'Conan O'Brien Needs A Friend' Is A Joke Name For A Podcast — Sort Of

Oct 2, 2019
Originally published on October 7, 2019 11:22 am

Conan O'Brien has been hosting late-night TV shows for 26 years — longer than anyone else currently on the air. So when a colleague suggested he start a podcast, he initially balked.

"My initial reaction was, 'Why would I do a podcast? I have a television show,'" O'Brien says. "That should be enough for anybody."

But then O'Brien thought more about the prospect, and he began to reconsider. On television, conversations with guests were constrained by TV cameras and commercial breaks; a podcast would free him to proceed more slowly and dig deeper in conversations.

The podcast, Conan O'Brien Needs a Friend, featuring O'Brien's conversations with comics, actors and writers, launched November 2018. Its second season starts Oct. 7.

O'Brien says the title of the podcast is a joke — sort of. "Sometimes when you're in the public eye, it can get murky as to who's really my friend. Who's going to come visit me in the hospital? Who's going to come over to my house when my dog dies and drink cocoa with me? Who are those people?"

He appreciates how the podcast allows him to "mind meld" with his guests. "Suddenly all these people who I know in the comedy world, and some in the political world who I've known, and we've chatted, and we've had these seven, eight, nine minute chats on television — I can sit down and we can just go down a deep, deep, deep well, and it's fascinating," he says.


Interview Highlights

On how the conversations on his podcast differ from those he has with guests on late-night TV

On television ... it's a very presentational way of having a "conversation." And this sounds like I'm making a joke, but you need to get makeup. They put makeup on you — especially someone as translucent as I — so that you show up on television. So every day I'm in a chair and they're painting my skull so that I appear somewhat human. And then the people I'm talking to are painted. And then there's an audience there and cameras. And so I've grown accustomed to that and there's a lot that I love about it. ... But [on the podcast] I'm finding that ... I can sit down and have a really long conversation with Ben Stiller — someone who I've known since I met him at Saturday Night Live in, I think, 1990 or 1989 — I've never really had a long conversation with him.

On landing the job as host of Late Night in 1993

Say what you want about my career: Someone can like me; they can despise me; they can completely not care; or be completely neutral about me; but everyone would have to agree that it's a really unusual career. Just completely unprecedented. The way that I got onto the Late Night show was absurd. Basically, Lorne Michaels took a complete Hail Mary pass and said, "I know this writer and he has 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." I mean, that wouldn't happen today. Today if there was a major late-night spot open, there would be 600 candidates from 600 different cable shows with thousands of hours of content.

On being on the brink of cancellation during his early career

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 un-cancel 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 I think I just got lucky and it caught on just at the right time.

On the nationwide comedy tour he did after a period of conflict that led to him giving up the Tonight Show in 2010

It was therapeutic and satisfying. All I ever wanted to do was make people laugh. I know that sounds corny. 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. ... I think it was obviously very painful to have to give up the Tonight Show. And so 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 or on the plane. When that tour was over I was skeletal.

On getting help after the comedy tour ended

I had always done some therapy, but I got a lot of therapy, and I got some help with medication. That helped a lot. The smartest thing I ever did in my life was to marry my wife in 2002. It's been 17 years, and she's just a great partner, and very emotionally intelligent, and my best friend. So she helped me through this. And you have kids, too — I have two children, so that puts things in perspective. ... All of those things helped me enormously. I've since become a big advocate for people — if they're going through something and they're having a hard time — talking to somebody, and getting some professional help.

On how late-night TV has changed since he started

I launched my TV show shortly after Johnny Carson retired, so I'm still part of that era. That's the era I come into. There's hardly any late-night shows, and having a late-night show is this incredible rarity. There are very few of them. It's like you're a senator in Montana in 1880. You get to keep that job for 80 years and then get buried on your massive ranch. That's how it felt back then. And of course that all, it started slowly, and then it's just changed multiple times. And now, if you and I try to right now list all of the late-night shows that exist ... we'd be hard-pressed to name them all and would forget some because there are that many. So it's just different.

