THE VERY FIRST moments of Conan O’Brien’s short reign as host of “The Tonight Show” were soundtracked by one of his favorite songs. That inaugural episode in June 2009 started with a taped segment — goofy, funny and random, in typical O’Brien fashion — of the host running from New York to Los Angeles to his dream job with Cheap Trick’s “Surrender” as the musical accompaniment. When O’Brien exited as host just seven months later, he lost not only a show, but also a song. He couldn’t listen to “Surrender” anymore. Every time it came on the radio, he quickly changed the station. The song was a reminder of the debacle that threatened to derail his career.
Note: Above: Conan O’Brien on the set of his TBS late-night show. (Brinson + Banks for The Washington Post)
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Except his career turned out to be fine. The past couple of years have had so much upheaval in the ever-expanding realm of late-night TV that it’s easy to overlook this significant fact: O’Brien is now the longest-tenured host of them all. He still has the same boyish looks as when he debuted in 1993, so some forget that he has been doing this for more than two decades. For the past five-plus years, he’s been on TBS, where “Conan” has carved out an incredibly devoted — and young — audience as he has struck the ideal balance between the vintage silliness that made him a cult favorite on “Late Night” in the ’90s and the Internet-era virality that is required today.
Recently, O’Brien was driving in his car and “Surrender” came on the radio. But instead of changing the station, an involuntary reaction at that point, he cranked up the volume.
O'Brien, who has been a host for 23 years, peeks out from behind his set curtain. (Brinson + Banks for The Washington Post)
O’Brien has just wrapped a comedy bit for “Conan” that involved him smashing the hell out of a Jeep with a baseball bat. It’s completely out of character for the real Conan, which means it’s completely in character for the TV version of himself, who sometimes adopts the comically deranged persona of an old movie villain. The bit occurs just beyond the Warner Bros. lot, and it takes only a few minutes outside on a hot, sunny January day like this to make him acutely aware that his pale, 100 percent Irish skin will never adjust to living in Los Angeles.
“We’re near the Mexican border, and I’m genetically engineered to live in a bog,” he says.
As he walks back toward the “Conan” studio, a shuttle packed with tourists rolls by and the driver slams on the brakes so the passengers can get a glimpse of a Real Live Celebrity. They gasp and scramble for their phones to snap a picture. O’Brien gives a polite wave and calls out, “It’s all lies!”
Quick-witted and absurd, it’s kind of a perfect Conan mini-moment. And now those moments are happening all over the world. The 52-year-old host has gone continent-hopping, filming recent episodes of his show in Cuba, Qatar, Armenia and South Korea. Foreign adventures have been a staple of his show — his 2006 visit to Finland to meet his doppelganger, President Tarja Halonen, is perhaps never to be surpassed — but the pace at which O’Brien is racking up the frequent-flier miles is surprising given the typical arc of talk-show hosts.
In the early days, hosts will go anywhere and do anything for a laugh. Eventually, as they become established, they become anchored to their desk. But slowing down isn’t in O’Brien’s nature. He is “so energetic, it’s kind of nerve-racking,” says comedian Norm Macdonald, a longtime friend.
“I’m hungry like a vampire that’s feeding off anything that will make me feel like I’m still doing this for the first time,” O’Brien says later. “At this stage of my life and career, I’m just obsessed with really having fun and having new experiences and maybe getting to be funny in a slightly different way.”
O’Brien also doesn’t have the luxury of taking it easy. Even as the elder statesman of late-night television, he has seen things get only more hectic as the digital landscape has turned the industry upside down. When O’Brien was on “Late Night” at NBC, his main competition was Tom Snyder and his long-form, intellectual one-on-one interviews. These days, O’Brien shares a space with the likes of Jimmy Fallon, Stephen Colbert, Jimmy Kimmel, Seth Meyers, James Corden, Trevor Noah, Bill Maher, John Oliver, Larry Wilmore, Samantha Bee . . .
“What does it mean that there are literally more talk-show hosts than active jurors in America right now?” O’Brien jokes.
