Conan O'Brien Is Adweek's 2022 Media Visionary

Conan O’Brien considers himself a lucky guy. And not only because he was fortunate enough to spend 28 years reinventing late-night, first when he was NBC’s surprise pick to replace David Letterman as Late Night host in 1993, then followed by an innovative 11-year run on TBS’ Conan, which ended in June 2021. O’Brien is also keenly aware that luck has had an outsized role in the unbelievable breaks that came his way, starting with the way the Late Night job somehow fell to someone who, at the time, had just logged a few years writing for Saturday Night Live and The Simpsons. “So anyone in this business—and I'm gonna go further than that, I think anybody in any business or any endeavor—who doesn't carve out a healthy chunk and assign it to luck is deluded,” said O’Brien. However, becoming a TV icon isn’t just about luck, but also having the talent, intuition and tenacity to capitalize on those once-in-a-lifetime opportunities. For O’Brien, that meant staying focused and finding his sea legs during those early years when NBC repeatedly tried—and failed—to find his Late Night replacement after a rocky start. He also leveraged the unexpected social media-fueled frenzy that erupted around his infamous 2010 exit from The Tonight Show—after the network attempted to return previous host Jay Leno to the 11:30 p.m. time slot—into a sold-out U.S. concert tour, followed by a new late-night home at TBS. Then, most recently, he turned a throwaway side gig—his podcast Conan O’Brien Needs a Friend—into a full-fledged podcasting and audio empire via his Team Coco media company, which SiriusXM purchased last May for an estimated $150 million (see sidebar). The deal not only keeps O’Brien’s podcast going for another five years, but also includes the creation of his own Team Coco comedy channel on the satellite radio platform, debuting later this year. What’s next for O’Brien, Adweek’s 2022 Media Visionary, after conquering late-night, broadcast, cable and podcasting? You guessed it: streaming. He’s finally focusing on his next TV show for HBO Max, which he’ll turn his attention to this fall. But before that, in his first extended interview since leaving TBS more than a year ago, O’Brien reflected on his extraordinary journey as well as his current time away from late-night and how his podcast “saved” him. This interview has been edited for length and clarity. Adweek: This is now the longest you’ve gone in three decades without regularly being in front of an audience. What has that been like for you?Conan O’Brien: That’s the part I miss the most. I love being in front of people. I still grab opportunities to do it. The author-illustrator Randall Munroe writes these books called What If? that are wildly popular, these science books that are quite funny. My son's a big fan. And his people reached out and [asked], would I be willing to host a book event here in Los Angeles for him? And before they could finish the sentence, I said, “Yes, I will do it. As long as there's a crowd I'll go there. I don't need money. I don't need a free book. I don't need anything.” [laughs] That’s the part that I miss, and that I am looking forward to being back to. I was rewatching the Conan O’Brien Can’t Stop documentary about your 2010 tour, and a big part of that film was the urgent need of yours to be in front of a crowd. But even though you do miss that, it seems like 12 years later, it’s not as urgent as it was back then.I think you're right. I think that there were many years where that was all I knew: You get up and you do this every day. I think we computed over 4,000 hours of television [that I’ve done]. You get to the point where it's part of your metabolism. There's some part of your lizard brain that knows every day, I need to secrete this fight or flight hormone to get this idiot out there and take away all of his inhibitions. So what happens is, if you break the cycle for a while, things do start to calm down a little bit. And what I love is the podcast, in so many ways, has saved me because we started it before the show ended. How so?[It’s] a completely different way of relating. I don't get instant feedback, but I also don't rely on some of the cues that a live audience gives you, which can sometimes lead you too often to go for the joke as opposed to really dig in and explore. You think about the old format [on my TV show], it was five-minute interview, get out on a laugh, commercial break, then four- to five-minute interview if you're doing two segments, and then get out on a laugh. You get that ingrained in you, and I'm not saying it's bad, but like all things, it has its pluses and minuses. And this new format, after so many years of doing it one way, has been very freeing and feels like I'm using different muscles. Let's pretend I had muscles, I would now be using different muscles. What do you wish you’d known before you started Late Night that would have helped you get through those tough early years?I wish I had known about antidepressants. Because I didn't. All the feedback I was getting was from the network and television critics [and] was resoundingly negative. What I didn't know for a while is that there were all these 15-year-olds, 16-year-olds that were watching that never had a problem with it. They immediately said, “Oh God, this is so weird and different. This is for me.” But they had no way of communicating with us (this was pre-internet). I wish I’d had some way to know that. When did you start to feel you were finally getting things under control? After the first year. The saving grace was the studio audiences. Because you're getting what's supposed to be very official feedback. These readings, these metrics that tell you: network: unhappy; critics: unhappy; ratings: not where they should be; affiliates: