Conan O’Brien: Still Curious after 10,000 Interviews

Conan O’Brien
I’m Alan Alda, and this is Clear and Vivid, conversations about connecting and communicating
I am not the great Host with a capital H, who’s sitting back in my chair and the guest needs to prove themselves to me. Even if I’ve been around for 26 years, I have to roll up my sleeves and get down in the mud with them as a fellow human being. I think that’s key, this sense of parity, that we’re in this together. We’re both humans and let’s try and figure this out.
Conan O’Brien has hosted the talk show “Late Night” for 4000 hours, and by now, you’d think he’d be sick of talking. But he came to our studio in Manhattan and sat down for a conversation that was both fun and thoughtful. I’d been on his show a couple of times and ran into him on the street once, so I didn’t really know Conan. But I sensed there was a serious person behind the funny. And I saw how astute he was right at the beginning when he started by flattering me.

Alan: 00:00 Well, I’m so glad to have you here today, because I admire you very much.
Conan: 00:04 Oh, well. Thank you very much. Mutual. It’s a big deal. Our ships have crossed a few times and it’s always been a big, big deal for me. So I’m thrilled to be here.
Alan: 00:18 That’s wonderful. I really love the way you went from, the way the public heard this story was you went from writing to performing.
Conan: 00:27 Mm-hmm (affirmative).
Alan: 00:28 Zippity-do.
Conan: 00:29 Yeah.
Alan: 00:30 Was it really as quick as that? Did you just jump off the cliff and go into performing? Or did you work out a little bit in clubs or something?
Conan: 00:38 I had done improvisational work and I had gotten up onstage many times. But yes, it is a fair characterization to say for me to have gotten the job that I got based on the skill set that I had at the time was absurd. It really was absurd and Lorne Michaels said, “This kid has something and if he can get the time, I think he could really be great.” But it was a huge leap of faith on his part.
Alan: 01:15 Where you writing for Saturday Night Live then?
Conan: 01:18 No. I was writing for The Simpsons. I had written for Saturday Night Live and I was always the writer, and this is kind of a tradition, Mel Brooks had been the writer who performed in front of the other writers and acted things out and put them on and …
Alan: 01:32 Did you do that?
Conan: 01:32 I was the guy who was always up on a table and-
Alan: 01:35 A table. Tap-dancing?
Conan: 01:36 … dancing. Yes. Tap-dancing and doing things and the way that I would write his sketches, I had to kind of act it out. I would sometimes do things just to make other people laugh and they would say, “Well, that could be a sketch.” I’d say, “You know, I think you’re right.” So that was how I found a lot of things.
But to go from where I was in 1993, in April of ’93, to go from that stage and to go right on to being on television every night for an hour was insane. It was insane. To this day I don’t know how we pulled it off. I have to give a lot of credit to dumb luck. I think they wanted to cancel me. I think, in fact, there was a meeting where they did cancel me. But they didn’t-
Alan: 02:28 But they didn’t tell you.
Conan: 02:29 No, no. But they forgot to write it down. No, I think they did cancel me at one point. Then they said, “We don’t have the replacement ready yet, so let’s give him another couple of months until the replacement’s ready.” But then by then the numbers had ticked up a bit and we were … But it was just skin of our teeth.
Alan: 02:49 Was there a moment early on where you said, “Oh, oh. I get it. Here’s what I have to do”?
Conan: 02:54 There was a moment early on where I realized universally the critics said, “This guy is terrible.” Everyone said, “This is no good,” except for some reason, there was a critic for the New York Times, I think, named John O’Conner, who wrote a really lovely piece that said, “There’s a fine madness here.”
I think he acknowledged the rough edges, but said there was a fine madness and he could really see how this was very different from what had come before and what Letterman had done and this could be really special. No one agreed with him and I think maybe he probably changed his mind.
Alan: 03:35 And said, “You’re right. You couldn’t get it back from the copyboy.”
Conan: 03:37 Exactly, yeah. “Now, I didn’t mean Conan O’Brien. I meant Conan O’Ryan.” But I was filled with a lot of despair, but what I knew was I was working in front of a live audience and every night things got a little better and they would laugh more and more. I remembered thinking, “If it’s working in this little room, maybe I just need to focus on that. And the rest will seep out through the magic of television.”
Alan: 04:17 That’s interesting. It sounds like you’re saying you began to focus more on the people in front of you.
Conan: 04:24 Yes.
Alan: 04:24 Instead of thinking about, “Oh, the camera’s picking this up. I’ll play to the camera.”
Conan: 04:28 Yep. Yes. It wasn’t just the people in front of me, but I will … So much comedy, so much is just, and acting, I’m sure, I’m not an actor, but is being in the moment and being truthful to that moment.
Alan: 04:28 Yeah.
Conan: 04:46 So I felt that if I could get in there, if I could just tune out all the noise and follow my instincts, which I did have faith in, then it would work. If I got the time. The “if” is a big thing. We all know that in television, there are plenty of things that are just starting to click and starting to work and then they get canceled. So …
Alan: 05:13 Yeah. Yeah, for some reason, patience is not built into the process.
Conan: 05:19 No. And a lot of times things aren’t going to get much better. But I’m very connected to my gratitude. There’s a lot of people who have some measure of success and they really think it’s all them. I think you’re making a big mistake if you don’t … Yes, I work hard and yes, I have some ability and I’ve made the most of what I had, but I also got really lucky. I mean, sort of unprecedented luck in 1993 to get that shot. Then to survive the two years I had to survive.
Alan: 06:01 Now you’ve been on the air as a host of a late-night talk show longer than anybody doing it now, right?
Conan: 06:07 It’s ridiculous. Yeah. And what I’ve found is interesting, I’ve been on 26 years and when I started, I started just after Johnny Carson retired. You remember he did 30 years.
Alan: 06:07 Yeah.
Conan: 06:19 And everyone acted like it was the moon shot: “That will never be done again. He was on TV for 30 years.” I think Dave subsequently did, I believe, 33 years. I had to be reminded that I was at 26. It feels silly.
