On with Kara Swisher - Conan O'Brien Talks to His Accountant

Episode Date: September 11, 2023

Late-night legend and podcasting impresario Conan O’Brien joins Kara to talk about the decline of late night, the writers’ strike, his $150 million deal with SiriusXM and his new HBO Max show, Conan O’Brien Must Go. They also trade notes on interviewing and … accounting. Questions or comments? Email us at [e-mail] or find us on social media. We’re on Instagram/Threads as @karaswisher and @nayeemaraza Photo credit: Gage Skidmore via Flickr Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Just kidding. This is On with Kara Swisher, and I'm Kara Swisher. And I'm Naeem Arraza. And our guest today is the comedian, host, self-deprecator extraordinaire, Conan O'Brien, who has that hit podcast, Conan O'Brien Needs a Friend. Are you going to be friendly today, Kara? Yeah, I think so. I think, you know, I've had this series of interviews with a lot of people like Conan, whether it's Jon Stewart or Jimmy Kimmel or Chelsea Handler, Samantha Bee, as well as Wanda Sykes and Lilly Singh on this show. I'm going to get to all of them at some point,

all these hosts. Are you taking over Late Night? No, Late Night is dying. So, you know, and as Conan said when he sold his company, I spent my whole life trying to get late night is dying. So, you know, and as Conan said, when he sold his company, I spent my whole life trying to get from TV to radio. So he's, you know, I think it's a really interesting time for people like him and he's been very inventive and entrepreneurial. So, you know, I just, it's a long line of these people I want to talk to about the changing economics and business. But Conan was hard to get. I mean, this is maybe why he doesn't have friends because we've been trading emails with him since last September. It's a year anniversary, maybe. I don't know if he's that hard to get. I think he was just busy. He's just been busy.

He's been traveling the world. He's been doing a lot of interesting things, including a show on HBO, I think it is. Yeah. And he's doing that these days in his new show. He's doing Conan O'Brien must go, going out. And he's kind of the diplomat America never asked for, but has gotten as he's trying to talk to people around the world. I would say that he's the favorite late night host of Gen X and elder millennials because he's been so omnipresent. This is according to unscientific surveys, obviously. He hosted the late night show on NBC from 1993 to 2009. It was on late enough that he got to be weirder and kookier than everyone else. Then he hosted The Tonight Show on NBC for seven months, had a tussle with

Jay Leno. And then he decamped to TBS where he hosted Conan from 2010 to 2021. Yeah, long time. He's been on, he's been part of the sort of late night for a long time. He's a surreal hard worker and someone who's tried really hard and others have, you know, in a way surpassed him in some ways, like Jon Stewart, I would say, and probably John Oliver and things like that. But he sort of pioneered a lot of this sort of ironic twist on the news and things like that. What I've always loved about him is how self-deprecating he is. His humor is so self-deprecating that he could be, I don't know, English or something. Yeah, it is. It's part of an act. I mean, it's all an act.

All these people have their things. But he's really, he's an interesting, you know, just different. He's just a different kind of comic. And I think he does a nice job on these shows. I have a lot of questions about where do you go if you have these particular and unusual talents which used to be at a premium and they aren't anymore. Yeah. He got out late night in 2021 and he probably wasn't a moment too soon. The ratings have been down for years and he sold

his company Team Coco to SiriusXM for $150 million. Allegedly. I don't know who knows how that happens. You'll find out. You'll find out how much he had and then make sure we get a piece, Kara. Yeah. He's a very talented guy though. He's really talented and I think he's always been super entrepreneurial. He always had really interesting comic bits and things like that. What's your favorite format or bit of Conan's? I like Triumph the Insult Dog. I always like Triumph the Insult Dog. I thought it was great. Because? It's funny. It's funny. It's really funny. My two favorites were his, I love the, in the year 2000 2000 y2k fear um and then also he used to do that mashup of like

beautiful people what their children would look like oh yeah yeah that was cute yeah that was always a hit yeah and so we'll ask him about all of that about his two travel series there's so much to talk to him about whether late night is dead the strikes why late night so white and his interview style yeah absolutely which is if your interview style is super direct his is much more winding but equally amazing yeah but he's very witty he's a really he's a very witty man and i'm excited to talk to him all right let's take a quick break and we'll hear from witty conan o'brien when we're back Fox Creative. This is advertiser content from Zelle.

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Hey, how you doing, Conan? How's it going? You know, I think it's good. You think it's good. All right. Well, let's- No, I don't. When I say that, I mean the planets are still in rotation kind of good. Oh, wow. That's a very hopeful view. That's a very low bar of good, you know? It is, I know. I know, because it could go off rotation,

then what will you do? It takes millennia, you know? So I won't be here when it happens. In any case, we met when I was working at the Washington Post. I was a news aide in the style section. It was a party for Tom Shales. But you remember Shales.

Yes. He wrote, if you recall, a devastating review of your show in 93. But in 96, he said you were the only good thing on Late Night. Yeah, that was quite a turnaround. I was eternally grateful for that. And that was very nice. That was something I did not see coming. But it was, you know, and it was a different era, too, in television where when you think about it, Tom Shales had so much power and it's hard to think of any. The media has changed so much that I'm hard-pressed to think of a television critic who could potentially end a television show. But Tom Shales certainly had that power. That's an interesting, that's a really fascinating kind of like a benchmark to look at the power

that, say, a Tom Shales had in the 1980s and 90s and today, where there's just a constant drumbeat of noise about television and people liking or not liking. And what does it seem to matter? I don't know. You sort of, I don't know how to phrase it, quasi-retired two years ago from late night? I would say I definitely, what I retired from, because what I retired from was the volume business of late night television. Because I loved it. I really did love it. And I did it for

28 years. And I did thousands and thousands and thousands of hours. And I'm told four of them are quite good. And I loved that very much. But what I started to see is that there were things that I became kind of more in love with. And the podcast is one of them, fortunately. That was just a happy accident. But another one was that doing these travel shows, going to Cuba, going to different countries and shooting remotes with people that I found and doing found comedy around the world gave me a lot of, I mean, it was electrifying. And I realized, you know, I'd rather be doing this. And late night had changed because there were so many late night shows. And I started to feel, okay, I've done this.

