TV. And it's two people from "Entertainment Tonight" - reporters saying, can Conan be as good as Letterman? This is the big day. Can he do it? - and me smiling like an idiot - a grinning, confident idiot - and then marching down the street to Rockefeller Center. And everyone I encounter says, better be as good as Letterman.


O'BRIEN: And every single - and it gets more and more absurd until a horse goes (imitating horse neighing) better be as good as Letterman.

GROSS: (Laughter).

O'BRIEN: And I'm smiling and smiling and smiling, and then I finally get to my dressing room and I go in, and I'm whistling happily getting ready to do the show. And I make a noose.


O'BRIEN: I put my head in it. And just as I'm about to hang myself, there's a knock on the door, and they say, Conan, it's time. Now, the people at NBC were appalled. They were like, you can't do this. And I'm like, no, no, no, this is exactly what we have to do. We have to go right at it. And it turned out people, to this day, tell me they - that was the first time they ever saw me, and they really loved that.

And that is very me, which is I'm going to mock myself before you can. And it's tricky because you can overdo it, and it's all - you know, it's preemptive. And that's exactly what you're saying, which is self-flagellation and punishing yourself is a way, ultimately, of being in control. Because if I hurt myself, then I've handled the punishment and no one else has to. And it can get - as we know, it can turn into an S&M fetish.


O'BRIEN: And it can also, as we all know (laughter) - but it can - you know what I'm talking about. Anyway - but it's very much - it's all about control. And comedians are the ultimate control freaks. So we're trying to control how you feel about us at any given moment. So, it's - I will find this all ridiculous before you can find me ridiculous.

GROSS: So we were talking about self-punishment. What were you actually punished for when you were young?

O'BRIEN: The thing I remember most clearly is I think I'm the last person who's - at least of my generation, but maybe - I don't think there's anyone after me who ever had their mouth washed out with soap.

GROSS: Oh, you really did that? You really had it?

O'BRIEN: I did. I had my mouth washed out with a bar of Dial soap, and I hope this becomes a plug for Dial soap. But it was not my parents. My parents are away, and they had someone who - I remember very clearly she was from Prince Edward Island. And she was older, and I think came from this sort of different culture. And so she had, like, this 1930s mentality towards discipline. And I don't even think I said anything that bad. I don't think I said a swear word 'cause I never swore when I was a kid. I think I probably just was a little bit of a wise guy.

And I remembered she took me to the second floor of our house, and there's this old marble sink, and she took out a bar of Dial soap and made me run it back and forth in my mouth. And I remember that soap cakes on the top of your tooth. That's what I remember really clearly. And I've since told people. Yeah, I remember the time I got my mouth washed out with soap, and they say to me, did you grow up in, like, 1910?


O'BRIEN: When did that happen? And it was a total anomaly, but, no, I think we would get in trouble if we, you know, mouthed off or were disrespectful to my mom. You'd get sent to your room - nothing - you know, there were no beatings. There probably should have been. I'd be a better person today had I'd been beaten. But...

GROSS: Boy, you know that was always...

O'BRIEN: ...No, there was nothing...

GROSS: There was always an expression, like, you have a filthy mouth. I'm going to wash your mouth out with soap, and I've never knew anyone until now who actually had their mouth washed with soap. I would think it's really bad for your mouth tissues, which are sensitive, to have Dial soap all over them.

O'BRIEN: Terry, I wish you'd been there at the time.

GROSS: Yes, I would have warned her about the medical repercussions of this form of punishment.

O'BRIEN: I wish you could have materialized and told this hill folk from Prince Edward Island...

GROSS: This is not a good thing.

O'BRIEN: I wish you had said, you know, excuse me, pardon me, I worry about his mouth tissues.

GROSS: (Laughter).

O'BRIEN: I don't think this is the proper use of - maybe a liquid soap. Is there a liquid Dial soap in the house? I think that would be softer, and he could expectorate it more easily. Who are you? I'm Terry Gross. I'll become famous in about 15 years. Goodbye. And then you disappear.

GROSS: Did it prevent you from ever mouthing off again to anyone?

O'BRIEN: No, of course not.

GROSS: Obviously not.

O'BRIEN: No, it doesn't - it's complete proof that capital punishment doesn't work. No.

GROSS: There we go. We made the jump (laughter).

O'BRIEN: We made the jump. It doesn't work.

GROSS: We're listening back to the interview I recorded last year with Conan O'Brien. We'll hear more of the interview after we take a short break. This is FRESH AIR.


GROSS: This is FRESH AIR. Let's get back to the interview I recorded in October of last year with Conan O'Brien. Last week, he announced he'll end his late-night TBS show in June and then host a new weekly variety show on HBO Max.