Oddly enough, he says, it’s “liberating” to have so many competitors and he’s embracing the changes in the industry. If anything, it has given him license to indulge in ideas that are uniquely his.
“The international stuff and focusing more on the remotes has probably resulted in me feeling less pressure to be like: ‘America needs a Marco Rubio joke tonight, or a Donald Trump joke tonight, and it’s my job to supply it!’ ” O’Brien says. “I know it seems counterintuitive, but when I began in 1993, there were so few [hosts] that everything was a huge deal. . . . Now you feel like you’re able to focus more purely on: ‘What is it that I really want to do with this time? What’s important to me?’ ”
Conan O'Brien's favorite things
BACK IN THE “CONAN” OFFICES, O’Brien has received some great news. Something very rare has happened — he made it into the tabloids. And it’s a whopper. A staffer hands him a page of Star magazine that boasts a quote from his assistant, Sona Movsesian: “Conan’s right hand [Sona] has heard it all from the off-the-wall funnyman. ‘Conan often has long conversations with himself in the mirror,’ the gal Friday admits.”
This launches O’Brien into an extended riff where he plays into the obviously fake factoid, cracking up every staffer (especially Sona) in his proximity. His mirror chats aren’t conversations, he protests, but more “Mussolini-esque tirades” than anything.
“He toggles between smart and really goofy. And as he’s gotten older, he’s really fine-tuned that craft,” said TBS President Kevin Reilly. “The ability to toggle back and forth into situations and cultures and different situations — that’s why these out-of-studio pieces have hit a new high for him.”
O'Brien often plays guitar during the show's rehearsals. Here, he celebrates George Harrison at a music event in 2014. (Frazer Harrison/Getty Images)
This particular strength comes up often in the debate about what is and isn’t funny on late-night TV, which has moved beyond the standard monologue-sketch-interview formula to include a deluge of games, stunts, karaoke and lip-syncing.
“Everybody has taken Jimmy Fallon’s lead in terms of ‘do something that goes viral’ and do a talent thing, rather than comedy being the primary objective,” Macdonald says. “I think with Conan, still the first agenda is comedy and everything comes after that.”
But you’ll never hear O’Brien compare himself to anyone else. He insists it’s a pointless exercise. His collaborators are also loath to criticize competitors, saying there’s room for everyone. In a rare move last year, O’Brien publicly chastised one of his writers who tweeted a screed against the “prom king comedy” favored by Fallon and Kimmel: “Comedy in 2015 needs a severe motherf—ing shakeup. No celebrities, no parodies, no pranks, no mash-ups or hashtag wars . . . and shove your lip-synching up your ass.”
“I wish one of my writers would focus on making my show funnier instead of tweeting stupid things about the state of late night comedy,” O’Brien tweeted in response.
“I do not like comedy snobbery. I do not like people passing judgment on other people’s comedy, especially publicly . . . there’s tons of stuff out there that we can choose to dislike,” O’Brien says now.
And it’s not like O’Brien doesn’t love a good stunt with a celebrity guest. He has eaten Taco Bell with Martha Stewart and joined Grindr with Billy Eichner. But you will not find him playing any games. Mostly because he doesn’t like them. If someone invites him over to play “Pictionary,” he’ll find a way out of it.
“I don’t have anything personally against anyone doing that. That’s just not my thing, and it wouldn’t be organic. It wouldn’t look right,” O’Brien says. “I don’t want to make Dame Judi Dench ride a pogo stick. If Dame Judi Dench shows up and says, ‘By the way, I happen to love riding my pogo stick,’ great! But I don’t want to make her ride a pogo stick. Because when she falls, then we’re at war with Britain and it’s my fault.”
WHEN O’BRIEN WAS A WRITER on “The Simpsons” early in his career (he wrote the classic “Monorail” episode, among others), creator Matt Groening noticed something: He was happiest when he was performing. This wasn’t a trait shared by most writers.
