Photo: Bobby Doherty/New York Magazine

Within the relatively unchanging landscape of late-night TV, Conan O’Brien has had an unusually eventful career. There were his rocky early days on Late Night, the ill-fated eight-month stint as host of The Tonight Show, and now the news that his TBS show, Conan, will move from an hour to half-hour episodes beginning in 2019. (Yes, the aforementioned events account for a small slice of an otherwise consistent — and consistently hilarious — 25 years as a late-night host, but still!) “There was a long time when I thought that if you just worked hard, things took care of themselves,” says O’Brien, 55, having switched from Diet Coke to red wine at the bar of the ritzy Manhattan hotel where he’s staying during upfronts week. “I’ve learned that isn’t always the case. But at no moment have I ever felt anything less than incredibly lucky that my job is to make people laugh.” Which, he notes wryly, “does still happen sometimes.”

What’s the thinking behind going down to 30 minutes?

One way I can answer this is to take you through the history of late night.

Oh, good.

[Laughs.] But quickly! Sometime around 1948 someone said about the late-night time slot, “There’s this space up in the attic that no one’s using. Let’s go in there and screw around.” And that’s what the early people in late night did. Then you got Steve Allen and Jack Paar and Johnny Carson and they turned late night into this massive part of the American experience. But there were elements of what hosts did that were about killing time. A couple of years ago, someone sent me a clip of The Joey Bishop Show. It was Joey and his sidekick, Regis Philbin, and they were vamping: “Hey everybody, it’s the show! What do you think of the show? Because this is the show!” And they were doing that for a whole hour.

And you feel like you’ve been doing your version of vamping?

That idea got under my skin. I used to love doing a whole hour; that was my assignment. I have letters that Jack Paar and Steve Allen sent me in 1993 that were like, “We’ve heard about your new posting. Good luck to you, sir!” And getting that assignment was cool, but at a certain point you start thinking, Wait a minute. Why am I still doing it the way I’ve been doing it?

Meaning you no longer saw a compelling reason to be doing an hour?

Yeah, and it was the travel shows we did that changed my thinking. There was no one standing over me saying, “This is what those shows have to be.” It was just, “Let’s go do them.” I didn’t even know what they were — I guess like Anthony Bourdain without any learning — but the more I did those shows, the more I felt, I’m passionate about these and the comedy and I like interviews but does it have to be three guests a night? There are parts of late night that feel very pro forma. At this stage in my career doing half an hour could shock me into coming up with new stuff.

But how much of moving to half an hour is a business decision rather than a creative one? The cynical way of looking at the situation is that you wouldn’t be going down in length if 10 million people were watching the hour-long show every night.

I understand that perspective, but the truth is that the initial resistance to half an hour came from the business side. They didn’t want to stop selling an hour’s worth of ads. But we’re not going to be giving them less content. We might even be making more content and just putting more of it directly online. We’re hoping to expand out into possible comedy tours and other ventures. I don’t know — I think we fit better in the current environment at half an hour. It’s possible this change ends up being a bad business decision. But I don’t think it will be.

It’s strange that more people haven’t tried to get away from the arbitrary conventions of late-night talk shows. Why has the genre had so little innovation?

Some of the conventions look arbitrary but they’re not. The lifeblood of these shows, for a long time, was promotion. So you bring a guest out, you have them lit so they look attractive, in front of a backdrop that gives some depth, and with a set that makes it easy for them to talk to a host about what they’re promoting. Those factors mean things are going to look a certain way. But for me, if something is reliably irritating you need to stop doing it. There are days when I feel the machine aspect of things: first guest, second guest, music. First guest, second guest, comic.

How much of the rigidity of talk-show conventions are about network executives being afraid of change?

This is related to the idea of change: I’ve always been fascinated by Hans Gruber in Die Hard. He is so committed to his plan. He’s been working on it for years and has everything planned down to the millisecond. Then he learns that there’s a super-cop loose in the building. And that cop has stolen the blasting charges Hans Gruber needs to open the safe, he’s killing Gruber’s best men, and there’s no way he can quickly be found. Hans Gruber’s response to that information is, “Interesting. Proceed with the plan.” That was the time to say, “Everybody get your shit. We’re going back to Germany to figure out another Japanese bank to rob.” But nope. Even at the end of the movie when Hans Gruber is falling off the building and has seven seconds of life left, instead of reflecting on what it all meant, he takes out his gun and is firing up at Bruce Willis. Sometimes my experience with executives is as if they’re Hans Gruber and the internet is Bruce Willis. “Did you see that the bottom has fallen out of ads?” “Yes, interesting. Anyway, let’s move forward on a variety show with the Osmonds. We’ll get Dove soap to underwrite it!”