One of the big things that keeps occurring to me is that I went from being the young punk. I mean, for years I would walk into a restaurant and people younger than me were excited. But anybody, when I was in my thirties, if I walked into a restaurant, anybody in their fifties or sixties would look up from their food and look at me. I could see them say, “Looks like a [inaudible 00:07:08],” and then a look of disdain and back to their food.
Alan: 07:12 Because of your age? Or because you …
Conan: 07:14 I know. It was just because they just heard, “Oh, that guy. He’s supposed to be terrible.” And-
Alan: 07:18 Oh, right. What a way to, what a reputation to get.
Conan: 07:21 Yeah. I probably should’ve stopped going. It was just one restaurant and I probably should’ve stopped going there.
Alan: 07:26 Same doubt.
Conan: 07:26 Yeah, it was the Disdain Café. I remembered it flipped from being the young, I was the young punk forever. Then overnight, I want to say about five years ago, I became the grand old man. There was no in-between. Do you know what I mean?
Alan: 07:26 Yeah.
Conan: 07:51 Then all the questions are, “So you’re still doing that? Do you think you’re going to keep doing it?” They talk to you like you’re … “Would you like some help to the bathroom?”
Alan: 08:01 Yeah. You know, it didn’t occur to me to ask you either of those questions.
Conan: 08:04 Yeah. Yeah.

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Alan: 08:05 I’m interested to know, because you’ve now in these 26 years interviewed an awful lot of people.
Conan: 08:11 Yeah.
Alan: 08:13 Our show here is a lot about relating and communicating.
Conan: 08:13 Yes. Yeah.
Alan: 08:16 So how you relate to your guests, your interviewees, really interests me. You have a philosophy of interviewing? You have a theory about it?
Conan: 08:27 I do. One thing is I think is really important is it’s your job if you’re interviewing someone to find out or to come up with what is interesting to you about them. You …
Alan: 08:47 Ah, what you’re interested in.
Conan: 08:51 What I’m interested in them about them and what makes them interesting and what’s going to kindle my natural curiosity. What’s going to do that? So you need to dig for that sometimes. There are a lot of people where it’s easy. They’re just fascinating people. I would not have to if …
The times you’ve been on my show, I haven’t had to manufacture, “Gee, what is it about Alan Alda that’s interesting?” It’s all right there. It’s present. I’m really aware of your work. I’ve been watching you my whole life and I think, “Yes, there’s so much I want to talk to him about.” That’s easy.
There are other people, because it’s a volume business. I’m talking to a lot of people, and if you think about it, I’ve done over 4,000 hours of television and if there’s three people on a night, that’s a couple of hundred people, I think. I never did well in math. But-
Alan: 09:48 It’s almost a couple of hundred.
Conan: 09:49 Yeah. It’s in the high 80s. But let’s face it. You’re going to be talking to people who don’t have much to say. There’s not much. And it’s my job to prepare and find out, “Well, wait a minute. No. Where’s this kid come from?” And really try. Now sometimes you can fail to connect, but I think that’s the first job.
And the second thing it’s very important to me is … There’s some comedians who comedy’s all about status; comedians that take the stage and they take control and it’s alpha male. I’ve never been comfortable with that.
My philosophy has always been I’m not better than the person I’m talking to. There needs to be some humility involved. I need to try and relate to them and like in improvisation, make it work with them. I am not the great Host with a capital H, who’s sitting back in my chair and the guest needs to prove themselves to me.
Even if I’ve been around for 26 years, I have to roll up my sleeves and get down in the mud with them as a fellow human being. I think that’s key, this sense of parity, that we’re in this together. We’re both humans and let’s try and figure this out.
Alan: 11:22 Yeah, one of the ground rules of improvisation is that you need to make your partner look good.
Conan: 11:27 Yes.
Alan: 11:28 Not use them for your own purposes.
Conan: 11:30 Yeah.
Alan: 11:31 It’s especially difficult if somebody who’s devoted to comedy is interviewing somebody and they feel that any way they can get a laugh out of them or at their expense-
Conan: 11:44 Yeah. At their expense.
Alan: 11:45 … yeah, is not such a good approach. Because then the other person looks like a schlemiel.
Conan: 11:49 A schlemiel, which is an old Irish term.
Alan: 11:52 It’s a Gaelic term.
Conan: 11:54 I come from the Schlemiels. The Schlemiel Mountains north of Dublin.
Alan: 12:01 But you bring to mind. We’ve only met, except once in the Central Park West we met late at night on the sidewalk.
Conan: 12:09 Yes. Which is really fun.
Alan: 12:11 Yeah. Yes, I keep going back there but you’re never there.
Conan: 12:16 That was back when I was working as a male prostitute and that was my beat. And then I-
Alan: 12:22 And we don’t even get mail from here. So the thing that I’m thinking of is I’ve only been on stage with you and now we’re in another interview situation.
Conan: 12:31 Yeah.
Alan: 12:31 There are things. Let me ask you what you’re passionate about. I want to know you as a person.
Conan: 12:39 Well, I’m, always was very passionate about comedy. Just something that I took very, very seriously. And-
Alan: 12:50 So does that mean you analyzed it and studied it? You have a theory about what makes things funny? Why do people laugh?
Conan: 12:56 I used to think about it. I think to my credit I didn’t overthink it, but I sucked it up like a sponge. When I was a kid, I watched all the old stuff, all the new stuff. I watched everything and I paid attention to … My father, I remembered very early on took me to see a, I think, Modern Times, Charlie Chaplin movie.
Alan: 13:19 Mm-hmm (affirmative). Yeah, that’s a great one.
Conan: 13:21 So I paid attention. Then I saw the Marx Brothers and I really sucked that up. And WC Fields I loved. Then I learned that I liked, although I, myself, am a sentimental person, I like it when my comedy is not sentimental. So I started to prefer … I liked WC Fields. I preferred him to Chaplin and I loved Chaplin’s artistry, but I didn’t want anything too poignant in my comedy. I just-
Alan: 13:49 And Fields had a caustic side to him.