We only get so much time. And I'm no spring chicken. I'd like to really focus on some of these other things. So, you know, I— Well, the things you like, right? The things that you like, because it gets to be a grind. One person recently said one of the reasons that, you know, during the strike, and we'll get to it in a minute, there's not a differentiation between all you white guys, right? There is a differentiation of style. You have a certain

style. John Oliver has a certain style. John Stewart. Has that been a mistake to sort of have the same look for late night now that you're sort of reflecting it behind you? I think it's something that, you know, certainly over time, yeah, you can look at, I mean, I think a lot of pop culture in time when you look back on it can look silly. I mean, the 1950s can look really silly to us now. really silly to us now. And so can the 60s and the 70s, all for different reasons, but certainly having just a blank, you know, a mass of white males is not good and looks absurd now. And so, you know, at the time, back in the day, you know, I was, you have your blinders on and your nose to the grindstone and you're just doing your show and you're doing your best to make a late night show every night. And I'm very proud of the work that I did.

And then all this, you know, time goes by and you see the culture change radically. And the thing to do is just a combination of things. I think evolve, get out of the way when necessary, shut up when necessary, listen. All these things, I think, are crucial to evolving. And, you know, I'm trying to do that in my life, and I imagine a lot of my peers are trying to do the same thing. Or figure it out.

They're very confused, I know. I just was with Seth Meyers. I think they're all confused about what's happening. Well, Seth is confused in general. He was hit on the head about six years ago. It happened in a shopping mall. It's a tragic accident. He was reaching for a tall package and it hit him in a bad spot. So that's just Seth. And you weren't there to help him. I was there and I refused to help him. I just, no late night host helps another late night host. Yeah, it was weights and he really wanted to bulk up like Mark Zuckerberg.

Exactly. So, but interesting you use the term grind because what you've done is sort of become entrepreneurial. You have a podcast brand, you had Team Coco, just reported 180 million downloads a year. Your last series, Conan Without Borders, won an Emmy. You've got this new show coming out on Max, which we'll talk about. But about a year ago, you sold Team Coco to SiriusXM for $150 million. No, that was Canadian. What kind of deal is it? It's a five-year talent deal, but do you have any specifics?

I really don't. Oh, God, no. God, no. No one would ever hand me that kind of money. That would be a terrible mistake. I asked to be paid in real estate, but the problem is I wasn't specific. So it's all on the Florida panhandle and I'm told it's just, it's dreadful land. It's just really not, there's no aquifer, it's not, I never said I was a smart businessman, but, um, no, I, uh, yeah, I did sell, uh, and it's, it's been nice working with Sirius because they let me have, uh, a Sirius channel. So, um, that is a lot of fun because it's not just the podcast, but we can repurpose all kinds of stuff we did on late night that happens to work really well on the radio. And one of the things that just was a lucky accident is that I was never

aggressively topical in my comedy. We would do some topicality, but I think as late night hosts go, I was more absurdist and I just liked the silly and that stuff. It turns out there are pieces that I can watch that we did in 1997 or 19 or 2007 or, you know, 2017 that make people laugh now. They're just because they're working off universal themes. So it's really fun when I'm in a rental car to see if they've got serious and then put myself on. And it is the most solipsistic, ego-driven thing I can do. Yeah, and you just drive around.

As I just drive around, and sometimes if someone's with me, I go, isn't he something? Isn't he great? Do you ever do that, Cara? Do you ever listen to yourself and go, isn't he? Every day of the week and twice on Sunday. Isn't it fun to listen to yourself and turn to someone else in the car and go, I'm killing it. That was good. I'm killing it.

That was good. I did that to my wife the other day. But you timed it well before this industry-wide slump. Do you think they're getting their money's worth? What are they getting from you? I'd love to understand the terms of the deal. Anyone who works with Conan O'Brien is getting their money's worth. Trust me.

Okay. Because a lot of these deals. I'm a very hard worker. The podcast, which is a big draw. We get big stars, as do you. But yeah, they are definitely, no one's complaining. Let's put it that way. And if they are, I'm not listening. Right. But because some of those deals didn't work out. The Journal just published a report, which everyone knew at the time, was detailing how Spotify's billion-dollar podcast investment has flopped. Right.