How does the fact that millions more people will often watch a chunk of Conan rather than the whole episode change the way you build the new show?

The thing is, I’ve got 16-year-old fans that stop me and go on about Clueless Gamer. The fact that my show will be half as long is going to mean nothing to those teenagers — even though I want to explain to them, “I’m 78 years old and I’ve been doing this for a long time! I fought in the Korean War, you punk!” But the important thing is to make the stuff. Then we figure out what goes on the show, what goes directly online, what is put out as a caffeinated drink, what becomes a saline solution that goes in your eye.

Do you enjoy figuring that part out?

I do. Whenever I find myself becoming cranky about these kids today I stick my face in a microwave and put it on roast, because being cranky is the easy way out. Most of the shift to the digital world has been happy for me. What saved my ass in 2010 after the Tonight Show situation was this grassroots internet thing that I hadn’t known existed. And younger generations that don’t care about the traditional talk-show format have made my job more fun and made my connection to certain viewers more intense. There are people that deep dive just on our Jordan Schlansky videos. Some of those people have tattoos of him. I don’t think that would’ve happened if the viewership was still just about, “I catch Conan once in a while at 11.”

I can’t imagine Jordan Schlansky, with his bizarrely pristine temple of a body, would be happy about anyone getting a tattoo in his honor.

Well, he’s an egomaniac so he’d be flattered.

Do you have theories about why the Schlansky stuff does so well online?

All my best remote stuff involves me getting into awkward situations with somebody else and then having that play out in an honest way. And Jordan Schlansky is this very Spock-like presence; I have a fascinating chemistry with him. I’m very aware when there’s good comedic chemistry between me and someone else, whether it’s the guy behind the counter at the sandwich shop making my turkey melt or …

A journalist maybe? Would that ever happen?

In theory, yes. Not with you. With Jordan though, there’s a very non-manufactured feel to the interactions. It plays so honestly because it’s clearly not been ruthlessly engineered in the way that TV often feels. And maybe the quiet, slow-burn aspect of it is a nice reaction to other comedy, which I think in general has sped up over the years.

What about on the business side: Have you heard any good ideas for how to address the fact that your online material can get 50 million views but doesn’t make as much money as your show, which is viewed by fewer people?

I’d love to pretend that I’ve cracked it. But maybe this is an example: It was a happy accident when video-game companies started saying, “Hey Conan, we’re the number-one video game. Could you review us? We’ll pay for it and we’ll pay the talent and that money will go into your show coffers as advertising.” And I said, “You don’t understand. I’m bad at video games, I’m contemptuous of them, and I’m going to shit all over yours.” But it doesn’t matter to these giant companies. They invest a billion dollars in games that take nine years to make and then they roll out Oculus Nine: The Becoming — where you pretend that shards of glass are put in your skull and you become who you used to be in another dimension and you get to watch your SAT scores fall — and I am part of the business model for that. Because I’m not respected as a gamer, these companies seek me out.

It makes no sense.

It’s a perfect have-your-cake-and-eat-it-too situation for me. It’s like if I were doing these things for Ford, I’d be saying, “The new Ford Explorer blows. I wouldn’t buy it if I were you.” And they’d say, “Thank you, Conan, and here’s a check that’ll pay for more weird sketches involving a moose in the audience.” “Thank you, heartless company!”

What exactly did you mean when you said the internet saved your ass in 2010?

For years I would do Late Night and feel like I was on submarine duty. You’d get signs that people liked what you did, but mostly you were submerged underwater doing the show. But when the whole Tonight Show thing went down in 2010, there was this explosion of visible support on the internet. It even got back to me that NBC thought I was orchestrating all this grassroots online support, which I wouldn’t have known how to do. So the thing that saved me was seeing this emotional connection I had with my fan base. It took me by surprise. And so did how people responded to what I was doing on Twitter. That all kept a connection alive with my fans when I was out of a job, and by the time I relaunched on TBS the online following had become a strong part of my identity. Since then, I’ve been very interested in any technological advance that can enable me to further get into people’s faces and irritate them against their will.

