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Conan O’Brien is sixty-two, and he has done, more or less, everything in modern American comedy. President of the Harvard Lampoon. Writer for “Saturday Night Live” and then “The Simpsons.” “Late Night,” starting in 1993. The whole controversy with Jay Leno and the “Tonight Show,” in late 2009. “Conan,” on TBS. A long career in standup. Podcasting. Back in the day, he was a drummer in the Bad Clams. Not a good band, but O’Brien did become a pretty decent guitar player, as you can hear in his performance, with Jack White, of the Eddie Cochran classic “Twenty Flight Rock.”

Lately, he has been preparing to host the ninety-eighth Academy Awards, which will air on March 15th. It is, arguably, the biggest gig in comedy, and, last year, O’Brien pulled it off with his usual sense of knowing self-deprecation. As he kicked off the show, he started striding back and forth, saying, “I am walking to show I have control of the stage.”

Last year, the Oscars were preceded by Donald Trump’s return to the Presidency and the wildfires in Los Angeles; this year, the weather is, arguably, darker. How will O’Brien find a way to provide a mental break for a weary nation? Recently, I spoke with O’Brien, who had taken a break from his writer’s room, about the diminishing relevance of late-night TV, the hilarious story of the death of his parents, and the loss of his close friends Rob and Michele Reiner. Our conversation for The New Yorker Radio Hour has been edited for length and clarity.

Have you started writing and rehearsing for the Oscars?

Yeah, I started writing a while ago. Ideas are like R.A.F. pilots in 1940. You have to generate a lot of them. A lot of them fall by the wayside and then some endure. And so we’ve been going for a while. We’ve got a great writers’ room, and I’ve already started going to clubs to try out material, which is really fun. It’s good to keep you in shape or get you ready.

It’s a high-risk, maybe even low-reward, gig, isn’t it?

I choose not to see it that way.

But you killed!

Yeah, it was really fun. I mean, I grew up watching Bob Hope do it, Johnny Carson do it. So it’s a very cool thing to be connected to. As you know, I’m very interested in history, and this thing has been around for a hundred years—almost a hundred years—so let’s have fun with it, is my attitude.

Anybody give you good tips? Billy Crystal, or anybody else, on how to deal with an audience—I don’t even know how big that audience is now.

No one’s pulled me aside and said, “O. K., here’s the secret—”

Smile.

Yeah, exactly. But what I’ve learned myself over time is that I can’t fake enjoyment. I need to find ways to make sure that I’m having a lot of fun. I need to prepare—I mean, I’m a big preparation person. I work with this brilliant team of writers who are just downstairs from where I’m doing this podcast, and they’re cranking away, and it’s kind of . . . it looks like they’re working on the Glengarry leads. I go down there and they’re all around a long table. . . . “These premises are no good. Yeah, these premises are no good. We gotta get the Glengarry premises.” And I yell at them. I’m the Alec Baldwin who comes in, gives that great speech up front. I’m talking about the movie now. I think we all know that. Not the play.

Where does politics play a role in the way you’re thinking about that kind of night?

It’s tricky. I’ve done political comedy over the years, certainly. I’ve done two White House Correspondents’ dinners. On late night, we used to do lots of political comedy. We’d do it on the TBS show as well. It’s never been in the front of my comedy brain. I don’t think it’s what drives me. I, for better or worse, have a brain that scrambles things, loves cartoon imagery. I am probably as influenced by old movies or literature as I am by, frankly, Warner Bros. cartoons. And it all gets mixed around in my head. It’s very impulsive. I don’t know where my sense of humor comes from, but I know that, when I do political comedy or I make a political joke, it has to really resonate with me. And I can’t tell you what that is, but it has to feel true to my comedic voice or it feels hollow.

Does Trump feel funny to you anymore?

No. I mean, I’ve talked a little bit about this, and I’ve said I think he’s bad for comedy.

What does that mean?

Well, years ago, when I was at Harvard and working on the Lampoon, we would try and think of magazines we could do a parody of. And there was one magazine we always knew we couldn’t parody, which was the National Enquirer. If a magazine has, as its cover, “Elvis Still Alive, Marries Alien and They Have a Baby That’s a Three-Speed Blender”—if that’s what the real magazine’s coming out with, you can’t do a comedic take on that. It’s very difficult, or I think impossible, to do. And I think Trump—if he were a magazine, it’s the National Enquirer. There’s a lot that’s so bombastic and so outrageous and so unprecedented that how do you—“Oh, I’ve got a great Trump impression, and I have him saying this.” Well, that’s not crazier than what really happened yesterday. So I don’t know how this is funny. Does that make sense?