Big-name podcasts like Harry and Meghan's and others, the Obamas. I always feel like, well, the good stuff does well. You don't have to sign. But when they were doing the celebrity deals, I was like, no, no, no. It's not going to math out, essentially, the math. Right, right. How did you think about it in terms of making money in the future of podcasting? Well, mostly thinking about it in terms of what's going to give us, and by say us,

this Team Coco company, what's going to give us some solidity, what's going to give us some security as we build out this business. So we have a nice space. We have a great staff. Eduardo's here. He's not paid. He's asked to be paid, but he's, I consider him volunteer, which I'm also told is illegal. But I, it's worked out. Talk about the economics. Are you involved in it? I'm quite deeply involved in the economics. I am not deeply involved in the economics. I have the same approach to my work as, say, the great slugger Reggie Jackson used to say, see ball, hit ball. And that is how I approach comedy, which is I will go in, I will meet every day with Adam Sachs, Jeff Ross, we'll talk about things, and then I will go in and I will do my best to make a lot of really good

content. And I will work with people who I think are good and talented and who also I think can provide good content. And I'll look at things where I think my talents could probably be put to some use and that might excite me at this later stage in my life, and I will do my best. And so that's the way I look at it, and I do not get into the weeds on, you know, 3%. Advertising, subscription, et cetera. No, I mean, what I get is I get broad updates, but they more or less deal with me the way— people speak to me the way they did to Reagan late in the second presidential term, you know? And I just sit there going, well, yes, yes.

Well, that's yes, yes. And I just know that I've—it's morning in America again, and I'm beloved. You're beloved. Is there a lifestyle difference in terms of being—because late-night television is a lot of jazz hands and a lot of it back in the day, I guess, back in the hot days. What is the difference in your life? I think I have less. I used to, for years and years and years, I would wake up every morning. And without trying to sound overly dramatic, but I am someone who takes, it's funny, it's not really funny, but I can probably come across to a lot of people as, oh, he's so silly, and he makes a lot of jokes, and he takes things very lightly. And I've never been that person. And I've never been that person.

I take things very seriously. And I am that person, but I also, when I'm given an assignment, I take it very seriously. And it's in my nature. I don't want to let people down. The good student. Yeah, exactly. So it's really the flaw of the quote good student is you're trying so hard to do a good job that you can lose sight of whatever art you're trying to make without sounding too highfalutin. So I think for years and years and years, I would wake up and I was so, so driven by what's the show today? How's it going? How did we do this week? What's the network think? How are things? Are we repeating ourselves too much? What's the next challenge? And I felt

that way for, God, I mean, I started in 93 and I I think that was my MO for 20-some-odd years. And I started to get better in the later part of the TBS show, but now that my life— What got better? I think it was eventually we went to—finally, towards the end, we went to half an hour. Eventually, we went to, finally, towards the end, we went to half an hour. And I remembered feeling a huge difference. Half an hour in an hour, it's more than just a 30-minute difference. I don't know how to explain it.

But you feel this responsibility the whole time for a longer period of time. So I don't know. I just felt that that helped was going to the—and, you know, you have to admit towards the end of my, or you have to remember towards the end of my run, COVID hit. And I think COVID accelerated things a bit because I was doing interviews, late night interviews on Zoom. And I remember just feeling, yeah, I don't, you know, I know this COVID is going to depart and things are going to go back to normal. But I do think to a degree COVID may have accelerated it a little bit. Everything. Meaning I would have maybe done, I might have done 30 years instead of 28.

But then I thought, why stick around for two years? As it's on its last legs. Yeah. As, you know, like leave now and it's still, I still, it's been fun. It's been such an amazing gift. I love this podcast. I love the travel shows. Let's do this transition now and let's not wait around to have some cool 3-0 anniversary.

You know, especially as you say, when there's this, the culture is changing so quickly. Yeah, the culture and TV viewership is down across the board. Ad revenue across the top late shows is down 60% from its peak in 2016, which is incredible. Obviously the recent strike didn't help. I agree with you on COVID. Do you know why it's down so much, Cara? It's because I left. You left. You know that, right? No, no, it's true. I've got a lot of data here that I will not share with you that says- I think it's maybe secular changes.

Yeah, it's been all into my departure. I'll look into that. So do you think it's on its last legs or not? Or do you ever think about going back to TV? I grew up watching Johnny Carson and there was was one late-night host, and then there were two, and then there were three. And I think at a certain point, the whole mechanism, I think the technology changed so that people have, you know, there were so many people that used to watch me because they didn't have much choice. Right. It's 1230 at night. They had to wake up and take a medication. Okay, I'm going to, or a baby's crying. I'll just watch

Conan because there wasn't a lot of choice. Now you have a choice, you know, between watching a late night host or anything that's ever been shot or recorded in the history of mankind. Do you know what I mean? You can watch Director's Cut of Lawrence of Arabia. You can watch any Merchant Ivory movie. You can watch all of Fawlty Towers. I mean, anything. So it's so much more difficult now.

Well, there was also, also you'd get FOMO as a viewer if you missed a big interview on late night. And it was sort of, there was nowhere else. And one of the things I'd love you to address is the changing sense of humor. You know, Late Night came under attack for things like punching down on Britney Spears, for example, mental state. That's just one example. Is it the changing nature of humor, do you think? I mean, obviously, you've been in comedy for your entire career. Is that something that's happened, or is everybody's a jokester? Now Elon Musk makes jokes. I'm not sure they're jokes.

I don't know what Elon's doing. But he needs to get better AI. He should fire his current AI and get better AI. Wow. Well, yes. I mean, obviously, if you look at old shows from the 70s, a talk show host could get a DUI and then joke about it on the air. And there's like applause. And, you know, that's just one small example. And there are thousands where people have become more sophisticated, more sensitive. And, you know, I have people come up to me on

the street and say, hey, Conan, isn't it tough today? You can't make a joke about anything. It's too PC. And I actually don't agree with them, I think. There's still plenty of things that are funny. And to me, that's kind of an excuse to say, yep, I'm shackled. I can't be funny anymore. Well, if being funny meant just being incredibly insensitive, that's probably not great. Yeah. You don't do political humor. Is that something that's eroded? You know, for me, it was always what serves the comedy and what's funny to me. The truest, most visceral comedy to me is always going to be Warner Brothers cartoons that were made in the 1940s and 50s. That's the stuff I grew up on that was shown in reruns.

