Conan O’Brien on What Can Go Wrong at the Oscars

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0:27This is the New Yorker Radio Hour, a co-production of WNYC Studios and The New Yorker. Welcome to the New Yorker Radio Hour. I'm David Remnick. Please welcome four-time Oscar viewer, Conan O 'Brien.

0:46Hosting the Academy Awards is not an easy gig. Everybody delights in panning it. It's always endlessly long. And it's often a parade of self-congratulation and sanctimony, and the musical numbers are Busby Berkeley on acid when they succeed. And yet, as host of the Oscars last year, Conan O 'Brien really nailed it. It's Hollywood's biggest night that starts at four in the afternoon. Everyone here just had brunch. O 'Brien's resume starts out as president of the Harvard Lampoon and goes right through writing for Saturday Night Live and The Simpsons. And then, of course, he was host of The Tonight Show.

1:29The years have gone by, and now he's one of comedy's wise elders. Ironic, self-deprecating, zany. His sensibility translated perfectly to podcasting, too, on his show Conan O 'Brien Needs a Friend. And yet you can still imagine Johnny Carson or Bob Hope delivering some of O 'Brien's best lines at last year's Academy Awards. I remember him saying during a very long show, if you're still enjoying the show, you have something called Stockholm Syndrome. And I guess we all do. And he's hosting the ceremony again in March. Have you started writing and rehearsing for the Oscars? Yeah, I started writing a while ago.

2:10And what happens is it's just ideas are like RAF 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 got a great writer's room. I've already started going to clubs to try out material, which is really fun. And it's good to keep you in shape or get you ready. Does it really help? I think it does, but I couldn't prove it to you. Having watched the Oscars - Have we started yet, by the way? Yeah, yeah, we're in. Oh, we started. Yeah. Oh, my God. None of what I just said was true.

2:49It's a high risk, maybe even low reward gig, isn't it? I mean, I think back over the years. I choose not to see it that way. But you killed. Yeah, it was really fun. I mean, I grew up, you know, watching Bob Hope do it, Johnny Carson do it. And so it's a very cool thing to be connected to. I'm, as you know, very interested in history, and this thing has been around for 100 years, and so almost 100 years. So let's have fun with it. Anybody give you some good tips, whether it's Billy Crystal or anybody else, on how to deal with an audience? I don't even know how big that audience is now. You know, no one's pulled me aside and said, okay, here's the secret.

3:35Smile. Yeah, exactly. Exactly. 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. And 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. You know, I go down there. They're all around a long table. These premises are no good. Yeah, these premises are no good. We got to get the Glengarry premises. And I yell at them.

4:20I'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 correspondence dinners on late night. We used to do lots of political comedy. We 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'm probably as influenced by old movies or literature as I am by, frankly, Warner Brothers cartoons.

5:14When 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 years ago when i was at harvard and working on the lampoon um 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 inquirer if a magazine has as its cover um elvis still alive marries alien and they have a baby that's a three-speed blender. That's what the real magazine's coming out with.

6:04You can't do a comedic take on that. It's very difficult or I think impossible to do. And I think Trump, to me, if you 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 inspired Trump to even threaten to sue him.

6:48Yeah, 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. That's the, yeah, SNL, you know, they're crazy talented. Jon Stewart, crazy talented. So these are all really good people that do that extraordinarily well. When people talk to me about it, I say, well, I have to, 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, they quickly get very angry.

7:35And 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'm 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. So I just think that in the current climate, it can be things have gotten so stretched out. Think about that Dolly melted watch that it's hard to find purchased. You know what I mean? It's hard to get a grasp on what's the straight line here. Where does the network get involved?

8:34There'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 sleeve 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. The Academy has rules about what you can do with the image of an Oscar. 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.

9:21You know, they have their rules. They have their, you know, you can say, hey, but on this other award show, I got to do this. Right. And the cup, but you're living in, let's say I'm living at, I'm going to make it up. I'm living at 172 West 89th Street. And they'll say, and it's a place called, you know, the, this is the Drake. This is the Drake building. And we're, you know, you live here at the Drake building. Yes, yes, I do. You know, what I'd like to do is put it in my kitchen window. No, no, no, no, no. We don't have, we don't let people alter the windows here at the Drake. And you'll say, oh, okay, well, you know, it's funny when I lived over at the Macklemore over.