not happy. What no one was taking into account was that [at Late Night’s] Studio 6A, if we did five shows a week, I would say four times out of five the audience seemed really happy with what we were doing. And you were getting laughs and we started to build more and more bits that, when we announced them—the Clutch Cargo, In the Year 2000, Staring Contest—there's a cheer. That was giving me a signal that was more profound than all the negativity. I'm naturally a humble person. But you don't go through a couple of years like that and work that hard and not come out of it with some humility and some sense of [having gotten] lucky. I remind people that all the time. We worked very hard, but I could easily have gone away in ’94 and been, as someone once said, a Trivial Pursuit question. I did everything in my power to make sure that we would survive, but we needed luck, too. And that, I didn't supply. I don't know where that came from; we just got lucky. I know NBC was trying to replace me, but it never quite lined up. And then by the time they got around to it, someone said, “You know, it's actually doing pretty well.” We worked very hard, but I could easily have gone away in ’94 and been, as someone once said, a Trivial Pursuit question. I did everything in my power to make sure that we would survive, but we needed luck, too. Skipping ahead to your next trial by fire moment, your Tonight Show exit, does it feel strange to explain to people now the importance of that franchise to you at the time, given how much has changed in late-night since then?At this point, even beginning to try and explain to people all the different ways in which I thought that was a screwed-up situation—and in some ways unjust—is absolutely asinine and feels completely stupid and self-indulgent. But it was really important to me. I will admit to you, I am not a seer. I'm not a tech visionary. I'm not a revolutionary thinker. Talk about luck: I happen to exist at a time when the internet at that point, 2010, is really starting to flex its muscles. There was this explosion online, and that took me completely by surprise. I didn't see it coming. I remember at the time, there were people at NBC that—I always picture them in their black tower, going: [shocked indignation] "How is he doing this? Release another falcon. Stop him!" But no, I didn't [organize] that. That was a lot of young people who thought it was bullshit. And they use the internet, so they went to town, which led to this grassroots movement. From there it was immediately this feeling of: “Let's do a show for these people.” O’Brien and sidekick Andy Richter's staring contests were a popular Late Night segment. Which led to your tour after you left the Tonight Show.It’s an interesting example of, take what you've been given. My sense of humor didn't change, I didn't change as a person. But the situation changed completely overnight from, I'm heading the oldest late-night franchise in America, the storied Tonight Show, to that's over. It's about adaptation. I really didn't want any of that craziness with NBC or Leno; I wasn't looking for any of that. But once it happened, and this is the situation, you react to that situation using what skills you have. And then you proceed in the new: What's the new reality? The new reality is, now I'm doing this in theaters. Hey, there's a big upside to this. There's an incredible energy in here. And these theater shows allow for so much more vaudeville, for lack of a better term, than you can do on a Tonight Show or any show like that. And then that led to, well, who would we do the next show for? So how did you end up at TBS?A lot of people thought, "Well, he'll go to Fox." But they said, “They don't have affiliates lined up [at 11 p.m., when the show would have aired]. So you gotta go on the road and convince affiliates [to free up their 11 p.m. time slots].” And I thought, "You know what? No. I want to go someplace where maybe we have a smaller audience. Maybe it doesn't have the reach, but I want to work with good people who let us do our thing, and we're somewhat protected." [Former Turner Entertainment Networks chief] Steve Koonin came along, and his pitch was so much less slick than everybody else's pitch. But I could tell, this is a really good man and he has the same idea I do. That was one of the best meetings I've had in my life. We were on TBS for 11 years, and we were completely supported, 1,000%. When people stop me on the street, it's [for] the work I did there. I did a ton of remotes, travel shows, Ice Cube and Kevin Hart in a car. There are all these moments that we had that bounced around YouTube and Facebook. It's a good body of work. And that, again, was looking at the situation as it was and making the best decision, given the new reality. I had to let go of that idea that my destiny was the Tonight Show, which even as I say it now, is ridiculous. For a million different reasons, it didn't work out. So move on, and don't waste time moaning about it. You have the skills and these abilities, and there is a thing here that you love to do. Do that with the tools you have at hand. That same kind of thinking leads to the podcast, which leads to other things revolving around the podcast. What was your response when you were pitched to do a podcast?I was in our offices at Warner Bros. talking about different things we could try. Something I’ve learned is, always have people around that are smarter than me in ways that are different from how I'm smart. Someone said, "You should do a podcast." And I was sarcastic, like, "Oh, really? Because I’ve been on television for, at that point, 25 years. So a podcast is what I should do, you think? That's good thinking.” I was pretty dismissive. Then I said, "I could interview some staff members and see how it