So I liked that kind of comedy. I didn't, I was never as comfortable with comedy where I needed to make a point about something because to me that- Like Trump gave people the opportunity to do that. I just never wanted, it didn't serve comedy well. I actually think Trump has been, whatever people's, you know, people have say all kinds of, you know, he's committed all these different horrible acts.

But I think one of the worst is I think he's bad for comedy because it's so. Why is that? Because years and years and years ago in another lifetime when I worked on The Lampoon back in college, what we always knew is that you can do a parody of Sports Illustrated. You can do a parody. We would parody magazines. You can do a parody of Newsweek magazine. I wrote a parody of George Will where he's defending the feudal system. You know, it was like you can parody things that you can parody People magazine with its about its superficiality.

And it's, you know, put Brooke Shields on the cover holding a fish. Like, it's, you can parody those things. What you can never do is parody the National Enquirer because the National Enquirer cannot be parodied. The National, if you go and buy a real National Enquirer, it says Elvis cited in, you know, in UFO. He has tentacles for arms. Ghost baby turns into vampire and attacks Michael Jackson's ghost. You know, it's just like, it doesn't, there's no way to parody that. You can't parody something that already has that crazy irregular shape. It's not possible. So I always thought that when Trump came along, what a lot of people have to revert to is,

doesn't he suck? I hate that guy. He's an asshole. And those aren't jokes. And so I think it's just, you know, I'm really going on a limb here saying that's his greatest crime. No, it is.

I think he's hurt political comedy by being so outlandish himself. I think the January 6th thing is a blip compared to how much he's hurt comedy. Yeah, okay, good. I'm glad you went out there and said that. Yeah, it's about time. Everyone's thinking it. It's about time someone told the truth about Donald Trump.

We've talked a little bit about why late-night is problematic or is not doing as well, but I still like a lot of it, some of it. Make a case for it as an art form, or is it going towards someone like Greg Gutfeld, who's getting great ratings over at Fox at 10 p.m., doing mostly political humor on what is a micro-budget, it looks like, in a non-union shop. What does his success say about the state of lightning?

What do you like about it? Well, I'll first admit I haven't seen, and it's like anything else, like I drove a bus for 28 years and then I retired from the bus company. And so I'm guilty of, I don't ride the bus much anymore. I will walk rather than get on the bus. So I don't watch a lot of, I see little things here and there, but I don't really know Gutfeld. And that's not me just being knee-jerk, you know, Fox. And I'm not going to watch that, man. It's more like I honestly am not aware of what's happening. So I don't really know.

I just think that the bigger question isn't what's the future of late night because we all know that time itself is becoming irrelevant, meaning the time of night. Right, you can do it whenever you want. So I honestly, I think we're probably going to have to part company with the term late night at a certain point. And I'm not just saying this because I'm no longer part of it. I hate when people say, well, I've left football now and so now it's irrelevant. Well, no, that's a dick move. I don't believe that. I just believe that it was changing when I was there, and it's going to continue to change.

Go ahead. It's finished. Well, just that these talent, I mean, talent, I believe this. I believe talent will out. I believe that talented people who have something, a funny style or a way of connecting to people will continue to flourish. It's just that the medium will change around them. So it might not be called late night. For example, I have more young people come up to me. I took my daughter to a music festival to Outside Lens in San Francisco, and we had a blast. She's my liaison, my spirit guide to a much cooler, hipper world that I wouldn't normally see.

But I do love music. She took me to this thing. And so many young people came up to me. And what they all want to talk to me about is the podcast. And this isn't just propaganda. Me too. That's what they listen to. And they'll listen to that.

And it's in their ear. And they'll listen to, they listen to that and it's in their ear. And I've run into people who are, have their earbuds in and they'll tap me on the shoulder and say, I'm listening to you now. So. That happened to me the other day. Yeah. It's, and it's, I find that to be, that's erotic. No, it's really weird to.

I always, I always think of you as erotic. That's my first thought. You know what's sad? I say Conan O'Brien erotic. The fact that you're saying that right now means you consider it a joke. And I'm telling you, Eduardo, Eduardo finds me very erotic.

But I guess what I'm saying is what I'm doing, it's just still me. It was me in September of 1993. And it's me now. I think intimate is the word you're trying to get to. Well, yes, exactly. I have trouble with intimacy. Yes, I can see.

But I guess what I'm saying is instead of whatever the state of late night is, it feels like, well, no, it's going to be there will continue to be comedians and comedic people and they will exist in some form in whatever the technology is. So if five years from now podcasts are passe and there's a capsule that you can put between your cheek and gum and it slowly dissolves over the day, I'm going to try and figure out a way to get into that capsule. Yeah. Okay. All right. That sounds sexy. And mine will have a minty flavor. We'll be back in a minute. Thank you. find quality candidates fast. Listeners of this show can get a $75 sponsored job credit to get your jobs more visibility at indeed.com slash podcast. Just go to indeed.com slash podcast right now and say you heard about Indeed on this podcast. Indeed.com slash podcast.

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elevate their communication. Visit grammarly.com slash enterprise to learn more. Grammarly, enterprise ready AI. I'm going to switch to the writer's strike. It's affecting your new show, Conan and Brian Must Go, which we'll get to in just a second. It's affecting Late Night. I had Barry Diller on recently. He said that every month the strike goes on past Labor Day, essentially brings the whole industry closer. And he used the word collapse. How do you look at it?