And I think when it first starts to happen, the natural reaction is, "How do I maintain my position? How do I keep what I have?" And I think once you realize the foolishness of that, and just what a waste of time it is, and ultimately unproductive, and just say, "You know what? I like a bunch of these other shows. These people are all very good." And late-night talk shows have become more specialized. ... The shows are completely different from each other, and everyone's working a certain niche, but a lot of them are really good.

Ann Marie Baldonado and Thea Chaloner produced and edited the audio of this interview. Bridget Bentz, Seth Kelley and Patrick Jarenwattananon adapted it for the Web.

Copyright 2019 Fresh Air. To see more, visit Fresh Air.

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. My guest is Conan O'Brien, who's been up to some new things. He changed the format of his late night TBS show and cut it back to half an hour. He now has a popular podcast called "Conan O'Brien Needs A Friend," featuring his conversations with comics, actors and writers. This weekend, his production company, Team Coco, is taking over 10 comedy clubs in 10 cities around the country presenting famous and lesser known comics. Conan O'Brien was a comedy writer having worked on "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, and a lot of people thought he wouldn't make it. But now he's been hosting late night shows longer than anyone - 26 years. His career has taken some surprising twists and turns, which we'll talk about. But he's never stopped being funny. Season 2 of his podcast, "Conan O'Brien Needs A Friend," starts next Monday, October 7.

Conan O'Brien, welcome back to FRESH AIR. It's been a long time, and it's a great pleasure to have you back. The podcast is called "Conan O'Brien Needs A Friend." My guess is that you have friends. You just don't have time to actually talk with them.

CONAN O'BRIEN: That's very good. Yes, I have friends. What's interesting is that the title of the podcast was - it's kind of a joke, but, as Freud would tell you, there are no jokes. There is a grain of truth in it, which is for years I've gotten to know a lot of people, and we're friendly, but sometimes when you're in the public eye, it can get murky as to who's really my friend. Who's going to come visit me in the hospital? Who is going to come over to my house when my dog dies and drink cocoa with me? Who is - who are those people? And it is sort of an exploration of, are we really friends or are we just people that are in the same business working at the same shoe factory known as show business? And we see each other when we check in and we see each other when we check out and we're not really particularly close. Do you know what I mean?

GROSS: Yes, I know exactly what you mean. Are there people who are close friends who you've interviewed, like, say, Lisa Kudrow who you've learned things from by actually doing something more formal like an interview rather than just having dinner together?

O'BRIEN: Yeah. I think - I mean, I've known - Lisa and I really got started in the business together as 22-year-olds just out of college coming to, you know - and we met at an improv class. So it'd be hard-pressed for me to learn anything about Lisa that I didn't already know. I mean, she - we both had odd jobs. And we used to meet at a du Parcs (ph) coffee shop. And I would talk about, well, someday I'll have a show, and you'll be famous, and you'll be on my show as a guest - I mean, the kind of crazy talk that lots of people who are deluded have when they're 22. Only, in our case, it turned out to actually happen. So it'd be hard-pressed for me to learn anything new from Lisa when I had her on the interview.

But there are plenty of people who I've known over the years and you start to talk to them - like, I had a conversation with Stephen Colbert, and I didn't intend for it to go this way, but we really did start to talk about anxiety and how we were both anxious Catholic kids and how we had sort of a punitive inner voice and this sort of emotional number we each did on ourselves. And it went into Stephen talking a lot about his pain. And we came out of there of the interview, and I didn't - I think I'd connected with him in this way that I had never thought I could.

And I have to say it's just a labor of love, the podcasts. I just thoroughly enjoy it, and it allows me at my age after having been in - you know, I started when I was 22. I'm 56 now. And I'm having more fun at this stage in my career than I've ever had before. And I don't think many people get to say that.

GROSS: 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?

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.

(LAUGHTER)

O'BRIEN: Larry King used to - 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.

(LAUGHTER)

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. And that's the stuff that, as I get older, I'm more and more interested in, which is something that's not just funny if you've read the news today. Do you know what I mean? It's going to be...