Conan: 13:51 Yeah, I mean, and he was just completely unrepentant.
Alan: 13:55 Yeah.
Conan: 13:55 And I loved that and you had to really listen for his muttering asides. Keep in mind this is the 1970s, when I’m supposed to be listening to Cheech and Chong and I’m watching these old movies. And I’m-
Alan: 14:10 Ah. So you were exploring the basic foundation of comedy in a way, it sounds like.
Conan: 14:14 And I didn’t even know that. It’s just that back then in the pre-Netflix cable era, growing up in Brookline, Massachusetts, what they would show on the UHF channels, on Channel 56 and Channel 38, for content was pretty much old stuff. That’s what they had.
Alan: 14:35 Yeah.
Conan: 14:35 That’s what they filled the time with. So on a Saturday or a Sunday, I could see Horsefeathers. I could see Night at the Opera. I could see Yankee Doodle Dandy with Jimmy Cagney. I just sucked up all these old rhythms.
Then the other thing I realized is that I was watching a lot of Warner Brother cartoons, because they would show those on Saturday mornings. So Bugs Bunny, Roadrunner and all that stuff was made by master animators and joke writers in the ’40s and ’50s. They were made for the theater, so they were made for adults.
So I wasn’t watching kids’ comedy. I mean, you’d think a Bugs Bunny cartoon is for kids. You look at them, they’re really hilarious and beautifully spaced out in time. They were shown in theaters as shorts before the main picture in the 1940s and ’50s and they were meant for adults and if kids were there too, fine.
But that’s how I learned, I learned so much about timing from that. So there was all this old stuff I was getting a sense of timing from, I think, before I found the new stuff.
Alan: 15:41 Do you think that had any help for you? Did it make it easier for you to write for The Simpsons, having written already … I mean, not having seen, so many cartoons?
Conan: 15:52 Right. Yeah. I think I just picked up … I wrote a lot of comedy in college for the college humor magazine. Then by the time I got out at 22, I think I had an advantage in that some people decide, “I might want to try getting into comedy,” when they’re 22. I realized by the time I was 22, I had been thinking and writing comedy for a lot of years.
Alan: 16:23 Mmm.
Conan: 16:24 And doing it for my friends or … So I had a head start, do you know what I mean? I was very passionate about … I’ve thought about this a lot lately, but I think in my teens and my twenties and my thirties, I just spent so much energy trying to think about trying to make people laugh. And in realizing on like a Darwinian, when something doesn’t work, you just drop it. When something does work, you own it.
Alan: 16:52 So it sounds like you’re describing an intuitive approach to it.
Conan: 16:55 Yeah, I didn’t like-
Alan: 16:56 And yet I also sense that you’ve analyzed it a little bit.
Conan: 17:00 Yeah. I do analyze it some, but then I get worried when I analyze it too much, because it’s like holding on to fog. If you squeeze it, it just goes out between your fingers and it’s gone.
Alan: 17:11 What makes us laugh? Do you have any idea?
Conan: 17:14 It’s so funny. I think for me it’s images. Some people are verbal and there’s a verbal dexterity to what they’re saying. I have some verbal dexterity, but I think the thing that I always was able to do was come up with a silly image.
Alan: 17:31 Of verbally calling up an image.
Conan: 17:32 Yes. Verbally. Verbally calling up an image that everyone can see. Because I think-
Alan: 17:38 What would be an example? Have you-
Conan: 17:38 I’m trying to think. It’s-
Alan: 17:41 … You’re not under pressure to make me laugh.
Conan: 17:41 No.
Alan: 17:42 I’m just trying to get the idea.
Conan: 17:45 Man, I’m trying to think of what’s a good example of … It’ll come to me at some point, then we can go back.
Alan: 17:54 Yes, we can go back and stick it in there.
Conan: 17:55 Yeah, exactly. I think it’s why I excelled at The Simpsons and when I wrote sketches … Well, here’s an example. I wrote a sketch. This is when Oprah first, she went on an extreme diet and this is back in the late ’80s.
She lost some incredible amount of weight and it was big news everywhere. She debuted. She walked out and she was wearing skinny jeans and she had just completely transformed herself. And everyone went crazy about Oprah’s massive weight loss.
This is very cartoonish; this is how my brain works. I thought, wouldn’t it be funny if we did a sketch where someone plays Oprah and she comes out. She’s really skinny and she’s talked about how she’s lost all the weight. Then you see her point of view of people are asking questions in the audience and she’s answering them.
But then you see from her point of view. And getting special styrofoam heads made, we’d turn their heads into hamburgers and french fries and milkshakes. It was this very silly, cartoonish idea and I’m writing, so I pitched that.
They said yes. We went ahead and made the costumes. It’s very hard to do live. You’d have to cut to someone that asks a question. You’d cut to the person playing Oprah.
Alan: 19:23 You may have to quick put over hamburger heads.
Conan: 19:23 They would start to answer. But then you’d see the Oprah starting to get distracted and you’d cut back to the person with the hamburger on their head. It’s that she is starving herself and she can’t concentrate.
Alan: 19:34 She is.
Conan: 19:34 Then you see the whole show break down because she’s saying-
Alan: 19:34 Can’t do it.
Conan: 19:37 … “I want to bite.”
Alan: 19:37 That person in the third row.
Conan: 19:37 “I want to bite your head.” And then you cut back to them without and they’re saying, “Pardon me? What are you saying?” So I would say that’s very me, is I like to come up with the image.
If you and I were having a conversation and you mentioned that you hadn’t eaten lunch, I might verbally say, “Is my head turning into a roast beef sandwich right now?” It’s just a quick verbal thing, but it’s the same idea of it’s not that I said anything verbally dextrous. It’s that I put an image out there.
Alan: 19:37 Yeah.