Yes. But, when you watch the cold opens for “Saturday Night Live,” or Jon Stewart on Monday night, or Trevor Noah at the Grammys—I think he even inspired Trump to threaten to sue him.

Guess what, David? That’s not a hard thing to do.

No, I know.

We could do it right now if you want.

I’m involved in a lawsuit right now.

I’m sure you are!

You wouldn’t believe it.

Yeah. Like I say, “S.N.L.”—they’re crazy talented. Jon Stewart, crazy talented. These are all really good people who do that extraordinarily well. When people talk to me about it, I say, Well, all I can do is come out of my own personal experience, which is: this isn’t inspiring a lot of chuckles for me.

Now, there’s a different thing—there are comedians who, when they talk about Trump, quickly get very angry. And I’ve said this before, but I think it’s possible to surrender your best weapon. Your best weapon is to be funny. And if it just evolves into name-calling. . . . I mean, I am all for people trying. And, when there’s a really good joke about the President or the Administration, if there’s a joke about the right or the left and it’s a good one, I’m elated. I just think that in the current climate, things have gotten so stretched out—think about that Dalí melted watch—that it’s hard to find purchase.

Where does the network get involved?

There’s always some issues. I’ve been dealing with networks for most of my life. So there’ll be stuff. And then that’s when you roll up your sleeves and you start arguing back. And it can be—

Do you win?

Yeah. Oh, yeah. You can win. You can also lose.

But on what basis? Are there rules, or is it just human persuasion?

Certainly there are rules about what can be said and what can’t be said. The Academy has rules. I mean, everyone has rules.

Once you’ve lived in New York for a period of time, you come to this awareness that, oh, everything ultimately is a New York co-op. They have their rules. You can say, “Hey, but on this other awards show I got to do this.” Let’s say I’m living at—I’m going to make it up—I’m living at 172 West Eighty-ninth Street. They’ll say, “This is the Drake Building. And you live here at the Drake Building.”

“Yes, yes I do. What I’d like to do is put in my kitchen window . . .”

“No, no, no, no, no. We don’t let people alter the windows here at the Drake.”

And you’ll say, “Oh, O.K. Well, it’s funny, when I lived over at the Macklemore . . .”

And they’ll say, “Yes, we know. That’s the Macklemore.” And suddenly—

It’s O.K. for Nikki Glaser and Ricky Gervais at the Golden Globes.

Yeah. I’ll say, “Well, I once did the People’s Choice Awards, and—”

And they’ll say, “Oh, yes. Oh, we know. That’s the People’s Choice Awards—they don’t have standards. Their windows and their kitchens are horrid. You are now . . .”

And so it’s not just the Oscars. Every show probably feels that way about the other shows.

Ever since the Will Smith incident, the slapping incident—and, when we were kids, you had the streaker incident. Do you worry about the kind of unplanned disaster happening?

No. Well, you know, I don’t want anyone to slap me—

But you’d like a streaker.

I’d like a streaker. And you know what I’d really like? A streaker to slap me.

That would send you.

That would just satisfy so many of my dormant Catholic hangups.

But it’s a weird duality here. It’s a weird thing. I like to plan, and I like to prepare. And then I love it when something goes off the rails.

Give me an example in performance.

Oh, just for years and years doing my show. If, accidentally, a light falls, you can make a whole show about that. Do you know what I mean? I don’t know what it is about human beings, but they instinctively know when something is real and of the moment. And then when they see you react in real time like a human being and make something funny out of it, that has ten times the value of anything you could’ve written. So you have to be open for things to slightly go wrong, and it’s fun and electrifying.

My whole life has been: prepare, but then, like any good quarterback, be ready for the whole play to fall apart, and then wing it.

Scramble.

Scramble. And that’s a beautiful thing.

Do you do that, too, as a comedian? To what degree are you—you’re not like you are at home, or at dinner. You’re a heightened “you.” There’s a performance aspect to it.

It’s so funny you say this—I’m always this guy. There is a heightened me, but it’s really not that much different. I routinely will just talk to people on the street, complete strangers, and then that will lead to me doing a bit, and trying to get them into it—trying to do improv with random people on the street. And I’ve been maced.

Yeah, I can imagine.

Yeah. It’s unwanted improv. But it’s not that different. Yes, there’s a heightened me, and there’s a depressed me that just wants to crawl in a corner and read a book, but I have access to this guy a frightening amount of the time.

It doesn’t have to be summoned or forced into being. It’s there.

I think it’s glandular. I mean, I’m joking, but I’m also not joking. My father, who was a very smart man and very analytical and a scientist, was looking at me once—and he watched every late-night show—and he said, “Oh, I see, I see. You’re making a living off of something that should probably be treated.”