You’ve got something like 30 million Twitter followers. How valuable is that to TBS?

It’s very much a factor in them realizing that we’re onto something in the way we approach the online world. I don’t pretend to know where media is going but I do have a hunch that a different kind of late-night show will work best in 2019. I want to be more agile. I don’t want to be a cruise ship. I want to be a cigarette boat pirouetting around. Maybe in five years you’ll look at what I’ve done and say I was wrong. And then you and I will strip to the waist and fight about it.

Or not. We don’t need to fight.

Well, for me, the wrestling would be more of an erotic thing. But clearly, the ad dollars are going online and we’re figuring out more ways to monetize what we do there. So whatever online presence I have is definitely valuable to TBS. Frankly, I don’t know where I’d be without it.

Just to go back to the situation with The Tonight Show. Eight years later, do you have any more sympathy for NBC or Jeff Zucker or Jay Leno? How does that all look to you today?

I have a good perspective on how it happened. There were executives on the brink of a corporate merger, and they were scared and wanted to have all their options. It could have been handled a lot better, but I decided a long time ago that I wasn’t going to waste time being angry. With very few exceptions, I tried not to take any of it personally.

But what’d you take personally?

Without getting into specifics, there were a few people who I felt were not being good human beings. But I see that what happened was an inevitable clusterfuck. I had a bad feeling the minute NBC said, “You’re going to go do The Tonight Show but Jay’s also going to be on at 10 doing a Tonight Show before your Tonight Show.” It’s like when the Bachelor can’t decide: All three of us were not going to fit in that hot tub.

Is there any part of you that thinks maybe you leaned too hard into the victim role back then?

Right, these were the definition of rich white people problems. All I can say is that I was discombobulated by the whole thing. I remember at the time thinking that when Dave [Letterman] had his thing with Jay Leno, he was allowed to keep making jokes about it for five years. And when we made jokes about my situation, people interpreted it as real rage. That surprised me. When I saw that people were taking the jokes as my real feelings, I decided, Let’s just not talk about this at all.

But putting aside other people’s interpretations of your behavior, how long did it take you to process what happened with The Tonight Show?

I had some PTSD for a while, because I always took my job seriously and tried to be an honorable person, and then to have that outcome with The Tonight Show confused the shit out of me. Then you realize, Oh, everybody has bad work situations. You move on. I’m much happier now than I was in 2010 and 2011.

Conan O’Brien. Photo: Bobby Doherty/New York Magazine

I know you have reverence for late night as an institution, but do you believe generally that people under the age of, say, 35, care about the late-night talk show as a thing?

I’m not sure. Millennials can really like a single comedy bit, but late night as a whole used to offer something that you couldn’t get anywhere else. If you say “Johnny Carson” to me, I think about watching with my dad. There’s an emotional connection there for me. Then Letterman came along when I was a senior in high school and blew my mind. He was like Cortés finding the Pacific. Please check that. He was like Cortés finding that thing Cortés found. But you had a very specific relationship to late-night hosts. I meet people in their 40s who say, “You got me through high school.” I hug those people — sometimes a little too long. But I hug those people because I remembered making the show in the ’90s and feeling that I was writing messages in a bottle from my little raft on late night and throwing them into the ocean to see if they’d reach anyone. That kind of connection is not really there anymore.

I remember very clearly the experience of being 12 or 13 years old and watching you on Late Night at 12:35 with the lights off and the volume low because I didn’t want my parents to know I was still awake. The viewing experience was this intimate thing — even if the thing itself was about a masturbating bear.

Yeah, the thing was, back then if you missed us you missed us. And we would do these strange things. I remember Andy [Richter] and I did a bit where I said, “Andy, it’s time we did an old number.” And he went, “Yeah, it’s time for an old number.” Then he and I sang Led Zeppelin’s “Dazed and Confused.” Just like in The Song Remains the Same, we cut these cheesy fantasy segments into the song — one of them was George Plimpton and I battling each other in suits of armor. Then about a week after that aired, I’m in the Village and I go into a bookstore. There was a guy with a scruffy beard working there. I went to pay and he puts his hand on mine and says, “Hey man, I saw it. I saw it.” “You saw what?” “The Zeppelin thing, man. I fucking saw it.” Having this communion with one guy down on Houston Street made me feel like I’d done my job.