goes." And then my producer, Jeff Ross, said, “Well, there might be a dealbreaker here. For it to work, you'd have to read ads.” And I said, “Do I get to read them as myself, in my own personality?” And he said, “Yeah.” And I said, “I think I'd love reading ads.” Which is not a phrase you never hear celebrities say.For me, I was going back to … I'm such a geek for old media. I used to love listening [to and] watching people who were funny, seeing old clips. This was back before the internet, you'd have to go to the Museum of Television and Radio in New York, and I'd go there and just look at stuff. And it was fun to see Steve Allen interrupt the comedy for a second to do an ad. Because he was still Steve Allen, and sometimes he was being funny about it, and you could tell he didn't really give a shit or he's doing it in his way. There are ways to talk about a product, and everybody knows, “Oh, that's Conan. He's doing this thing he has to do because he's got to make things pay for themselves, the way we do!” What else have you loved about podcasting?The biggest joy of doing the podcast is that it's essentially what I've been doing my entire career. But it has a completely different focal length. That's one of the discoveries of this world, is that there are so many different ways now to be funny, and one shouldn't be afraid of them. One should give them a shot and not be afraid of risk. I think if my podcasts had been a failure and lasted just a couple of months, you probably wouldn't even be asking me about it because the penalty for trying and losing is not that bad. So that's been a delightful discovery for me. As I get long in the tooth, they keep coming up with new ways to humiliate oneself. That's one of the discoveries of this world, is that there are so many different ways now to be funny, and one shouldn't be afraid of them. One should give them a shot and not be afraid of risk. You’ve talked many times on the podcast about how invigorated you’ve felt by doing it. Did it accelerate your decision to step down from the TBS show last year?I honestly think two things accelerated it: having the podcast, meaning, if I had no other outlet to be me and there was no way to reach people, I could see being more reluctant to step away. So, yes, the podcast helped give me many ideas for other things I could be doing with my time that still allowed me to rant like a madman. And I think Covid accelerated it a little bit. Doing interviews on Zoom, being away from the studio, maybe laid bare for me how, OK, I've done this for a long time. I'm really proud of what I've done. I don't know that I have anything else to add to this nightly televised thing that shows up at 11 o'clock. I thought, "OK, this is a good time, nothing lasts forever. Let's do this now, and then there's a chance to reinvent and reapproach rather than [I] must keep cranking these out." His TBS Conan Without Borders travel shows included an Israel trip. Why did you decide to expand your podcast into an empire?That was my team. I can't take a lot of credit really for the larger business other than I was there to say, “Yeah, that sounds fun, and I will happily go on [other podcasts within the network] to try and help push it when it first gets started.” It became a fun project for all of us to get together and try and make this thing happen. There was no mandate at the beginning. Once you start moving and one step leads to another step, very quickly this flow takes over and things happen. We’re making things that I would want to listen to, and that gives me a lot of joy. One of my favorite people of all time is Dana Carvey. He and his sons have been working on a project for us called The Weird Place. And what's more fun than working with Dana Carvey on a show where he's letting his imagination go completely wild? You sold Team Coco to SiriusXM earlier this year. Had you been seeking a potential sale, and why were they the right fit?For a while, we weren't seeking anybody. And then it started to become obvious that that was a possibility. Sirius, we were already involved because our podcast was through Sirius, and we had a meeting with them. They were terrific, and the message to us was: Don't change anything about yourself. Then they said, “Would you be interested in doing a SiriusXM channel?” I was like, “Could I do anything what I want with it?” And they said, “We want you to do whatever you want with it.” So I left that meeting thinking, "I really clicked with [SiriusXM president and chief content officer] Scott Greenstein and his team, but oh my god, it'd be so much fun to do this SiriusXM channel because it's going to feature all kinds of different content, not just from the podcast, but from years and years of doing comedy. And there's so much of it that would work well on the radio." I [also liked] that Sirius was interested in not hindering people's ability to hear us; if anything, trying to help us figure out ways for more people to hear what we're doing, for it to be more accessible. So people can still get the podcast the way they always did. But they can also, if they don't even know what we're up to, stumble across our channel at some point and maybe start laughing and we'll get them that way. So I guess the point of this article is there's no escaping me. And I mean that in the worst way. So I guess the point of this article is there's no escaping me. And I mean that in the worst way. You’ve alluded to what’s next for you a couple of times. When you announced your TBS exit, you said you’d be doing a show for HBO Max, but there haven’t been any new details about that in the past year. Where do things stand now?There was an assumption, and probably I assumed it, too, that I would leave the nightly show in late June 2021, and we’d let the dust settle, and then in September