Inside Conan O’Brien’s Digital Reinvention

When he’s not hosting his late night show, Conan O’Brien likes riding his mountain bike through the Hollywood Hills. He was recently peddling up a hill when he spotted a group of teenage BMX bikers doing tricks. He paused to let them pass, but they stopped after spotting O’Brien. “They’re like, ‘Conan, man, oh snap!’” O’Brien says. “They really didn’t say that. No one says that anymore. But they really wanted to talk to me. I kind of wanted to say, ‘Do you know how old I am? Look at this rotting pumpkin head.’ But it really doesn’t matter to them.”

O’Brien told the story Thursday during an onstage conversation with CNN’s [ke Tapper in New York. 25 years into the late night game, O’Brien is hyper-focused on appealing to kids like these; he believes they saved his career after he lost the Tonight Show in 2010. “I have a lot of fans now that weren’t born when I went on the air. They don’t know the old references … what they’re passionate about is the stuff that we’ve done in the last three years. That’s exciting to me.”

O’Brien is cutting the length of his TBS late-night show to 30 minutes in 2019, but he is doubling down on his digital output. This includes a podcast, Conan O’Brien Needs a Friend, which starts November 19th and will feature O’Brien talking with guests including Kristen Bell, Bill Burr, Wanda Sykes and more, and an online archive of more than 4,000 episodes that will launch in January. O’Brien is also planning to release footage of his office life around the clock online. “Part of what we’re trying to do in this new shift is you should be able to see what I’m up to almost 24 hours a day,” O’Brien says. “If we have something funny, we could comment on in the moment; that should be put out there at three in the afternoon. You shouldn’t have to wait until a linear show.” O’Brien says he’s done with the old approach: “I’m here behind my desk, this is what I’ve prepared, this is my first guest, my second… goodnight – it doesn’t make any sense anymore.” Here are nine things we learned from O’Brien’s conversation with Tapper.

1. He doesn’t want to get too political. Since 2016, late night television has become defined by politics. O’Brien admits he often wonders, “am I supposed to be doing more of that?” But ultimately, he doesn’t see that kind of topical material as his strength. “Something that’s benefited me … is making things that are silly and funny in more of a timeless way,” Conan says. He adds that this is a big reason his old bits have found new life online. “The Triumph [the Insult Comic Dog] Star Wars remote is as funny as it was 15 years ago … I’m trying to manufacture more of those. I think the best moments from my travel shows will still be funny long after I leave this earth, in nine years – it’s a long story.”

2. He recently “rented a family” in Japan. O’Brien’s hit Conan Without Borders series has taken him to Cuba, Italy, Haiti, Mexico, Israel and, most recently, Japan, where he filmed what he calls one of his favorite bits of his career. “You can rent a family in Japan if you’re lonely,” O’Brien said. “It’s not a creepy thing; there are services for people who want companionship. It does sound creepy, but it’s something that’s really part of the Japanese culture. So I rented a family: a wife, husband, a daughter. I made my Japanese father apologize for things my [real] father had done in the Seventies. This man doesn’t speak much English and I’m making him apologize for the time he yelled at me for spilling creamed corn on the linoleum floor in 1975. And he’s apologizing to me very sincerely, and I felt like I had a breakthrough with my dad. It’s one of the weirdest thing I’ve ever shot. And that’s just the tip of the iceberg.”

3. He has advice on how to be a good guest: “Be funny,” he says. “Get out there and be really funny and create a great moment and I’ll make sure we plug what you’re doing. If you spend the whole time saying ‘Listen, I’ll get to that, but first I want to say, ‘What an incredible cast….and some of the pranks behind the scenes, I gotta tell ya’ – those are the guests I want less and less of, because they drive me crazy.”