Do I Know You? Conan and Andy Find Out

Before you got The Tonight Show there was the idea kicking around that the comedy you did for the 12:35 audience might not work for the 11:35 audience. Did that idea ever make any sense to you?

No, it always seemed arbitrary. Especially in the lead-up to doing The Tonight Show there was so much overthinking by the media. I remember someone wrote, “He’s too tall.” Someone else said, “He’s too smart.” Trust me, I’m not, and I don’t even know what that means. All I’ve ever known is that if someone doesn’t like what I do, I can’t help them. I couldn’t change what I do if I tried. I’m like a serial killer: If you don’t stop me, I’m going to keep doing it.

People also used to point out — especially in the early days of Late Night — that your comedy was more abstract than other late-night hosts. Was it at all interesting to learn how critics saw you as being different from your competition?

If I’d read all the speculation before I started in 1993, I’d have shot myself. I wouldn’t have been able to do the show. But I was always really tickled that the stuff that horrified people in ’93 was the stuff they liked in ’97. Because we did a bunch of that material in the first two weeks we were on the air: In the Year 2000, Actual Items. I did get better at my job over the years, but I didn’t transform into a different human being.

Who else in late night is doing particularly good work right now?

One of the funniest people on TV is Nathan Fielder. I know [Nathan for You] is not a late-night show. He came on my show not that long ago and brought Susan Sarandon as a backup guest in case he didn’t have his good stuff. She sat down and didn’t say anything. Then at some point I leaned over and said, “So, Susan …” and Nathan’s like, “What the fuck? I thought I was doing pretty well.” I love a guest who comes in with a strong conceptual bit like that. Will Ferrell was great for those. He did a bit once where he was talking to me, completely straight, and then about six minutes into the interview he pulls back his jacket and you can see he’s got a gun. Then we got into a fight that led to us both grabbing for the gun and it going off. I love pure silliness like that. But it’s tough now because Trump has so upset everyone’s comedy Geiger counter.

He’s the shadow hanging over late night.

He’s a very tricky subject. I don’t know how much of the comedy on Trump will seem funny in five years. But I’m sorry, you asked me a second ago about late night and I immediately got into Nathan Fielder. I think that’s because —

You’re actually very competitive and don’t want to praise the other hosts?

Because my all competition is better than me in every single way.

I have some questions about your pre-hosting career. You were writing for Saturday Night Live during one of the show’s real golden ages. Which cast member was the most fun to write for?

That’s a hard question because I was there for Jon Lovitz, Dana Carvey, Kevin Nealon, Victoria Jackson, Jan Hooks. But maybe Phil Hartman was my all-time favorite person to write for. He was the only comedic performer I know who could convincingly be a street punk or a 65-year-old father in slacks or an escaped convict or Frankenstein or an unfrozen caveman lawyer. To see him commit to a character the way he would was magical. I don’t know that Saturday Night Live has ever had a better utility player than Phil Hartman.

Another this-is-your-comedy-life question: What’d you learn from James L. Brooks while you were a writer on The Simpsons?

The thing is, when I got to The Simpsons, I thought of myself as the comedic version of Tom Cruise’s Maverick from Top Gun.

Wouldn’t that make you Goose?

Congratulations, you have turned my wonderful analogy absurd by stretching it out by a fraction of an inch. That’s something you can do to any of my jokes by the way. But when I got to The Simpsons, I wanted to be a hotshot joke writer. I had contempt for people who would say, “What’s the emotional truth of this scene?” “Fuck that! You want emotional truth? Go work on The John Larroquette Show.” That’s a good reference. Anyway, James L. Brooks said that yes, the jokes have to be good, but you also had to have the sensibility of writing for a family who loves each other. I saw that the stuff I was interested in — like Springfield getting a monorail — was just a bunch of random Lego pieces if they weren’t tethered to the characters of the Simpson family. Believing in the emotional reality of that family not only didn’t hurt the jokes, it gave them more power. Writing comedy like that isn’t my forte, by the way. I’m much more suited to abstract ideas.