Conan: 20:20 It cuts right to the chase and people love an image. They love an image in their head. If you can get it there quickly and you can say it just right so that they have that image in their head, and if you’ve downloaded it right into their cortex at the right moment, you can get them in a way that a sly pun won’t. Do you know what I mean?
Alan: 20:42 Yeah. Yeah. Puns are peculiar because some of them are really laborious and unpleasant to hear. Then some of them are classic and have meaning.
Conan: 20:52 Yes.
Alan: 20:53 I like it when they have meaning.
Conan: 20:54 Yes. I like it when they mean something and when they line up perfectly, you appreciate the workmanship and the craftsmanship. You go, “Oh, wow.” But I don’t know that you get a belly laugh from them. What’s the great one? Is it some of the Algonquin Roundtable? There’s that old saying, “You can lead a horse to water, but you can’t make it drink.”
Alan: 21:17 Yeah. “You can lead a whore to … ”
Conan: 21:19 “A horde to culture, but you can’t make them think.”
Alan: 21:20 “You can’t make them think.”
Conan: 21:22 And you’re just like, “Okay, that’s a 10 out of 10.”
Alan: 21:25 Yeah.
Conan: 21:26 It’s beautiful. I’m not sure I’m on the floor laughing, but I’m appreciating the beauty of it.
Alan: 21:32 Right. Right. Did you find it easier, more fun to write for Simpson cartoon characters than for real people? Because I say that because I don’t picture a cartoon character saying to you, “My character would never say this.”
Conan: 21:48 Yes. Exactly. The thing about The Simpsons that was so fun is that, if you think about it, there’s nothing that can’t happen. When you’re writing a cartoon, there’s nothing that can’t occur.
Alan: 22:00 And it’s all visual too.
Conan: 22:01 It’s all visual so that was a lot of fun. I loved writing for Saturday Night Live, but there are also limitations, which is you always needed to figure out … If I wrote a sketch and it takes place in a class at a university, but then the professor’s having a problem, has to go see the dean.
You’ve got to figure out the transition to him, Phil Hartmann, running over to another set and being with the dean. But then you have to figure out how to get him back. You’ve got to figure out where the pre-tape is. It’s all happening live, so there’s a lot of problem solving to how to do something and …
Alan: 22:42 And it gets in the way of funny, I would think.
Conan: 22:44 Sometimes. I mean, sometimes limits are great. Sometimes limits doesn’t inform the-
Alan: 22:49 Yeah. Isn’t that interesting, that limits sometimes give you more freedom?
Conan: 22:52 Yeah. I mean, sometimes they … You need some limits. It reminds me of, I mean, the best example is the Beatles, when they started out pretty much had to record almost live or to four-track. By the time they’re doing Sergeant Pepper, they have eight-track and they knock these things out. I mean, they’re so prolific.
There’s only, I think it’s a six and a half year recording career and all that work happens in a very short period of time because they just had to get on with it. They only have four tracks, so they only have eight tracks and they only have two weeks and they’ve got to get it done.
Now what happens is a group has a huge amount of success and then they’re told, “You’ve got all the time you need for your second album.” Plus the technology is, instead of eight tracks, you now have an almost infinite number of tracks. So you have an infinite amount of possibilities and almost an infinite amount of time. And no …
Alan: 24:00 You could take a nap.
Conan: 24:00 Yeah. No, you take a nap. You investigate alcoholism as a profession. Or worse. So I don’t know. Having few options can be refreshing.
When we come back, I’m curious about Conan’s interview style, and he has a good analogy to describe what he does. But first, you have to listen to this short break. Be back in a minute with Conan.
MIDROLL
This is Clear and Vivid—and now, back to my conversation with Conan O’Brien.
Alan: 24:22 When you were talking about interviewing, it occurred to me to ask you how much you were prepared for each one. I can’t remember. Did you do a pre-interview? Somebody would pre-interview the guest?
Conan: 24:33 Yes. They’d do a pre-interview.
Alan: 24:34 And would you stick to that? Would you have a list of questions? Or how much did you improvise?
Conan: 24:40 Yeah, my motto or what I learned was, I think my analogy that works is a quarterback has a plan, calls a play. But two-thirds of the time, in the play as it unfolds, the hole, the opening is supposed to be over to the right. That’s where the opening’s supposed to be.
But so often in football, the opening isn’t … They always say, “The hole isn’t where it’s supposed to be.” So a good quarterback says, “Okay, that tackle didn’t work. There’s no opening over there. I’m going to dodge off to the left. Wait. No, I’m not. I’m running off to the right. I’m going to throw it. Or I’m going to run. Or I’m going to … ”
Alan: 25:25 So “I’m going to go back to the showers where … ”
Conan: 25:26 “I’m going to go shave.” Yeah, “I’m going to go hide under the bench.” So, I mean, to me, what I like, what I believe in at the end of the day, is have a plan and then be more than willing to throw it out the window.
Alan: 25:44 When I did the Johnny Carson show once or twice, it really surprised me that it was so regimented. It seemed to me that the more money that went into a talk show, the more regimented it was.
Conan: 25:57 Right.
Alan: 25:58 And they would pre-interview me. Then right before I went on, somebody would come up to me and say, “Now, Johnny’s going to ask you this and you answer this.”
Conan: 26:09 Really?
Alan: 26:09 Yeah.
Conan: 26:10 No, we never did that.
Alan: 26:11 “This is what you told us in the pre-interview and this’ll be good for your answer.”
Conan: 26:15 Yeah.
Alan: 26:16 I was astonished.
Conan: 26:17 Yeah. I mean, we never did that and I do find that most … Sometimes the prepared stuff is really the best. And then so often going off book, if you see an opportunity, if someone slightly misspeaks and you say, “Pardon me? Wait. What was that?”
“No, I just said I probably shouldn’t mention this, but my wife … ” And like, “What is it about your wife?” Then the next thing you know, and it’s not that it’s salacious, but then you’re getting something. You can feel the energy in the room.
Alan: 26:50 Yeah, yeah. It’s alive.