4. He critiques his old hosting style. “It’s funny to look at a tape from ’93 now,” he says. “Because they do look like they’re from the late Forties. First of all, I look like a 28-year-old Belgian woman – and in a good way. I’m so young, so inexperienced and I’m trying to do a good job. I’m shaking peoples hands and I’m sort of moving how people do in 1930s news reels. I look at it now and realize that, over time, my hosting style became much more, ‘forget the rules.’ If something interests me in the moment, drop everything and go for that. [Audiences] know when something’s real and when somethings been rehearsed 10,000 times. They can sense it.”

5. He riffed on the differences between his old fans and new ones. During his years hosting Late Night With Conan O’Brien, he says that conversations with fans usually went the same way: “They usually gave me an explanation first as to why they were up that late. They would say, ‘I saw what you did last night. See, I have this rash and have to put this cream on. It has to be every two hours, so I had to get up’ … And I’m like, ‘I don’t want to know any of this right now.'” His new fans don’t even own TVs. “There’s a whole generation that expects to see their media that way. They expect to see it on their phone, on their tablet, on their computer … They don’t watch SNL the way we watch SNL. They’re looking at the clips throughout the week. When I come into the office all the young people are looking at clips of all the different late night shows and seeing it on their time. The good news is, if the work is good, it’s going to be seen. That’s what I love.”

6. Tapper felt tapped out. At one point in the conversation, Tapper took a sip from a Starbucks iced coffee, causing Conan to remark on his “very fertile sip.” “I haven’t gotten a lot of sleep this week,” Tapper said, referencing the midterms. “Well, you probably couldn’t sleep because of this thing,” O’Brien said. “This is a big moment for you, Tapper. This is make or break for you.” He broke into a Tapper imitation: ‘I’m gonna speak with Conan soon [and] we’re gonna talk about platforms! I can’t sleep. What he’s doing in the digital space is crazy!’”

7. He has a theory why there are no more late night wars. An audience member asked O’Brien why, with more late night hosts than ever, there are no more rivalries like in the Leno-Letterman days. “I hate them all,” O’Brien joked of his competitors. “They’re all pricks … first of all, who knows what comedians are really thinking. But I think that there’s no percentage in it anymore. For a long time there was one host: Johnny Carson. And he really was it. Then suddenly overnight there’s two. And it was very controversial the way it all went down, so there was going to be bad blood, and then the media plays into that because the media loves a horse race. I think it’s very difficult with as many shows as there are right now. There’s 135 horses running. The media used to be able to report on, ‘Jay just pulled ahead’ or ‘Letterman’s up now.’ I don’t think there’s a storyline there now. There’s so many shows, ratings are complicated, networks can use different metrics. It’s not a fun story.”

8. He has an analogy for the new half-hour format: “I say I prefer [to call it] smaller cookie, more chocolate chips. What I want to make clear about the 30-minute show is it’s still me. It’s still me being funny, so this is not ‘check out the whole new Conan’ because there’s no such thing … I just feel energized. I feel very fortunate to be in this stage where I’ve been doing it for 25 years and I think I’m having more fun in some ways now than I ever have before.”

9. His goal for the half-hour format? “Informality.” O’Brien is vague about what his new half-hour format will look like. “It’s a radical change for me,” he said. “It’s going from 44 minutes to 22 minutes. And that is going to be an adjustment. It’s going to change the style and the flow of the show.” When Variety asked Conan for specifics, he said he’s still working it out.  “There’s a lot I do know. The band will not be there. I’m looking for something that has a little bit more of an informality to it. I’m very interested in bringing the audience even closer and pushing me into the thick of it.”

O’Brien says he’s planning on shooting for longer than 30 minutes, editing it down for TV and posting the full show online, along with behind-the-scenes bits like audience Q&As. “In some ways, I’ll be working less hard, and in some ways I’ll be working harder,” he says. “What I really like is it to feel like I’m playing. I’ve done the 25 years I’m really proud of the work. And now it’s time to try to break it: try to have fun and play with the conventions. I really want to go with informality: moments I think are great, and make sure you never see me running out the clock. If you see me for a second running out the clock, then I did not do my job.”