GROSS: Your TBS show starts with this montage of you - of, like, Conan through the years, starting with you when you're a very young child and then being, like, an older...

O'BRIEN: Yeah.

GROSS: ...Child and a teenager and an adult and then having your own shows. So I wanted to spend a little more time in the young Conan years. You love music, and you play guitar. You sing. You don't try to pass yourself off as a professional musician, but you clearly love music.

O'BRIEN: Oh, God, no.

GROSS: In the studio where you are, there was a guitar sitting there. And during the soundcheck, I heard you just playing around with it. Would you be willing to just play and sing something that you were so proud you learned when you were young, when you first picked up a guitar?

O'BRIEN: When I first picked up - oh, well, OK. This is - when a comedian picks up a guitar, unless he's Steve Martin, it's time to go. It's time to get out, so you've been warned. Yeah, there's a, I think, kind of out-of-tune guitar here. And I - yeah, I was just in a room. I come into this room, and I'm messing around with the guitar when, suddenly, I realize you're here. And then you have a gotcha moment of...

GROSS: (Laughter).

O'BRIEN: We can make him do this. But hold on.

GROSS: (Laughter).

O'BRIEN: The only reason I play guitar is because when I was in college, I really got into the music of the early, early "Sun Sessions" of Elvis Presley. So, you know, I'd always known Elvis as the guy in the jumpsuit, and then I heard those early, early recordings. And so the first thing I learned was Elvis' version of "Blue Moon Of Kentucky." And I can just give you a second of it. But he played this, and it was a bit of a scandal at the time because this was not the way you were supposed to play "Blue Moon Of Kentucky." And this just makes me happy. So, again, my apologies.


O'BRIEN: (Singing) Well, I said blue moon, blue moon, blue moon keep on, keep shining bright. Well, blue moon, keep on shining bright, going to bring me back my baby tonight. Blue moon, keep shining bright. I said blue moon of Kentucky, won't you keep on shining? Shine on the one that's gone and left me blue. I said blue moon of Kentucky, won't you keep on shining? Shine on the one that's gone and left me blue. 'Cause it was on one moonlight night, baby, stars shining bright, wind blowing high. And my love's said goodbye. Said blue moon of Kentucky, won't you keep on shining? Shine on the one that's gone and left me blue.

Something like that.

GROSS: Yeah, so I loved it. That was great. You really put yourself into that.

O'BRIEN: Why are you crying?


GROSS: That was great. I'm trying to picture you as, like, a 10-year-old or 13-year-old trying to be Elvis...

O'BRIEN: I was a little older than that.

GROSS: ...In your bedroom.

O'BRIEN: I think I was about 18.


O'BRIEN: Yeah, that's where the hair came from and...

GROSS: Right, yeah.

O'BRIEN: That's why I wanted - I really wanted - I wanted black hair. And, you know, keep in mind, this is, you know - it's all the wrong time. I'm supposed to be listening to The Clash or something. I'm supposed to - I was always not in my time. You know, when I was a kid, the movies I'm supposed to be watching as I'm coming of age - "Clockwork Orange" and, you know, just the great, you know - I'm supposed to be watching "Marathon Man" and all that kind of stuff. And that's not what I'm doing. I'm watching Jimmy Cagney in "Yankee Doodle Dandy." I'm watching "Angels With Dirty Faces." I'm watching movies from the '30s, so my timing is always wrong. I'm listening to '50s Elvis, but it's at the wrong time, so I don't know. I've got a problem.

GROSS: Conan O'Brien, it's been great to have you back on the show. Thank you so much. And good luck with all the new projects you have now.

O'BRIEN: Thank you. And you are one of my all-time favorite people to talk to. And you're really brilliant at this. And it's a joy, so thank you so much for having me on. This is free therapy. I appreciate it.

GROSS: Oh, thank you so much for saying that. My interview with Conan O'Brien was recorded last year in October. Last week, he announced he'll end his TBS late-night show in June and that he'll host a new weekly variety show on HBO Max. After we take a short break, jazz critic Kevin Whitehead will review a new collection of Sonny Rollins studio and live recordings from 1967 that have never been released before. This is FRESH AIR.

(SOUNDBITE OF MUSIC) Transcript provided by NPR, Copyright NPR.

Combine an intelligent interviewer with a roster of guests that, according to the Chicago Tribune, would be prized by any talk-show host, and you're bound to get an interesting conversation. Fresh Air interviews, though, are in a category by themselves, distinguished by the unique approach of host and executive producer Terry Gross. "A remarkable blend of empathy and warmth, genuine curiosity and sharp intelligence," says the San Francisco Chronicle.
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