Last strike was in 07, 08. Yeah, this is my third strike. My first one was 88, and I was a writer on Saturday Night Live. And I was a kid, and I remembered showing up at the picket line, and they handed me a sign, and the graphic was like an Underwood typewriter from 1915, 1920, and a big Ghostbusters thing over it. And so I'm walking in the picket line feeling really noble, and a middle-aged woman stopped me and said, so let me get this straight. You're striking because you want electric typewriters. I was like, oh, okay. That's embarrassing. Yes. We're tired of these manuals. We want electric. I went through that one, went through whatever, 2008. And so this is the third one. And I feel like for me to really understand this strike, I would have to be 25 years old and in a completely different position than I am now because I'm at the

later end of a very long career. And there's, you know, when I talk to younger writers, they tell me how difficult it is and how much the business has changed. And then I sympathize because I lived, I mean, I was, I don't know how else to say it. I was really lucky. I feel like a British rock star who came of age in 1964 with my band. And that was the time to be a British rock star. And we had a great run and we did stadium shows and it was really amazing. And it's much tougher for people making music today. I just think a lot of it, my time was so different. And I feel that I have tried very hard to understand, you know, I think the Netflix of it all and the streaming is so complicated and it's so,

you know, they don't reveal how a show is doing. And that was such an essential part of my life as a TV performer is you knew every second how you were doing. Yep. It was transparent. It was transparent. And now there's a black box. I don't understand that. And, you know, it's also some of these companies are so big, you know, Apple, Amazon, that this isn't even their core business. They would, this is like a lemonade stand they've got going.

Yeah, I always tell creators, they're selling toilet paper at Amazon, just so you know, that's what they're doing. But in the last strike in 07-08, you paid your staff before going back on air. staff before going back on air. Talk about that because other hosts now who are doing Colbert, Kimmel, Fallon, Myers, and Oliver, a very diverse group of people, have recently gotten together to make Strike Force 5, a podcast to benefit their staff. Talk about this in supporting them because these are all union shops, as I said, the ones on Fox are not. How do you think that works out? That's not really a solution to the problem. No. And why didn't they invite you, by the way?

Well, I think I'm the old man, you know? Yeah. I think there are these punk kids running down the street, and I'm the old man looking out the window eating tuna out of a can. Why are they doing this without me? No, I just mess it up. Um, I, they were, they did the right thing. I, I think the, uh, I think everyone has their own attitude about it. Mine was, um, I started out as a TV writer. I'm very connected to my writers and would hang out with them sometimes too much. I would get kicked out of the writing room because I would be doing so many bits that I was wasting time. And they would laugh and then they would say,

you know, you really got to go because we have to write tomorrow's show and you just keep doing these bits that are taking it in the wrong direction. And so for me, I always felt very close to my writing staff and I felt like we're in this together. And so it felt natural to want to try and support them, help them. And I think a lot of people would feel that way. You know, if you're working, it's not the same as, I was not the corporate vice chair of Exxon, and I was saying, oh, there's a trouble on Platform 17 off the coast of Buenos Aires. I'm going to go over there and hang out with those guys, men and women, and chip in. I never ran a giant shop. I always felt like I ran kind of a mom-and- pop cookie factory in a Keebler's Elf tree.

And so that creates a very different dynamic. Between you and the- Between me and the people I'm working with. And I think we followed that through on the podcast. It's very, Eduardo, you feel free to jump in. I agree. But it is at the risk of being fired. I disagree. Yeah. He's blinking in Morse code. Please help me. This is my location. But no, but it's,

so I think it's just keeping it really simple, which is, I think when things get big is when things get very complicated. So obviously when these companies become massive and the profits are massive, that's when people lose touch. And when I say people, I mean I always like to remind everyone that the evil person that you're against is just another version of you. We're all humans and we are all – when you get up in front and close to people, you often quickly find out how much alike we all are. So it's just that the structures have gotten so big. They're so massive that, you know, there can be so much misunderstanding. There can be... Yeah, there's been a lot of it here, for sure. And that's what slowed it down.

Yeah, and I do think, unfortunately, you know, it's a deal. A good deal is where both sides are somewhat disappointed. Right. What's the effect on your new show, Conan O'Brien Must Go?, which is a travelogue. Yeah, it's a travelogue. With costumes, yeah. Yeah, a costume drama. With costumes, yeah. A costume drama.

It is basically a version of what I was doing, but with a twist, which is I talk to celebrities on the podcast, but I also talk to civilians around the world and have conversations with them. And then I show up unannounced in their country and get involved in their lives. Give an example. So it's the concept of you just show up and make yourself irritating. Yeah. Talking to some, a guy who runs a fishing boat and off the coast of Bergen, Norway, and he really, oh, actually he's up at the Lufthansa Islands. I'm sorry. He's up, which is even further North. And he has a fishing boat and he doesn't really get along with the guy he's on the boat with. And we chatted for a while and I decided I'll go up there and counsel these two on the boat. And it was really fun. And it turns out I'm terrible fisherman. But it was,

it's also just an excuse to get into the country and do the kind of travel comedy that I've always loved doing. How did you sell it? It sounds like a fantastic boondoggle for you. Does it make money? How did you convince them? Well, we haven't done it yet. So we did two of them. It could be a complete sinkhole of money. No, the trick is to keep the cost down. So I make all the clothing myself. I like your Viking outfit. Thank you. That looks nice. You look good as a Viking. Thank you very much. It's the DNA.