Conan: 26:51 And humans, I talk about humans as if I’m not one of them, these humans everywhere …
Alan: 26:58 I was wondering that since you came in.
Conan: 27:00 Yeah, I know. I’m a ethereal figure. But when you look at … There’s something about people that I find miraculous. And this relates to what really I think an important theme of your podcast, is how do we interact? How do we communicate? How do we connect?
One of the things that has most impressed me in 26 years and 4,000-plus hours of doing these shows, I’m always amazed that audiences know when something is organic. They just do. So I’ve heard plenty of prepared stories that do fine. They do great.
But when somebody comes on the show and something starts to unfold and it starts to come off the rails and get purely improvisational, audiences smell it the way a wolf can smell blood. They just do. That’s something that’s never been explained to me. But they know it. They just know it and it’s electric.
My favorite moments, and I realized this once, is that I was looking at The Best of Johnny Carson. They were for years, I think, selling them. You can get The Best of Johnny Carson. It would be a late-night infomercial and they would show all these clips. Almost every clip was something going wrong.
Alan: 28:25 Hmm.
Conan: 28:26 A mistake. It was Johnny messing up the monologue. The boom came down too far and he grabbed it and said, “We need a cleanup in Aisle 4.” And Don Rickles breaking something accidentally. Something smashing. A dog failing to do what it was supposed to do in the Ed McMahon Alpo commercials, so Johnny comes in on his knees and pretends to be a dog on the spur of the moment.
Covering mistakes. That’s when people erupt and those become the classic moments. The famous one is the Ed Ames tomahawk throw.
Alan: 28:26 Yeah.
Conan: 29:06 On the Tonight Show, when someone was doing an ax demonstration and threw it at a silhouette. It actually hit right where the crotch is and at an angle that created suddenly an obscene and pretty much anatomically accurate three-dimensional sculpture, a phallic sculpture. This is 1962 and the audience is going and howling because it’s a mistake.
Alan: 29:30 Yeah.
Conan: 29:31 And Ed Ames, the tomahawk thrower, goes to try and remove it and you see Johnny stop him.
Alan: 29:36 He grabbed him by the arm.
Conan: 29:38 He grabbed him and pulled him back.
Alan: 29:40 He’s also timing the laugh.
Conan: 29:42 Yes.
Alan: 29:42 Because he knew that if he continued to just stand there and react to what had just happened, the laugh would build, which it did.
Conan: 29:51 Yes. Which it did and it’s something he knew intuitively. And he also learned from his idol, Jack Benny, which is …
Alan: 29:58 Wait.
Conan: 29:58 Wait. And I’ve seen in my career, God bless whatever, I was watching all this stuff as a kid and noticing that waiting and letting them laugh and letting them read your deadpan reaction is so much better than talking.
Alan: 30:22 Hmm.
Conan: 30:23 You still want the good line at the end and Johnny had it then. He said, “Welcome to Frontier Bris.” And that got a huge laugh.
Alan: 30:32 Huge laugh at.
Conan: 30:33 Yeah. But he knew and Jack Benny knew you just wait.

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Alan: 30:42 The other thing you’ve said about the spontaneous moments were the ones that became classic, where it was totally unplanned. You’ve just, when you were talking about that, you really summarized what we’ve been doing for 10 years in helping scientists be more understandable to the public.
Conan: 31:04 Mm-hmm (affirmative).
Alan: 31:05 Which is not that they make mistakes in front of the public, but that they are in a spontaneous connection with them.
Conan: 31:13 Yeah.
Alan: 31:13 Where by virtue of paying attention to the people that are trying to communicate with, they have a more spontaneous tone and you listen more. You listen more closely to that. If you’re getting what sounds like a canned commercial, you’ve learned to turn it off from years of listening to canned things.
Conan: 31:33 I think now more than ever, we have all these serious issues and we have this culture that can politicize it. And can say, “Well, that’s just a lot of mumbo-jumbo from some nerds,” and dismiss it because what do they know? Now more than ever, you need scientists.
I ran into Bill Nye the Science Guy the other day and we started talking about global warming. He was explaining to me as a human being what he thought we could do. I thought, “This is so uplifting. This is so great. And this is so … ”
He wasn’t talking down to me. He was talking to me in a very human way about what he thought the problems were and how he thinks they could be addressed and how much money it might take. I felt hope, you know? Just because I was part of it.
Alan: 32:34 And he was telling you in a way that was a fellow person and not talking down to you from above.
Conan: 32:40 Yeah, yeah.
Alan: 32:42 You know what I’m noticing as we talk, because I noticed it that night we met by accident on Central Park West.
Conan: 32:50 Mm-hmm (affirmative).
Alan: 32:52 A phrase comes back to me from my childhood where my father was in burlesque. They used to talk about comics who were always on. Never could talk straight from the heart about anything.
Conan: 33:07 Yeah.
Alan: 33:09 I saw that night that you weren’t always on. I see it now today. It’s like that’s your business.
Conan: 33:15 I’m heavily medicated.
Alan: 33:16 Oh, I didn’t notice that. But I do want to ask you one question about communication.
Conan: 33:22 Sure.
Alan: 33:24 It’s your hair.
Conan: 33:25 Yes.
Alan: 33:27 I get the impression that when you’re on the show, you comb your hair in a deliberately peculiar way. In real life, it doesn’t look anything like that. In real life it looks like a regular person’s head. Now, and when I watch it on television, you seem to have this very high pompadour as if you’re playing a character.
Conan: 33:46 Yeah. I-
Alan: 33:47 What is that? Is it just me?
Conan: 33:48 …. Well, first of all. No. You used the word “peculiar” and I take offense. I didn’t come all the way down here to be told that my hair is peculiar.
Alan: 33:56 No, not at the moment. At the moment, it’s just odd.
Conan: 33:58 No, no. But on television, it is a … My goal was for it to look like a Belgian pastry that’s in a shop window that you want to take a bite out of. It’s funny. Why do these things happen? Something along with my interest in comedy that started to grow is my interest in music from the 1950s. Early Elvis, not Elvis once he went to the big time, but when he’s first made his recordings in Memphis.