I realize that earlier, when I was asking about whether younger audiences have reverence for late night, I assumed that you still do. Was that a correct assumption?

It’s harder as you get older. When I was a kid and visited New York I was in awe of the Empire State Building. Now it looks like a big piece of shit to me. No, I’m kidding. It’s beautiful. But as a late-night host, you have reverence for upperclassmen, contempt for yourself, and then anyone that follows you, it’s like asking Lauren Bacall, “Don’t you think that that 21-year-old bombshell is hot?” I’m over here with a long cigarette ash going, “That goddamn bitch!” But that’s not who I want to be. I have reverence for anyone who makes the form their own. And I have reverence for that because late-night talk shows are a uniquely American art form. Yes, fuck it; I’m saying that late-night talk shows are an art form. “When done correctly,” said the snide O’Brien in between sips of fine wine and Diet Coke.

You’re the longest-running host in late night, and you’ve got ten years on Kimmel. But you’ll probably always feel to me like the younger alternative to Jay and Dave. When did you stop seeing yourself as occupying that position?

What’s crazy is how quickly my position flipped. For 12 years when I’d walk into a restaurant younger people would be excited but older people would look over and sneer: “The nerve of that young punk with his hair and his masturbating bear!” But the minute Jay and Dave were gone it became, “Of all the people with microphones, you, Conan, are the one closest to death.”

That said, do you think about hanging it up?

Yeah, I do, but maybe not in the expected ways. When Johnny Carson retired it cemented into everyone’s head what that’s supposed to look like: Johnny said “Good-bye, America,” and America said, “Good-bye, Johnny,” and then we all cried as he went up an escalator into the sun to become an eternal Aztec warrior. Then when Letterman went off the air, again it was, “Good-bye, America,” and we all cried as he went up an escalator into the sun to become the four-handed Vishnu god.

Only to come back.

Yeah, two years go by and Letterman’s like, “I’m just going to go do Netflix.” And when I saw he was coming back I thought, of course. As there are more media options, each individual thing becomes less important. So in the modern television world there’s no reason why, when you’re done with one show, that you have to say, “Farewell, all,” and get on a winged horse and be taken up into the stars.

You’ve got these metaphors down.

I wasn’t done: And then as you and your winged horse reach the stars you become the stars themselves and on a clear night you can see me up there in the cosmos but you’ll never touch me again. Now I’ve used up my metaphors and we can move on.

I’ve talked with Letterman and Jimmy Kimmel and now you, and you’ve all spoken about how interviewing boring guests is a part of your job that feels like a real grind. Why is doing that such a pain in the ass?

Here’s the perpetual conflict: These celebrities come on my show to promote something. And my job is to keep them, for as long as possible, from mentioning that project. That is my purpose. That is my religion. But there are guests that are determined to only talk about their project and to do it devoid of humor. When that kind of guest is on, we are in a fight to the death.

Can you play that fight out for me?

Let’s say the guest’s movie is called The Cornelius Effect. They’ll go, “I want to talk to you about The Cornelius Effect because …” “We’ll get to that in a second. I talked to your doctor. He said three weeks ago you had a colonoscopy — and we’ve got the footage.” “Okay, but The Cornelius Effect is … ” “We’ll get to that, but first I want you to tell the story about the time your head got stuck in a toilet.” Then, eventually, I’ll say, “Okay, let’s talk about The Cornelius Effect. You know what I loved about The Cornelius Effect? When I went to see it there was some gum on the floor that I thought was fresh gum and I ate it. It turns out now I have syphilis.” Then the guest will say, “Now can I talk about The Cornelius Effect?” “I’m sorry, we only have time for a clip.”

But you never quite did the Letterman thing where you were actively hostile to a guest who bothered you.

I’d like to tell you it’s a moral choice, but the truth is that I just wasn’t as good at that as he was. I was once on Letterman and he asked me about my hosting pet peeves. I said, “When a guest comes out and stands for too long before sitting down. You know, like, a Wayne Newton might.” I just threw that name out there in the moment. Then two days later, Wayne Newton sends me a telegram: “I thought better of you, Conan.” I was really upset that I’d been rude. I wrote him a letter and apologized.

So you don’t want to be rude, but if Norm Macdonald is rude to Courtney Thorne-Smith on your show, so be it?