It's in the DNA. I'm a redhead. So you're trying to save money. Like how? Oh, no, no, no, no. Not save. No, I'm just saying we're able to do it on a, we have a decent budget

and I think we are making good content and we made- What is the budget? What is the budget purpose? I don't know the budget of this show. I don't remember. Good Lord. I've got to get Jeff Ross on the line. I need the budget? What is the budget purpose? I don't know the budget of this show. I don't remember. Good Lord. I've got to get Jeff Ross on the line.

I need the budget. I feel like I'm being audited, Cara. What's going on here? What is the budget? Now, wait a minute. Who got coffee? Did you pay for the coffee yourself? Where's the receipt?

I don't know the budget of the show offhand. All right. What I'm wondering is what's the economics of it? What do you consider success on this show? How do you, you know, you're going to give streaming numbers? Are they telling you? Oh, I'm going to completely black box this thing. No. Conan's doing quite well. There's no reason to even question it. Trust us. No, we're going to, it hasn't even come out yet. So I will be made very aware how it does when it does come out.

We only made, we made two episodes, two, they're specials, essentially. We made two specials that were never, and we wanted to make four and release them all at the same time, but only two are in the can. The writer's strike came along, so we shut it down down and it will remain shut down until things get resolved. So it will be showing up God knows when now. I don't know. But when it does, it's going to make billions of dollars. Billions. Why not? So once this travel thing is over, what's the next thing you're going to work on? I don't know. Probably dying, passing away. I don't know. I have no idea.

I'm working on my death after that. Yeah, I really want to give it some thought. Given your advanced age, how do you look at, like, the AI issue in this strike? It's a bigger one beyond the strike. Is that something that worries you? You know what I have to say? Well, you know, it's funny because I read a really good piece by Simon Rich, great comedy writer. And he wrote a piece where he got a really good look at AI, not chat, GBT or whatever, but he got a look at the AI beyond that.

And it frightened him because it was so good. And it wasn't so much a comedy piece. He was just talking about his natural reaction. good. And it wasn't so much a comedy piece. He was just talking about his natural reaction. And then he said at the very end, the thing that I thought was very powerful is he said, look, whatever this thing is, I know me. I'm still going to write. I'm still going to obsess over thinking of weird ideas. I don't know what I'm going to get paid, but there's a compulsion to do this. And I think, I know this sounds very optimistic because I, it's so big. It's so much bigger than all of people, whether they're comedy writers or TV writers, movie writers, people that write novels, essayists. There's just going to be whatever the

computer does, there's going to be something, I believe, and this is just me, that drives us to keep going in different directions that simulated intelligence can't come up with. Meaning computers can't be funny? Well, just like, you know, I mean, the analogy I've heard other people use, this is not mine, but portrait painters were around for thousands of years, and then camera shows up in the 1840s, 50s, and 60s, and suddenly painting becomes different. You know, you get cubism and blue periods and abstraction. And so it's possible that—I do think that the Guild is absolutely right to investigate and to do as much as they can to protect writers now from AI. And I think they're- And actors. Exactly. And actors and people protecting their images. I think they are 100% right to do that

and to do everything they can. And then beyond that, I just have to have faith that it's humanity's job to evolve past what these machines can do. That's the second corollary to this. That might be overly optimistic. I've been accused of that before, but. I feel like it is. You know, it's interesting when you think like, remember Mac's headroom and stuff like that.

You just dismissed everything I said so quickly. I think it can do a lot. Look at everything that's replaced already. But listen, okay, but guess what? If they can do a lot, I don't think we can legislate our way out of it. You know? No, we can't.

I mean, that's the other thing too, is that if there, so my vision is the one that offers some hope. In your vision, these things are our overlords five years from now. And I don't care what deal gets worked out. Oh, nine, let's make it nine. No, I do.

Here's what I say. I'm not afraid of AI. I'm afraid of the people who own the AI. That's who I'm afraid of. And it's all the big companies. Speaking of big, they're even bigger than that. And they'll impose it because they impose it on communications. Right, right. I want to wrap up some questions about interviewing. That's what you do on the podcast and what you did on Late Night for almost 28 years. When do you think about interviewing the platonic interviewer and what's their role? How do you approach it?

You know, people go in with different agendas when they interview. I have always tried to figure out, especially back when I was in the volume business game, where you're talking to three people a night, five nights a week, you know, and very few vacations. You're talking to a lot of people and people are coming through that you might not naturally be interested in. I would always try to find out, I am a curious person and I would try to find out what am I really curious about with this person? Because that's what drives a conversation is what are you curious about? As I moved on into the podcast, I talked to fewer people. And there were almost universally people that I really want to talk to.

I'm very fortunate that way. But I still, I'm always fascinated by all these skills people have that I don't have and all these things people can do that I can't do. And I want to know about that. And so that just drives the conversation. The curiosity that you describe your interview style. I'm very curious, but I also, I think I have a need. It was probably a disadvantage in parts of my life, but I really do like to connect with people. I really want to make that connection and that drive to make that connection. And I do this, you know, I will chat with people on the street or in a restaurant for a very long time. And I will ask them about themselves to a point

where it's sometimes ridiculous. And they say, look, Conan, I just wanted a selfie. I gotta go. You know, and I'm like, okay, right, right. But that is part of me. I do like to connect with people. That's a high, I get a contact high off of that. So that's your specific goal. What do you want the audience to get out of it? You know, I used to, I've always thought that there's a responsibility as a host to be a host. And that part of that means it's a luxury to put somebody down. It's a luxury to mistreat them. It's a luxury to be rude to them. And you shouldn't have that luxury unless it's really merited. If someone is being an asshole, if somebody is disrespecting you, then the gloves can come off.