GROSS: Yeah, definitely, definitely.

O'BRIEN: ...Funny. It's funny if someone sees it online. And I think that's something that's - I'm happy about is I'm constantly having - because of YouTube - total accident - but because of YouTube, people will see something that I shot 20 years ago. But it's me, you know, going to the nurse and finding out that I have a heart murmur, and it's all happening on - in real time (laughter).

GROSS: Wait. Did you find out for real when she - this was a whole bit where you had, like, a cold, so you went to see the doctor or the nurse. And then you insisted - she kept telling you, everything's fine.

O'BRIEN: Yeah.

GROSS: And you insisted that she listen to your chest. And she said, did anyone ever tell you...

O'BRIEN: Yeah.

GROSS: ...That you have a heart murmur?

O'BRIEN: It's true, yeah.

GROSS: She used a different word for it, but - and you looked really...

O'BRIEN: Yeah.

GROSS: ...Surprised. And I wasn't sure...

O'BRIEN: Yeah, I was. I was.

GROSS: ...Whether that was shtick or real.

O'BRIEN: No, no, no. It was not shtick. It was absolutely real. And I think that's why it reads as funny. I'm fine, by the way. I've never had any issue.

GROSS: Well, that's good.

O'BRIEN: Yeah. This is Conan O'Brien's last interview, by the way.

GROSS: (Laughter).

O'BRIEN: Thankfully, I never had any issue.

GROSS: So...

O'BRIEN: Terry Gross had the last interview with Conan.

GROSS: (Laughter).

O'BRIEN: 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...

GROSS: Yes, OK.

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

GROSS: Yes.

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. Well, let's take a short break here, and then we'll talk some more. If you're just joining us, my guest is Conan O'Brien. And, of course, he has his TBS show at 11 o'clock at night. But he also now has a podcast. The second season is about to start. It's called "Conan O'Brien Needs A Friend." Season 2 starts October 7. We'll be right back. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. And if you're just joining us, my guest is Conan O'Brien. In addition to hosting his TBS 11 o'clock show "Conan," he's now deep into the podcast world. The second season of his own podcast, "Conan O'Brien Needs A Friend," starts October 7.

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.

GROSS: My guest is Conan O'Brien. His late-night show is at 11 on TBS. The second season of his podcast, "Conan O'Brien Needs A Friend," starts Monday. After a break, we'll talk about how anxiety and depression figure into his life and comedy. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with Conan O'Brien. In addition to his TBS late night show, he now has a popular podcast called "Conan O'Brien Needs A Friend," which starts its second season Monday, October 7. It features him interviewing comics, actors and writers.

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: 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. And I understand that all kinds of stuff is going to be showing up that's not going to be pleasant. 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. And I find...

GROSS: All right, let me stop you right there. What would - what did you find really scary about childhood? What scared you the most or made you most anxious?

O'BRIEN: Well, my father used to - my father would dress as a clown and hide under the bed and surprise me.

GROSS: (Laughter) And that scared you?

O'BRIEN: He's a very sick man. And he does it to this day, although he's slower getting out from under the bed (laughter). It takes him about 40 minutes (laughter). No, I would say - as I said, I was really anxious. And I didn't know how I fit into the world. And I was not a good athlete, so I would be get - I'd get picked last. I had a strange name. I think it took me a while to - for people to warm up to me. I was not someone who instantly showed up and everyone was like, hey, look at this Conan, you know, high five, you know? I was - I didn't click with people right away and know where I fit in the world.

So yeah, childhood was not - 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: Let's take a short break here, and then we'll talk some more. If you're just joining us, my guest is Conan O'Brien. And of course he has his TBS show at 11 o'clock at night, but he also now has a podcast. The second season is about to start. It's called "Conan O'Brien Needs A Friend." Season 2 starts October 7. We'll be right back. This is FRESH AIR.

(SOUNDBITE OF JAMES BROWN SONG, "LICKING STICK")

GROSS: This is FRESH AIR. My guest is Conan O'Brien. He hosts "Conan" 11 o'clock weekday nights on TBS. The second season of his podcast, "Conan O'Brien Needs A Friend," starts Monday. When we left off, we were talking about anxiety and depression.