And he wasn’t joking. He said, “I see your synapses and the rhythm of your circulatory system . . . and then you found a way to be compensated. I see.” And I thought, Thanks, Dad.

From what I understand, you also treated the death of your parents, in some way, comedically, therapeutically, humanly. I wonder if you could tell that story.

I was in Austria when I got the word that my father had passed. I took a van to another van to the airport, got on a flight, got on another connecting flight, made it back to Boston. And you go through all the intensity of that.

And then there was a moment where I was just outside my house—my family house, the house I grew up in in Brookline. And I got this lovely text from Will Arnett, and he said, you know, “We’re all thinking about you. We’ve all heard the news.” He does the podcast with Jason Bateman and Sean [Hayes]. Whenever we’re together, we always just joke about Bateman, because that’s just what you do. It’s like the show-biz thing. And, if I’m with Bateman, we joke about Will Arnett.

But so, I get this lovely thing from Will Arnett. And I just wrote back, “I blame Bateman.”

And then he wrote, “Oh, I guess we all have our coping mechanisms for . . .” And I cut him off and say, “Jason Bateman killed my father.” Which is insane.

But it’s—make of it what you will. That’s what I said.

I think your father had it right. I think he had it absolutely right.

Exactly. My father had it right. Somewhere, a ghostly father was perched on my shoulder saying, “Yes, yes, this is it. See?”

So the story gets more remarkable because, three days later, my mother passed, in the same room that my father had passed in, which was really shocking. And I’ve laid out now that I have space for comedy still. So Will texted me after a little time had passed, and he said, “If you want, I could have Bateman take care of your sister.” And I immediately texted back, “3053 Beacon Street, Apartment 17F. Make it look like a robbery.” Because I knew my sister Kate—she would find it funny. And so he read all that on the air [on his podcast], and people were just, like, Oh, my God. And it kind of went viral.

And that is how I communicate. I’m a whale. He’s a whale. We make these weird noises at each other. That’s how we communicate. And I know how much I love my parents, and I know what a lovely person Will Arnett is, and Jason Bateman. None of this is real, but it’s this way of doing business and connecting.

When it all came out that I had thrown Kate under the bus, she texted me and said, “You don’t think I could take Bateman?” It’s, like, very good, Kate, thank you. But that was her immediate reaction.

And the funerals hadn’t even taken place yet.

Uh, no, they hadn’t.

So I don’t know. What does it all mean? I mean, I definitely know I am a hundred-per-cent Irish.

When did you recognize this in yourself? How old were you when you started speaking whale-speak, or comedian-speak, and you recognized this inbuilt irony, whatever it is, as a way of being in the world?

Well, when you’re a kid—I think we all do this—you go through your checklist. You emerge into the world. It takes a bunch of years just to figure out what the hell is going on. And then very quickly things start to get sorted out. Am I an athlete? No, I am not an athlete. Do the girls go crazy for me? No, they do not. Am I a math whiz? No, Conan, you are not. Am I a tough guy? Oh, God, no, Conan. You are not. And it’s a lot of nos.

And then I hit this thing where I would make people laugh in class. I wasn’t the class clown—I was very quiet, but I would make friends laugh, and I started writing little plays and putting myself in them, and they were funny. And then, in creative-writing classes or in English class, I would write funny stories. The teacher would have me read them, and everybody would be laughing, because I’d put a lot of comedy in there.

So what happens is that you realize that there’s this one arrow in my quiver. There aren’t thirty-five arrows—there’s one. So I probably started working this comedy thing, unconsciously, in 1972 or 1973, in Brookline, Massachusetts, in a playground. And then you’re just working it and working it. And then I started seeing things on television or in the movie theatre. And you’re learning about rhythm, just learning about rhythm and what’s funny, and why is that funny? And I never got too analytical about it. That’s like the part of the map that disappears and there are dragons there. Like, don’t get into analyzing it. Just what’s funny, what’s not funny.

Let me ask you about late-night TV. The big news about late night this past year was Jimmy Kimmel and Trump and all that. But I think we can agree that what’s happening over time is that the whole late-night scene, and especially being watched in real time—that’s collapsed, or it’s in the process of collapsing.

Yeah.

How much do you care that it’s collapsing?

Well, there’s the sentimental side of me that grew up watching Carson that liked that. But I have a very ingrained wariness of sentimentality. But, when I sort of Google Earth out of the whole thing and try to look at the whole picture, I realize that things are constantly changing. Look at all the things that are changing all the time.

And so people are saying, This is tragic, and you’re, like, Well. . . . I’ve said this to Stephen [Colbert]—

Is Stephen treating it as a tragedy, or what?

Well, I think Stephen very rightly is—

Pissed.