I got really interested in that kind of music and playing that kind of music and seeing if I could sing that rockabilly kind of music. Gene Vincent. I don’t know why. Again, I was out of time, because now it’s the 1980s. I’m not supposed to be listening to that. But that’s what I’m listening to and I became a little obsessive about it.
So I grew my sideburns long and I realized that my hair had the ability to, it has a wave in it and I could pile it up. I don’t know why. It’s compulsion. It’s a compulsion and I did it and I think I turned myself into a little bit of a character.
Alan: 35:13 So you continued to do it, deliberately as a kind of character.
Conan: 35:17 And it’s not even really a choice. It was like a compulsion. I just don’t know why, but maybe it’s an obsessive-compulsive. But I would pile my hair up and go out. I mean, it used to be far crazier, but if you look at some of the early shows from the ’90s, it is a 3-D structural marvel. It is …
Alan: 35:39 It’s one of the wonders of the world.
Conan: 35:42 It’s a cantilevered … It’s something that you’d have to have architects come in and say, “When it’s load-bearing, it’s coming out at an 80 degree angle.” You could hang Christmas ornaments off of it. It was an absurdity and I don’t know what I was doing. It has calmed down a lot since then.
Alan: 35:57 Well, you know, it reminds me of WC Fields. One of the things about him and only a few other comic figures in our lives, the interesting thing about WC Fields is that he created a character that was impossible to imitate without stealing from him.
Conan: 36:22 Yes.
Alan: 36:23 And nobody combs their hair that way.
Conan: 36:25 Well, for good reason. Everybody wanted to dress like Johnny Carson.
Alan: 36:32 Yeah.
Conan: 36:32 He had a line of suits and everyone wanted to be like Johnny Carson. I decided to stake out territory that nobody would want. And the hair. You know what I found helpful over the years is that it was sometimes a conversation starter. People would come out-
Alan: 36:49 And they would ask you about your hair?
Conan: 36:51 … who were famously shy or weren’t good at talk shows and they would come out and they would look at it in person. They would say, “Can I put my hand in there?” I’d say, “Go ahead.”
Alan: 37:01 “Can I get it out again?”
Conan: 37:02 Yeah. Exactly. And “What’s in there?” And the next thing you know we’re talking.
Alan: 37:09 Yeah.
Conan: 37:09 So it was a conversation starter. Sometimes a conversation stopper. But …
Alan: 37:14 Did it have something to do with the character you were playing? Did you think of playing a character as the talk show host?
Conan: 37:22 I think I had an idea that I wanted not so much to be … It’s not so much that I would be a character, but I think on some level there was part of me that thought it’s important to be easily caricatured if you’re in this business. Because there’s lots of people in comedy and so I had … There’s no mistaking me.
I’m easily drawn. A child could draw a Conan O’Brien caricature very easily, because it’s a couple of freckles, beady little eyes and then this massive dessert on my head. It was like that famous Jerry Lewis caricature, that there was that caricature of Jerry Lewis.
Alan: 38:09 Yes, yes.
Conan: 38:09 And the thing is, Jerry would still use that caricature. He used it 50 years after he no longer looked anything like that.
Alan: 38:16 Right. Right.
Conan: 38:18 He bore no resemblance to that skinny kid in 1948. But yeah, I just thought, yeah. There are Conan t-shirts that are just the silhouette of the hair. I thought, “Yeah, okay.” I see on some level why I did that. Let’s just make it something that can be reduced to about four lines.

MUSIC BRIDGE

Alan: 38:46 On your podcast, do you have a theme on your podcast?
Conan: 38:53 It’s called Conan O’Brien Needs a Friend, but again, that’s just a way in. Really, it quickly gets away from that. Mostly, I would say the theme is I talk to a lot of people in comedy. I talk to people that I intuitively want to speak with.
I would say the theme that’s emerging more than anything else is trying to dispel the notion that people who’ve had success have arrived at something that’s going to bring them everlasting joy.
Alan: 39:32 Oh, boy. What a good theme that is. I know so many people who thought, “If only I’d get rich and famous, all my problems will be solved.”
Conan: 39:40 Yeah.
Alan: 39:41 Then they got rich and famous and they realized they had more problems than they had before.
Conan: 39:44 Yeah. One of the things that I’ve seen, again, I can mostly speak to comedy, but a lot of comedians, you see it. They weren’t good athletes. They didn’t get the girl or didn’t get the guy.
They have honed this compensatory, these mechanisms. They felt vulnerable and so they developed all of this stuff. Quick reactions, jokes, masking techniques and that’s comedy. And they developed it all over years and years and years to help protect themselves.
Then what happens is they think, “When I become a famous comedian, I’m never going to feel rejection again. I’m never going to worry about money. I’m going to fix all the problems in my childhood, because I’m going to have arrived.” I think I did some of that.
I used to look at people like a Johnny Carson or a David Letterman and think, “Well, if you were that person, you wouldn’t have any problems. All your problems would be gone.” And denigrating whatever you’ve achieved, like, “Yeah, I’m not there. But if I was there, then I’d really know. If I could get to the mountain … ”
And it’s the myth of the mountaintop. “If I could get to the mountaintop like those people did. Cary Grant could never have had any problems. He was Cary Grant.”
Alan: 41:31 Mm-hmm (affirmative).
Conan: 41:33 What a stupid thing to say. It’s just not true. I like people to talk about … Obviously, I love it when they’re funny and there’s a lot of humor and laughing. But then getting them to talk about what they’re struggling with now. And I like it when people are …
I think, one of the things that’s endlessly fascinating is we have an envy culture, especially with celebrity. So with your career, people would say, “Well, Alan Alda, he’s in the 1% of the 1% of the 1% of the 1%. Like biggest TV show of all time and this amazing movie career and just revered. You have no problems.” They don’t understand that today you got up and you’re worried about things and you’re wondering, “How am I going to do today?”