[Laughs.] But the difference is that Norm Macdonald is not sweating it!

Rude or not, it’s one of the funniest talk-show exchanges of all time.

Yeah, and not only is Norm not sweating it, he doesn’t remember it even happened. I’ve always said to my wife: If there were an operation that cauterized the part of the brain that cares what other people think, I would have that operation. If the doctors said, “The operation means you will also have no control over when you urinate and your urine will have a foul smell forever,” I would say “toast it.”

What part of you would your wife say needs to be burned off?

My wife’s said to me, “You worry about things you don’t need to worry about, and then when terrifying things are happening, you’re never worried.” It’s weird. I’m more afraid of failing to make an audience laugh than I am about getting shot in the hip with a high-powered rifle. Now other people would say, “That’s because you’ve never been shot in the hip with a high-powered rifle.” And I would say, “That’s because you haven’t been in front of a roomful of people you were supposed to make laugh and failed to make them laugh.”

Does the conflict you described between you and guests ever occur with musicians who appear on the show? For some reason I’ve never forgotten seeing Pete Townshend come out on Late Night with an acoustic guitar and expecting him to do “Behind Blue Eyes” and he does a cover of “Barefootin’” instead. Did nobody nudge him to play a different song?

I don’t remember that specifically, but I had a similar experience in college. I loved Smokey Robinson, and a friend of mine and I got in a car and drove out to Western Massachusetts to see him. We get to the show and Smokey Robinson came out and did every single hit he ever had as one medley that lasted three minutes. When he was done, he said, “And now the rest of my concert will be devoted to my album Touch the Sky.” At that point my ocular jelly melted out of my skull, went into my mouth and poisoned me. But let me tell you one the greatest things in my life. It’s top three; the birth of my children are not in the top three.

Top Ten?

No, and Letterman owns Top Ten, so don’t say that to me. But I’m a big Brian Setzer fan, and there was one time he came on Late Night with his entire orchestra and I came down for the run-through. He saw me sitting in the empty Studio 6A and went, “Hey Conan. How’s it going, man? Anything you want us to play?” I’d heard that he did the most amazing version of the Hawaii Five-O theme song. So I’m sitting there like a dick, like Cecil B. DeMille checking out chorus girls, and I say, “How about Hawaii Five-O?” And they go into it with all the modulations and the riffs. It’s incredible that I got to hear that. I also sat down for the run-through when Brian Wilson from the Beach Boys was on and he was like, “Hey man, anything you want to hear?” “Sloop John B.” “Hit it, guys!” I have my flaws, but I don’t take that experience for granted.

That you were able to reduce the great Brian Wilson to a human jukebox?

To a human Siri. Yes, exactly. Then I made him get me a latte, but I said he also had to make it himself, and when he did, it wasn’t very good so I made him do it over again. But no, if someone came in here and said, “Times up, Conan. It’s over. You’re done,” I would be amazed that I got to do this.

I know one’s innate sense of humor isn’t really something that ebbs and flows, but have there been any changes in comedy generally, and not just in late night, that affected what you do?

The biggest shift in comedy is that there’s more good stuff now than ever. It used to be that things as funny as Letterman or SCTV were shocking because it was so rare to see comedy that good. Now you can’t keep up with it all. Atlanta blew me away and I still have to see the new season. You can also get away with more. Simon Rich did this sketch on his show about a guy who broke up with his girlfriend and then he sees that she’s dating a 110-year-old Hitler. That’s a sketch that would never have been allowed to make it to air 30 years ago.

The space for what’s possible has gotten so much bigger.

It’s infinite. And all of us comedians are competing against the billion people on YouTube. Today a 15-year-old girl in Duluth will come up with a perfect idea and it’ll have a cat in it and she’ll film it perfectly and it’ll be the funniest thing. Comedy now is about the funniest person today. “Hey Conan, it’s not you. It’s a 15-year-old girl in Duluth.” And I just think, Okay, she wins. I don’t think, But I’m the oldest man in late night! I’m the last man with a pompadour — a haircut not seen since 1948! Don’t I get comedy points for that? No, fuck you, Conan, you don’t. The kid wins. That’s how it should be. It’s humbling how goddamn funny people are.

This interview has been edited and condensed from two conversations.

Annotations by Matt Stieb.