Yeah, he’s pissed, I think rightly, but . . . he’s got a big staff and cares about those people. I’ve been in that situation, and that is excruciating. And so I think he has all the appropriate feelings. What I’ve tried to tell him is that there’s so much of this that doesn’t have anything to do with you. These giant glacial plates are moving, and you are doing the best you can, and you’re such a talented guy, and he’s done an amazing job. And, yeah, there is definitely a thumb on the scale. We all saw that, with Jimmy Kimmel, with the F.C.C.—that was just outrageous and wrong.

But in the larger picture, when you look worldwide and see voices being silenced, they really get silenced. I don’t think that’s going to happen with Jimmy Kimmel, or Stephen Colbert, or anyone who’s doing a late-night show.

And you found a way.

Yeah. I left my late-night show four years ago. I’ve had a wonderful time. I think I reach more people now, either through the podcast or doing the travel show. I have all this freedom to be me in different ways, in different formats. There’s a lot of really beautiful opportunities, and I’ve been having a blast and getting to have types of interviews I never could have had in that old “you’re up in the attic” format.

Like Robert Caro.

Yeah, I can talk to Robert Caro for an hour and a half, and then talk to Al Pacino, but then talk to Charlie XCX for an hour. I mean, this old format is going away, but they’re being replaced by a multitude of other ways to connect with people and be funny, and be satirical, and be probing, and let your talent run wild—that in some ways are more freeing.

And you can be master of your own destiny. You’re not working for, ultimately, a giant toothpaste company or whoever it is who owns your studio. So, again, I find myself trying to be optimistic in these situations.

Conan, we’re about the same age, and we’ve reached the age where, if one of our contemporaries dies, it’s incredibly sad, but it’s not an absolute shock. It’s not a tragedy in the sense of when we were much younger, if somebody died in an accident or of a disease or something. You had something happen this year to two friends who had been guests at your house the night before, the Reiners. Can you talk a little bit about your experience of that horrific tragedy?

I knew Rob and Michele, and then increasingly got closer and closer to them, and I was seeing them a lot. My wife and I were seeing them a lot, and they were so—they were just such lovely people. And to have that experience of saying good night to somebody and having them leave and then find out the next day that they’re gone. . . . I think I was in shock for quite a while afterward. I mean, there’s no other word for it. It’s just very—it’s so awful. It’s just so awful. And I think about how Rob felt about things that are happening in the country, how involved he was, how much he put himself out there—and to have that voice go quiet in an instant is still hard for me to comprehend.

I watched that Mel Brooks documentary that Judd Apatow did—it’s terrific. And there’s Carl Reiner, and they have such a close relationship when they were both in their nineties, I guess, until Carl died. And then Rob Reiner pops up in this, and he seems relatively young and so vibrant and alive. And to have that in the back of your mind as you watch this film—for me it’s tragic. For you, it must be—it’s incomprehensible.

These people are so larger than life, especially if you’ve grown up watching them or appreciating their work. I mean, I just keep mulling over . . . the body of work, I think it’s seven movies that Rob Reiner made, in quick succession, that are classics. Now, if you can make one great movie, that’s impressive. It’s an almost impossible feat. To make two means that you’re one of the greats. To make seven—in, like, a nine-year, ten-year, eleven-year period—is insanity. With “Spinal Tap” alone, if that’d been the only thing he ever did, he influenced my generation enormously. “Spinal Tap”—when it came out, I was in college, and it was like a splitting-the-atom moment. You have those moments where you see something truly remarkable.

And another person I’d put in that category: we just lost Catherine O’Hara, which is incomprehensible. And that’s someone who was perfection. And we’ve all had that feeling where someone’s being eulogized and we’re thinking, They were good, but this person’s kind of laying it on thick. Catherine is just—who’s a funnier performer than Catherine O’Hara? And what people didn’t get to experience personally was, she is—she was, I’m still saying “is”—she’s possibly the nicest person I’ve ever met. Just glowed, and good will. . . .

But here I am on a podcast talking like this is unusual. This is what we’re all contending with. It is something you don’t think about—if you’re lucky, you don’t think about it for the first couple of decades of your life—and then it’s people saying, “Did you hear?” And you walk around concussed for a week. So that’s what it is now, I guess.

Well, I was in a good mood when I got on this podcast.

How are you feeling now?

And you’ve taken me—this is the worst. I mean, this is a colonoscopy right now, and there has been no propofol.

“See you again in five years.” That’s the best thing you can hear at the end.

Or “You didn’t use the right camera.”

Sorry. We’re going to have to do it again.

You used a 1955 Hasselblad. You jammed it up there.

Yeah. Slowly, slowly. Conan O’Brien, thank you. ♦