But other than that, it's your job to take care of them even when you're not having a good time and you find them to be really distant. I, as a host, and that's kind of an old-fashioned, you know, Catholic upbringing. I just thought, I'm the host of this fucking thing. Of all the interviews you've done, who was the worst guest? Oh, well, I hate to put it all on them because it just feels... It was your fault.

You think it's your fault. Sure. I think really early on, really early on, and it wasn't like, I just didn't have the chops yet. It was like 1993, I think, and we had Eartha Kitt on the show. And I just, she was very much, I'd say like, no, you worked with James Dean. And she'd say, well, what do you care about that? She was very challenging and provocative. And I think if I had had more seasoning, which I got quickly, but I didn't have it then, I would have been able to turn that on its head

and had fun with it, but I wasn't able to. And it was just, you know, not good for her, not good for me. Just, and I remember after that interview thinking, I just, that was bad. That was really bad. And I was very, you know, at first knee jerk. Why was she so difficult? And then realizing,

no, it's an opportunity. It was an opportunity, and I just wasn't there yet. It was, I had just got out on the court and tried to make a three-point shot, and it went into the audience and killed a little boy. So that was, that was, and- Well, it's Eartha Kitt. I would tread carefully around Eartha Kitt, but I'd slap back, yeah. Yeah, I mean, she famously, that was, um, and, and. Well, it's Eartha Kitt. I would, I would tread carefully around Eartha Kitt, but I'd slap back. Yeah. Yeah. I mean, she famously, uh, you know, went after LBJ at the White House in like the late sixties. So she was not afraid of anything.

And I just remembered, uh, it was the kind of interview where I'd say, would you have for breakfast today? Um, what do you care? You know, it was that kind of thing. So, uh, it was just going nowhere fast. you care? You know, it was that kind of thing. So it was just going nowhere fast. And that famously was one where I thought maybe it would be best if I was just hit by a car and someone else hosted this show. I don't know that. Yeah, right. Who made you most nervous in the lead up to an interview? That's really interesting. I would say, you know, it's funny because the nerves went away at a certain point.

I would say initially, the first time I interviewed Paul McCartney, just because I'm such a music person and I know when you idolize someone and you know too much about them, it actually hurts the interview a little bit. And so I know, I mean, I know what he had, you know, for lunch on February 3rd, 1967. So I probably shouldn't even be talking to him. So I got over it because we, you know, we ended up talking a bunch of times over the years. Because we ended up talking a bunch of times over the years. But the first time I remembered he's talking and I was looking at his hands as he was talking and thinking, so those are the hands that made the shape of the F chord when he recorded. You know, you're like, what are you doing?

It's just, it's. You're too much of a fanboy. And it's, yeah, and it's, it's also, you're fetishizing this person and it, it gets into religious relics. Like those hands should be put in a pot and people, old women should have to bow before them and say their rosary. You know, it's just stupid. So I have two more questions. Interview you're most proud of? Hmm.

Wow. Wow. I'll answer mine. Steve Jobs and Bill Gates together. I'm going to say the same thing. By the time I interviewed Steve Jobs and Bill Gates together, it was right after you. You had just left the room. And they both said, man, that was a drag. And I said, cheer up, guys.

Cara's gone, and now it's fun time. Because they're super fun. Bill Gates is hysterical. I don't know who was the most, say it again, it was the most excited? Proudest of. Oh, proudest of, yeah. Proud. Wow, I don't know.

I have to say, I mean, it might be kind of unusual. There was one, I got to talk to Robert Caro, and I just thought, sometimes when you get to stretch a different muscle, I'm not going to say that that's the answer. Because I obviously, it's been too many people and too long, and I can't say. But sometimes it's the person you're not thinking about. It's the historian. It's the biographer. It's the, you know, people might think, well, it must have been so exciting when you talk to, you know, whatever, a famous rock star or a super famous, you know, movie star. Yeah, no. Johnson and has spent all of their life quietly working away on an electric typewriter in a small office in Manhattan to build something. And I felt like I had a good connection with him.

And I was very proud of that because I was a fan, but I also felt like, okay, I think I did well by him, which made me feel good. That's a good choice. That's a good choice. Last question, who's the dream guest you have not been able to book on TV or your podcast? Who would you be like, that is who I want to talk to? Oh, man. Well, you know, the funny thing is, the caveat to that is, do they have to be alive? Because for a long time I thought... Oh, okay. Give me a dead person. Well, I used to think when I first got my show, Nixon was still alive. And I used to think, to think when I first got my show, Nixon was still alive. And I used to think, what an amazing interview because he is, when you think about it, he was like the comedy figure of the second half of the 20th century. I mean, people were, you know, immediately recognizable.

Everyone, all comedy revolved around Richard Nixon. And, but he was also clearly had probably knew a lot of things and had a lot to say. And if you could get him past these insecurities and foibles, he might have some really cool observations. And I just thought, what an amazing, like, what if it got silly with Nixon? Wouldn't that be absolutely fantastic? And I'm not even saying this. This has nothing to do with, hey, I just listened to Conan with Kara Swisher, and apparently he's a big Nixon fan. No, it's not about that. It's about I remember thinking he would be the ultimate guest because it would be a great historical guest and also a great comedy guest because what if I could get him giggling or what if he

could, you know, what if it just got outlandish in some way? All right. Did you have a dream guest otherwise that you would love to get that you're not been able to? Wow. I don't know. I just, I feel like, uh, who have I, I don't know who's, cause every time I say them, there were, you know, they, they come along and then I go, oh, I mean, so I don't know who's left. I hate that question. I hate that question. I want to interview Dolly Parton and Taylor Swift together and not talk about boyfriends or Kentucky.