we’d start cranking up again. And that didn’t happen. Some of that was [because] I got really involved in the podcast company, and then we started talking to Sirius. But I can't say honestly that was the reason. I think there was some part of me that said, "We need things to settle a little bit. I don't want to get back out there, just to get back out there. I'd like to have a creative impulse that I think is worth people's time." HBO Max was very nice. I said, "Clearly, I'm going to need some time to figure this out." And they said, "Take your time." I don't want to say just yet what I'm thinking about, but we're starting to gear up. But in the meantime, I feel somewhat fortunate that we've taken our time because streaming is changing so much. When it was announced that I would go to HBO Max, the streaming business has gone through an entire revolution since then. And I would like to think that whatever we come up with is something that works in the new streaming reality. I don't want it to be antithetical to how TV works now. So I've been feeling lately like it was wise to take a little time and be patient about it, rather than immediately saying, “OK, here's what we're doing,” because it may not fit the current reality. One part of the current reality is that there’s been a lot of change within HBO Max, especially within unscripted. But you’re getting the message that whenever you’re ready, there’s still a home for you there?Like I say, nothing's been formalized. And there's no project as of this moment. But when it was in the news that HBO Max was terminating a bunch of projects, I had someone say to me, “Are you afraid they're gonna terminate your project?” And I said, “Well, we don't have one.” [laughs] I haven't gone into them with a pitch yet. So at the moment, I felt kind of snug and secure. "It's pretty hard to cancel something that doesn't exist!" That was in my best Jon Lovitz voice. Whatever I do end up doing for HBO Max, it only works if it works for both sides. And I'm sure we can figure out: What's their appetite? What do they want to do? Even after all this time, my ego isn't telling me, "They're going to do whatever I want to do because I'm Conan O'Brien!" That's not how I'm made. I have ideas of something I'd like to do, and we've had some really constructive talks. And so we will see. My hope is that we will be working on that this fall, and we can start to get it going. Even after all this time, my ego isn't telling me, 'They're going to do whatever I want to do because I'm Conan O'Brien!' That's not how I'm made. Do you feel less pressure around developing this HBO Max show now that the podcast business is thriving?I won't lie, it does take some pressure off because I have a great creative outlet. But I do miss aspects of television, and I still have an itch for that. And so figuring out how I fit into this—what's the evolution now?—and getting that right is still something that's important to me. So I'd love to get you and your readers off the hook and say, "Don't worry, you won't be seeing Conan on TV again." But something tells me that my ego and my fat Irish face will take control at some point. What do you still want to do that you haven’t done yet?Someday I'd like to play The Music Man's Harold Hill. I really just want to do the “[Ya Got] Trouble” song. There was an opportunity years ago for me to possibly step in when there was a vacancy in The Music Man [on Broadway] back in the 2000s. I was doing the Late Night show at the same time, and it became clear that wouldn't work. But, man, if there's a world where I could come out, tag in and do the "Trouble" song—I'm not sure I'm built for the whole musical—that would be my dream. I've been obsessed with it. I wrote a Simpsons episode that features a Music Man parody, [1993’s “Marge vs. the Monorail”]. It's been an obsession of mine for a long time. I think I am, at the end of the day, a vaudevillain. I love putting on a show, grease paint, people in horse costumes backstage and the crowds lining up. Is there anything else you want to share as you look back on your career?Something that I try to remind myself of is—because things are changing so rapidly and there's so much entertainment out there—my mantra is always: Don't be judgmental. Comedians are famously judgmental, [along the lines of] "I have very strong opinions about what's funny, or what's good. And this I think doesn't quite meet the standard." I just keep telling myself it's all changing so quickly. Don't calcify. Don't get stuck in your ways. Don't get judgmental. Be open to trying new things. Have some humility. And don't be afraid. I've been really blessed and had an amazing career, but I've also been through a lot of turbulence. I think what has helped me is there's some small part of me that always says, "OK, get up. Let's get back in there. Let's try again." I don't know if they teach that in business school, but I think that's so important to staying young and staying in the game. And I see these people: Mel Brooks. Norman Lear just turned 100. I'm lucky to be friends with Bob Newhart, and he'll be at my house sometimes, and he's still really funny. He's still really interested in making stuff and getting out there. Those are the people I admire. They weren't afraid to evolve, weren't afraid to keep trying and are still laughing and being silly and staying loose. And they probably have some evil potion they're drinking that they haven't told me about! Check out the rest of the 2022 Hot List here.

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Adweek Media Visionary Conan O'Brien Gets Sirius About His Audio Empire—and a TV Return

After reinventing late-night, the television icon is doing the same with podcasting

Jason Lynch

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Jason Lynch