10:12Yes, we know. That's the Macklemore. And so it's okay for Nikki Glaser and Ricky Gervais at the Golden Globes. Yeah, every award show probably is like, oh, that's fine for the people's. And I'll say, well, you know, I once did the People's Choice Awards. Oh, yes, 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, do you, and when we were kids, you had the streaker incident.

10:55Do you worry about the kind of unplanned disaster happening? No. Really? I'm someone who likes, 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 satisfy. That would just satisfy so many of my dormant Catholic hangups. It's a weird duality here. It's a weird thing. But I like to plan and I like to prepare. And then I love it when something goes off the rails. Like, for example, 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.

11:48Do you know what I mean? People, 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 is 10 times the value of anything you could have written. So you'd 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. Yeah. And that's a beautiful thing. Scramble. Do you do that too as a comedian?

12:33To what degree are you, you know, you're not like you are at home or dinner. You're a heightened you. You know what? There's a performance aspect. This is so funny you say this. I'm always this guy. I mean, 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. I'm 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 you, I think it's glandular. I think it's, I mean, I'm joking, but I'm also not joking.

13:21I think my father, who was a very smart man and very analytical and a scientist, he was looking at me once and he watched every late night show and he said, oh, I see, I see. and he wasn't making a joke. He said, I see you're making a living off of something that should probably be treated. And he wasn't joking. He said, you know, you have this, I see your synapses and the rhythm of your circulatory system and what you're doing is, and so, yes, and then you found a way to be compensated. I see. I thought, thanks, Dad. From what I understand, you also treated the death of your parents in some way, comedically, therapeutically, humanly.

14:16I wonder if you could tell that story. I was shooting my travel show for HBO when 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 then 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

14:57and he said, you know, we're all thinking about you. It's in the news that your dad, you know, we've all heard the news and this is just how we all are with each other. He does the podcast with Jason and Sean, Jason Bateman. And whenever we're together, we always just joke about Bateman because that's just what you do. It's like the showbiz thing. And if I'm with Bateman, we joke about Will Arnett. But so I get this lovely thing from Will Arnett. He writes this lovely note. 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.

15:38It's just 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. My father had it right. Somewhere, a ghostly father was perched on my shoulder saying, yes, yes, this is it. See? Exactly. See, it is. So the story gets more remarkable because three days later, my mother passed in the same room that my father had passed in. They both had beds in the same room. and I've laid out now that I'm, I have space for comedy still. So Will texts me right away and says, and not right away, but he texted me after, you know, a little time had passed and he said, oh, you're, if you want, I could have Bateman take care of your sister.

16:32And I immediately texted back 3053 Beacon Street, apartment 17F, make it look like a robbery. And because I knew my sister, Kate, she would find it was funny. And so he read all that on the air and, you know, people were just like, oh my God. And it kind of went viral. And I, I, that is how I communicate. You know, that is, I'm a whale. He's a whale. We make these weird noises at each other. That's how we communicate. And I know that I, how much I love my parents. And I know what a lovely person Will Arnett is and, and Jason Bateman. And, but this, none of this is real, but it's this way of doing business and connecting.

17:31And when they all came out that I had thrown Kate under the bus and said, go get her, this is where she lives and make it look like a robbery. She texted me and said, you don't think I could take Bateman?

17:47I'm speaking with Conan O 'Brien and we'll continue in just a moment. This is the New Yorker Radio Hour.

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19:06This is the New Yorker Radio Hour. I'm David Remnick, and I've been speaking today with Conan O 'Brien. What mode do you want today, sir? Do you want grim, foreboding? Or do you want a more optimistic tone? Since leaving Late Night TV in 2021, O 'Brien has been busy. His hit podcast, Conan O 'Brien Needs a Friend, commands maybe even a bigger audience than he had on Late Night. He launched spinoffs to the podcast, and then the travel series, Conan O 'Brien Must Go, was on HBO Max. Last year, he was even in a movie. He played the therapist of Rose Byrne's tormented character in If I Had Legs, I Kick You.

19:47Let's return to my conversation now with Conan O 'Brien. How old were you when 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 um am i a math whiz no conan you are not um am i a tough guy oh god no conan you are not and it's lot of no's 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 an english I would write funny stories.