So maybe I'm making too much of this, but your father was an infectious disease specialist at Women and Brigham's Hospital in...

O'BRIEN: Yeah - still is, actually.

GROSS: Still is.

O'BRIEN: Still is, actually.

GROSS: OK.

O'BRIEN: Still going strong.

GROSS: Does he still teach at Harvard?

O'BRIEN: Yeah.

GROSS: Does he still teach at Harvard, too?

O'BRIEN: Yeah. He does. I don't think he - he's not teaching right now. But he's working on a grant application...

GROSS: OK. So...

O'BRIEN: ...Right now as we speak because his specialty is microbiology and antibiotic resistance. And he's, every year, looking for more grant money.

GROSS: Oh, God. Good luck.

O'BRIEN: And my father did fight in the Civil War.

GROSS: Yeah.

O'BRIEN: So...

GROSS: (Laughter).

O'BRIEN: ...He's been around a while. He's doing a good job.

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 generation.

So my people come over from Ireland. They work in the mills in central, you know, Massachusetts. Then, you know, if you can get out of working in the mills, you're doing what my grandfathers did, which was you're either a traffic policeman in Worcester, Mass., or you work your way with no college education as my other grandfather did into being a teller at a bank to being the person sort of organizing the bank to being someone who's helping to run the bank. And then what are their kids do? Their kids get full scholarships and go to college and then go on to graduate school and become - you know, get a law degree and a medical degree. And so everyone's bettering the situation that they inherited 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.

(LAUGHTER)

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.

(LAUGHTER)

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.

(LAUGHTER)

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 at the end of the day, so many of the problems in our life are us trying to assert control where we don't have a lot of control. Comedians are the ultimate control freaks. So we're trying to control how you feel about us at any given moment. So, yeah, on a - on some level, a lot of, you know, humor is preemptive. 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?

(LAUGHTER)

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: All right. I'm going to take a short break here, and then we'll be right back. If you're just joining us, my guest is Conan O'Brien. And in addition to his 11 o'clock late night show on TBS, he has a podcast that's about to start its second season on October 7. And it's called "Conan O'Brien Needs A Friend." It's very funny. We're going to take a short break. Then we'll be right back. This is FRESH AIR.

(SOUNDBITE OF CLARK TERRY'S "IMPULSIVE")

GROSS: This is FRESH AIR, and if you're just joining us, my guest is Conan O'Brien and, of course, he hosts his "Conan" late-night show on TBS at 11 o'clock. He also has a podcast that's about to start its second season. It's called "Conan O'Brien Needs A Friend," and he interviews a lot of fellow comics and comedy writers and an occasional first lady. And sometimes, it's just, like, really funny. And sometimes, it just gets to, you know, pretty deep stuff. And he has, like, scripted podcasts from Team Coco and new things going on too.

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.

(SOUNDBITE OF GUITAR PLAYING)

O'BRIEN: (Singing) Well, I said blue moon, blue moon, beer 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?

(LAUGHTER)

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.

GROSS: Oh, OK.

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.

Conan O'Brien hosts "Conan" weekday nights at 11 on TBS. The second season of his podcast, "Conan O'Brien Needs A Friend," starts Monday.

Tomorrow on FRESH AIR, my guests will be New York Times journalists Julie Hirschfeld Davis and Michael Shear, authors of the new book "Border Wars: Inside Trump's Assault On Immigration." Part of the book is about some of the more extreme or absurd ideas Trump has come up with, like creating a border moat filled with alligators or snakes. I hope you'll join us.

(SOUNDBITE OF SULLIVAN FORTNER'S "PHOEBE'S SAMBA")

GROSS: FRESH AIR's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. Our associate producer for digital media is Molly Seavy-Nesper. Roberta Shorrock directs the show. I'm Terry Gross.

(SOUNDBITE OF SULLIVAN FORTNER'S "PHOEBE'S SAMBA") Transcript provided by NPR, Copyright NPR.