Alan: 41:33 Mm-hmm (affirmative).
Conan: 42:29 “The great Conan O’Brien’s coming in.”
Alan: 42:34 I actually-
Conan: 42:35 I love that that’s a big laugh.
Alan: 42:38 I actually wondered how your hair was going to be combed.
Conan: 42:40 Yeah, yeah. I tried to behave today. But no. Just that we’re all … You’d have been one of the people when I was 20 who I would just think, “Well, he’s got no problems.” I would just think that. I wouldn’t understand. And now I understand.
Alan: 43:02 Yeah, that’s so good. And it’s good you’re bringing it out and your guests on the podcast, because it’s really much better to know that we’re all fellow humans in this. I know so many people who have really hit it in business as well as show business.
Conan: 43:20 Right.
Alan: 43:21 They have the same kind of problems. They have to grow old with grace. They have to fight disease. They have to find a way to relate to their spouses that’s better than what they’ve got now.
Conan: 43:32 Mm-hmm (affirmative).
Alan: 43:33 And everybody has human problems.
Conan: 43:36 Yeah, and I think that we as a culture, we … I see this all the time on these shows like Forensic Files that runs around the clock. It’s constantly on the show. It’s a show that’s about these terrible crimes and murders and they’re all real. They’re narrated and they all start the same way. They all say, “Joe Brewer had it all.” You know?
Alan: 44:11 Yeah.
Conan: 44:12 And they always say, “He was living the American dream.” Then they tell you, you think, “Oh, let’s hear about Joe Brewer.” Then they said, “He had a really nice … ” and then they show you-
Alan: 44:21 His car.
Conan: 44:21 … his car. It was like, “Oh, yeah. He had a Dodge Dart. He had a Dodge Dart. He was on his second marriage and he was living in this nice trailer park.” They say, “He had the American dream until it all went south.” Then he commits a murder.
The reason why they tell this story the same way every time is that we’re all children and we all like a fairy tale or morality tale. We all like, “He had it all, but then he slipped up and he fell and plummeted to the depths.” I think, I don’t know if it’s just peculiar to America, but we love the rise and the fall.
Alan: 45:04 Yeah.
Conan: 45:04 And we like it to be simple and childishly simple. So when you try and tell people nuance of, “Okay, how’s it going, Conan?” “Well, this was good, but then this was rough and then this was hard. But then I enjoyed this, but then this is a little difficult. And just worried about my, I hope my son’s good with this, but I hope my daughter … And it’s very complicated, but overall I’m quite happy. But some concern about this and some concern about that.” No.
If, God forbid, anything ever happened to me, they would say, “He had it all. And then his fatal mistake: He went on Alan Alda’s podcast.”
Alan: 45:42 It destroyed his whole career.
Conan: 45:43 Yeah, “And it destroyed him.”
Alan: 45:44 They’re yelling at me from the control room.
Conan: 45:46 Why?
Alan: 45:46 Before I let you destroy yourself further, I have to come to the end of our conversation.
Conan: 45:51 No, this has been … I’ll come back. I really love this.
Alan: 45:56 I love this too.
Conan: 45:56 It’s just fantastic.
Alan: 45:57 Maybe I’ll come on your show if you ever want me.
Conan: 46:00 That’s never happening.
Alan: 46:00 Oh, okay. Well …
Conan: 46:01 Look. I can’t afford you.
Alan: 46:04 You know, I’m just a normal person.
Conan: 46:04 I can’t afford you.
Alan: 46:06 I could come on and cry.
Conan: 46:07 Yeah, I would love, if you would be on my show, that would be fantastic.
Alan: 46:11 Well, before you go from this show, I have seven quick questions. You mind taking a chance with these questions? They’re not embarrassing or anything.
Conan: 46:18 No, I’m straight.
Alan: 46:20 They’re-
Conan: 46:20 Oh, I just assumed that was on the first-
Alan: 46:21 … That wasn’t the number one question.
Conan: 46:22 Okay.
Alan: 46:24 But here’s the first one.
Conan: 46:26 Okay. Do you want quick answers? Like pretty monosyllabic? Or …
Alan: 46:30 No. A short sentence. You’ll see. Whatever comes up.
Conan: 46:30 Okay.
Alan: 46:34 Number one. What’s the hardest thing you’ve ever tried to explain to someone?
Conan: 46:40 I would say death. Death is a hard one to explain. Explaining death to …
Alan: 46:46 Someone dying.
Conan: 46:47 Someone dying to a child. When someone’s dying, I don’t need to explain to them that they’re dying.
Alan: 46:53 You kind of want to find out what it’s like.
Conan: 46:54 Yeah, but I think when your children at a young age ask you what that’s all about …
Alan: 46:59 Yeah, that’s very tough.
Conan: 47:00 I think, I would like before I explain it to you, I need someone to explain it to me. Because I still don’t understand it.
Alan: 47:06 Yeah. Well, we’ll get into that more on your show. Your really put a real low point on this whole series.
Conan: 47:13 On all of this here and the topic is death.
Alan: 47:15 Yeah. Number two. How do you tell someone they have their facts wrong?
Conan: 47:21 I make a quizzical face. I don’t say, “You’re wrong.” I try not to say, “You’re wrong,” because that puts them on the defensive. I make kind of a quizzical face and try to say, “Really? Because I think I heard it the other way.” And I try to give them an out.
Alan: 47:21 Yeah.
Conan: 47:41 I try to give them room to maneuver to the side or to keep their dignity and maybe reconsider that the earth might be round.
Alan: 47:53 Yeah. What’s the strangest question anyone has ever asked you?
Conan: 47:58 I think when you asked me about my hair. [crosstalk 00:48:00].
Alan: 48:00 Oh. I thought that everybody’d be asking you about that.
Conan: 48:03 No, no, no. Everyone else has thought it’s beautiful and perfectly natural. And for you to call it peculiar and make it a centerpiece of this show, is the most shocking thing that anyone’s ever said to me.