Only about business, about their tough business lady. Right. Are you going to ask them, like you did me, what's the budget? How much did you clear? They know the budget, Conan. I don't need to ask them. They know the budget. I'm not sure they do. I mean, Dolly will know the budget. Taylor won't know it down to the number. Taylor will know the budget. She might. She might. You went from she will to she might. No, she's very good. No, she will. But you can be a good business person and not know every single detail of where the money's going. Okay, all right, all right.

Now get over it. That's called trust. It's called trust, Cara. Eduardo, you're not stealing from me, are you? No. Thank you so much for coming on the show. All right, so nice talking to you. I appreciate it.

And Eduardo? Yes. Eduardo? Yes. Keep stealing the money. Is that what you think, Cara? You think everyone's stealing from you? No, I just was funny. He doesn't, I'm not surprised he doesn't know a lot about his business, but that's, you know, no. Do you think he actually knows more than he lets on? No, I don't. I kind of, you know,

I appreciate his approach. I loved his, where's the ball and he hits it with the bat kind of. I think you can't do that in this day and age. I think you have to be really intimately involved with the finances and everything else of what you're doing. That's just me. But I can see he's come from a world where, you know, every time he says, I'd like some Diet Coke, it shows up for him. I mean, he has good partners, right? His producer just got the top job of programming at SiriusXM. And so he has partners that he trusts and I guess like lets them take care of the bits that he doesn't want to do. Yeah. I actually, I just really liked him as a person. Did you? Yeah, he's lovely. He's always been lovely. I mean, you can tell how thoughtful and

smart he is by his comedy. I think it's never been mean. It's super thoughtful. Like he says, it has an evergreen quality to it. Yeah. I agree. I think he's just, he's been consistently funny in a situation where he has a lot to produce over the many years. I appreciate how he kind of spoke about what drives him and his curiosity and his desire to connect with people. And I think you see that in his show. He is so humble. I died when he said that he was Reagan in the second act. Yeah, that was cute. Yeah, he's really cute. That was cute. Yeah, he's really cute. He's funny. I do think, though, someone like John Oliver is so much

more relevant to young people, though. I mean, just knowing young people, like, they like... It's changed a lot, and you have to really have a point of view, and he was more of the old school, which I think is... He was better at it than, say, a Jay Leno, but it's still... You know, he's got a... I like that he's reached out on his own, and he's a very good

podcaster, and I think people really enjoy it. I think what he's doing with these global shows, The Diplomat America Didn't Need is interesting. I think he is obviously very thoughtful, intellectual. He doesn't do, I love John Oliver stuff, obviously, but he's not trying to be in the newscaster business. He's trying to be in the observation business. And I also like, he was so kind and so humble. And like, so I love that he believes in luck because a friend of mine, Pan Pan Wong always says, if you don't believe in luck, you don't have compassion.

And I love that. I think that he has a lot of, it kind of makes sense. He works hard. I think he works hard. He's a very thoughtful person. He's a real, I really enjoy talking to smart, thoughtful people and they're all different, all these hosts.

And he actually was one to pull out of political comedy, I think like two months before his show ended, he said, I'm not doing any more Trump jokes, right? And his little bit on Trump was hilarious. But did you buy that, that he's unparodiable, that he's done something? He's got a point. It's at some point you just sort of yell. I mean, that's what Stephen Colbert is doing. He yells at Trump and that's satisfying to the people who don't like Trump. And so he does box you in a corner. And ultimately, yeah, I think he's so ridiculous and also dangerous. It's very hard to, it's hard to be funny because it's not funny.

And at the same time, he's ridiculous. And so I think, yeah, I think that's right. Although he, like Trump, was into hands. He was noticing Paul McCartney's hands. Just like we discussed Elon's hands the He was noticing Paul McCartney's hands. Just like we discussed Elon's hands the other day. Hands are having a moment. Have you ever been so impressed by somebody's hands on a podcast during an interview?

No, I never noticed their hands. I never do. Not once. Well, I appreciate that Robert Caro is his favorite. He's a huge fan. He underplayed it, but he's quite a big fan of Robert Caro's and has talked about it extensively. Yeah, I think Robert Caro is also one of those people he's like, I saw him at the PEN America Gala recently and I had complete jitters. I don't really get nervous around celebrities, but he is so... Yeah, he's definitely, you know, the people who love him really love him.

He's got a real fan base among those who want to read extensively about LBJ. Does that mean you don't want to read extensively? Not particularly, but I get it. I get it. I get it. For those who want to, we're going to go, we're going to let them read about LBJ and you're going to read us out, Cara. Absolutely. Today's show was produced by Naeem Araza, Christian Castro-Rossell, Megan Cunane, and Megan Burney. Special thanks to Mary Mathis. Our engineers are Fernando Arruda and Rick Kwan. Our theme music is by Trackademics. If you're already following the show, you get to host your own late night show.

If not, you get to host your own late night show. It's the end of an era. Go wherever you listen to podcasts, search for On with Kara Swisher and hit follow. Thanks for listening to On with Kara Swisher from New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Thursday with more. Autograph Collection Hotels offer over 300 independent hotels around the world, each exactly like nothing else. Hand-selected for their inherent craft, each hotel tells its own unique story through distinctive design and immersive experiences, from medieval falconry to volcanic wine tasting. Autograph Collection is part of the Marriott Bonvoy portfolio of over 30 hotel brands around

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