21:07The teacher would have me read them and everybody would be laughing because I'd put a lot of comedy in there. There's this one arrow in my quiver. There's not 35 arrows in my quiver. There's one. So I think I started, you know, probably working this comedy thing unconsciously in, you know, what, 1972, 1973? and Brookline Mass in a playground. And then you're just working it and working it and working it. And then I started seeing things on television or in the movie theater. 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.

21:58That's like the part of the map that disappears and there's dragons there. Like don't get into analyzing it. just what what's funny what's not funny which leads to really paying attention to the rhythm of warner brothers cartoons the classics the rhythm is perfection the comedy rhythm of those great roadrunner coyote cartoons a really good bugs bunny and the the timing and the expressions, it's all perfect. You're just soaking it in. You're not even aware of it. Let me ask you about late night. 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, certainly, 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.

22:55Yeah, 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'm i have a very uh ingrained wariness of sentimentality when i sort of google earth out of the whole thing and try to look at the whole picture i realized that there's things are constantly changing look at all the things that are changing all the time and so people are saying this is tragic you're like well i've said this to steven uh i'm i'm close to steven steven is steven colbert treating it as a tragedy or or what well i think steven very rightly is pissed he's yeah he's he's pissed i think rightly but he's also i think he's you He's got a big staff and he cares about those people.

24:00And I've been in that situation and that is excruciating. What I've tried to tell him is that there's so much of this really that doesn't have anything to do with you. I mean, I think it largely, you know, these giant glacial plates are moving and you are doing the best you can. And you've done, you're such a talented guy. He's done an amazing job. And yeah, there is definitely a thumb on the scale. We all saw that. And with Jimmy Kimmel, with the FCC, that was just outrageous and wrong. But in the larger picture, when you look worldwide and see voices being silenced, they really get silenced.

24:45I don't think that's going to happen with, you know, 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 and the travel show and getting to, I have all this freedom to be me in different ways, in different formats. 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 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 there are 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.

25:56So, um, and you can be master of your own destiny. You're not working for ultimately a giant toothpaste company or whoever it is 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 that when we were much younger, somebody died in an accident or a disease or something. You had something happened this year to two friends who had been guests at your house the night before, the Reiners.

26:39Can you talk a little bit about your experience of that horrific tragedy? Well, just it's to have, I mean, I knew Rob and Michelle and then increasingly got closer and closer to them. And we were, I was seeing them a lot. My wife and I were seeing them a lot 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. Um, you know, we talk about, I think I was in shock for quite a while afterwards. That was just, it was, I mean, there's no other word for it. It's just very, um, it's so awful it's just so awful and um i think about how rob felt about things that are happening in the country how involved he was uh how much he put himself out there um and to have that voice go quiet in an instant is still hard for me to comprehend.

27:52You know, I watched that Mel Brooks documentary that Judd Apatow did. It's terrific. And there's Carl Reiner and they have this, such a close relationship when they were, you know, both in their, I guess, 90 until Carl died. And then Rob Reiner pops up in this and he's, 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, I don't know, 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.

28:42I think it's seven movies that Rob Reiner made in quick succession that are classics. Now, to be thought of as a great director, I think 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, 10-year, 11-year period is insanity. You know, with Spinal Tap alone, if that'd been the only thing he ever did, he influenced my generation enormously. In comedy, Spinal Tap, when it came out, I was in college and it was like seeing, you know, splitting the atom moment. You have those moments where, you know, you see something truly remarkable.

29:30and another person i'd put in that category is we we just lost which is incomprehensible we just lost katherine o 'hara and that's someone who um was uh perfection you know and there is a tendency sometimes when people eulogize or remember we've all had that feeling where you're there someone's being eulogized and we're thinking to ourselves no they were they were good but this person's kind of laying it on thick um katherine is just i who's a funnier performer than than katherine o 'hara and what most and what people didn't get to experience personally was she is uh what she's was i'm still saying is She's possibly the nicest person I've ever met, just ever met, just glowed and goodwill.

30:26And but here I am on a podcast talking like this is, you know, unusual. This is this is what we're all contending with. We're always in the process. 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 um it's people saying did you hear uh and you walk around uh concussed for a week so that's what it is now i guess yeah i was in a good mood when i got on this podcast how you feeling now and you've taken me i just is the worst i mean you've this is a this is a colonoscopy right now and there's been no, there's been no profofol.