Alan: 48:15 I’m trying to fix that nice guy thing.
Conan: 48:16 Yeah, yeah, yeah. Trust me. You’ve done that in many movies.
Alan: 48:20 How do you stop a compulsive talker?
Conan: 48:26 I don’t know if there’s any better way invented yet. And I think it’s one of the great advances, is the cell phone.
Alan: 48:40 You take it out and pretend somebody’s calling you?
Conan: 48:43 Yeah, because they don’t have to ring. They can buzz.
Alan: 48:45 Ah.
Conan: 48:45 And it’s a buzz that no one has to hear.
Alan: 48:47 Oh, this is great. Nobody ever said this.
Conan: 48:50 Think about it. This didn’t happen in the ’50s, ’60s. I mean, for most of humanity, this was not a possible way to end it. But now, someone can keep going on and on and on.
Alan: 49:01 So you can talk into the phone, you can say something like, “What? Is she still breathing? Oh, I’ll be right there.”
Conan: 49:06 Yes. Yes. Yeah, what you do is you keep your phone in your back pocket or in your side pocket. Put your finger up when someone’s going on for the 9th minute about the kind of drywall they’re using in a new apartment.
Then you take it out and you put it up to your ear and you just put your finger up. And you go, “Yes, yes. Hold on a second. What’s that? What’s that? Really? And fired the gun five times? I’m on my way.” And then you say, “I’m sorry. There’s a problem at home.” And you rush out.
I mean, that’s something that … People complain about this new era of technology.
Alan: 49:37 This is a great [crosstalk 00:49:38] your phone.
Conan: 49:39 Use your phone. You should do this because I know you get bothered a lot. Use it at an airport. If I’m left alone and I see people headed my way and they want to take selfies and all that, and maybe I’m not quite in that mood.
I pick up the phone and I just start talking. I wish I had a recording of the stuff I said, because it’s pure babble. I’ll pick up the phone and my assistant has seen me do it.
I’ll say things like, “No, no, no. We’ll get more corn. Let’s get six bushels of corn. Yes. Get it over to Hannity’s. Don’t know what to do. Yeah, Moroney has the idea. But make sure that we trade it for the rice, see?” And people back away.
Alan: 50:12 I can imagine them backing away.
Conan: 50:14 They do back away.
Alan: 50:15 Next question. How do you like to start up a true conversation with someone who you don’t know at a dinner party?
Conan: 50:26 I don’t like to ask them what they do.
Alan: 50:29 Right. I don’t either.
Conan: 50:37 The best way is to go off of something that they’ve said that intrigued me a little bit. Obviously, that’s the best way. But I always think a really kind of nice, simple question that starts things off if you’re at a real cold start is, “Where are you from?”
Alan: 50:53 Hmm.
Conan: 50:54 Because that’s not a status question. That’s not a … You know?
Alan: 51:00 Yeah.
Conan: 51:00 You can very easily say to people, “Hi. Where are you from?” And that’s not asking them what do you do, how much do you make. There’s nothing implied. I’ve actually have gotten into really good conversations. I do that a lot with Uber drivers or Lyft drivers is …
Alan: 51:00 Uh-huh (affirmative).
Conan: 51:19 Now, sometimes because of this immigration thing, they think that I’m …
Alan: 51:22 Yes, you’re [inaudible 00:51:25] them.
Conan: 51:25 But I do. I do speak some Spanish and I do like to know where.
Alan: 51:29 That’s nice.
Conan: 51:29 I like to talk to them about where they’re from, do they have family there. Of if they’re from eastern Russia and I just … I’m curious about, well, what was that like, and how long have you been here and do you have family back there, are you bringing them over here? So that’s a nice way to do it, I think.
Alan: 51:50 What gives you confidence? Assuming you have some.
Conan: 51:56 Yeah. I did before I came in here and you shredded me to pieces. I think age. I think getting older.
Alan: 52:05 Oh, okay. Age. Oh.
Conan: 52:05 I think I was lacking in confidence when I was younger and every year I get a little more confident, I don’t think in a arrogant way. But I get more confident about … Sounds strange, counterintuitive. I know how much I don’t know. When you’re young, you think you know a lot more than you do know and as you get older, you’re aware of how much I don’t know. And you relax into it a little bit.
Alan: 52:34 Oh, that’s well said. That’s really nice. Very nice. Last question. What book changed your life?
Conan: 52:43 Wow. Man. I’m going to go with Dianetics, L Ron Hubbard. Sorry. Suddenly, it got really quiet. And Alan, I’d like you to come with me. There’s a meeting we’re having.
Alan: 53:02 Thank you, yes. I’d like to be hooked up to the machine if you can [crosstalk 00:53:06].
Conan: 53:06 Yeah, yeah. I’d like to hook you up to a machine. Man, I am hard-pressed to think … You know, I don’t know. That is unfair. I don’t know that I can say. I love books. I don’t know that I can say one book that changed my life.
I will say a book that was very important to me is the most of SJ Perelman, which is a collection of essays. My dad loved SJ Perelman and so I read it and realized, “This is really funny. Really funny.”
This guy is very smart and these were written in the ’30s and ’40s. It had some great images in it, just terrific images and very funny. I remembered reading that and thinking, “Comedy is something smart people can do.”
Alan: 54:04 Ah. Boy, I’ve noticed that.
Conan: 54:08 Yeah.
Alan: 54:09 I’m so glad you came in for this little chat.
Conan: 54:13 Are you kidding? This is a real pleasure for me and I’d love to come back again or maybe we continue this on my show.
Alan: 54:21 Yeah.
Conan: 54:22 I’ll get back out here to New York and we’ll hook you up to the machine. I’ll start insulting your hair and we’ll see how you like it.
Alan: 54:30 There isn’t enough to insult.
Conan: 54:31 Oh, there’s enough for me to work with there.
Alan: 54:34 Thanks so much, Conan.
Conan: 54:35 Thanks so much. This is great.
Alan: 54:36 That was really great. Thank you.
END CREDITS:
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