“Conan would be sitting over in the corner [of ‘The Simpsons’ writers’ room], doing his own little show with office supplies, staplers and tape dispensers,” Groening says. “Then when he got caught, he would mime getting into an invisible rocket ship . . . and escaping. It was a very good mime, very convincing.”
After David Letterman moved on from his 12:35 a.m. gig on “Late Night,” O’Brien’s former boss, “Saturday Night Live” honcho Lorne Michaels, recommended that O’Brien audition for the host. Michaels saw those same performance tendencies that Groening did during O’Brien’s time as a writer for SNL from 1987 to 1991. No one was more stunned than O’Brien when he — a 30-year-old virtual unknown — actually got the job to replace the already iconic Letterman. Groening remembers O’Brien got the phone call with the news in the middle of a Monday morning “Simpsons” table read. He left to take the call and never came back.
“Late Night” started out rocky. NBC renewed it in 13-week spurts, just about the minimum amount of confidence the network could show. Former Washington Post TV critic Tom Shales famously eviscerated the show in the beginning, calling it “an hour of aimless dawdle masquerading as a TV program” and saying that O’Brien “is a living collage of annoying nervous habits. He giggles and titters, jiggles about and fiddles with his cuffs. He has dark, beady little eyes like a rabbit. He’s one of the whitest white men ever.”
Eventually, things stabilized and O’Brien captured the college crowd, delighting younger viewers while being as weird as humanly possible. In 1996, Shales wrote a mea culpa and deemed the show “an inspired absurdist romp,” calling O’Brien’s evolution “one of the most amazing transformations in television history.” Through the ’90s, O’Brien and his staff developed an array of reliably hilarious characters and bits, be they random (satellite TV channels — who remembers “Not Cool, Zeus”?), visually disturbing (If They Mated), or random and visually disturbing (the beloved Masturbating Bear).
“It was just an incredible place because I think they used that premise of ‘Gosh, no one’s really watching, so we may as well screw around’ to the fullest advantage,” says Will Ferrell, another longtime friend of O’Brien.
Strange ideas were encouraged. Jack McBrayer, the “30 Rock” star who started out playing various characters on “Late Night,” remembers being dressed up as a VHS of “Hope Floats” that was shot by bandleader Max Weinberg. “We went into this stretch where I would be shot or killed or beaten up very consistently,” McBrayer recalls. “Like, extremely consistently.”
ON HIS SHOW, O’Brien has always alternated between extreme self-deprecation (describing his aging process as “watching a melon rot in the sun”) and inflated egomaniac boasting about his fame. During monologues, he’ll deliver joke after joke about his flaws — though one of his writers, Laurie Kilmartin, admits that sometimes he’s not so thrilled if they pitch him jokes three days in a row about how unsatisfying he is in bed.
“You don’t have to figure him out; when you see him you’re comfortable right off the bat,” says Deon Cole, a former writer. “He is what he is as soon as you see him.”
His staffers rave about his lack of ego and how he quickly transitions from “famous person” to a regular guy with a wife and two kids at home. Although sometimes O’Brien’s humility can be a detriment. He admits he’s a terrible salesman.
Conan O'Brien and his wife, Liza, at the 2016 Vanity Fair Oscars party. (Adrian Sanchez-Gonzalez, AFP/Getty Images)
“I’m not here to say, ‘You’ve gotta check out me, see, I’m the bee’s knees! I’ve got it all, I’m Conan O’Brien!’ I’ve never had that instinct,” he says.
That was one of the issues NBC had with his version of “The Tonight Show.” O’Brien’s wacky humor and habits didn’t necessarily mesh with the show’s built-in crowd of older, more conservative viewers, and he didn’t adhere to suggestions on how to endear himself to a new audience. His ratings fell, and Letterman’s CBS “Late Show” jumped into first place.
The combination of O’Brien’s resistance and sinking viewership upset NBC. When the network decided to move “The Tonight Show With Conan O’Brien” to 12:05 a.m. to make room for a half-hour Jay Leno program at 11:35 p.m., O’Brien refused, saying moving the start time would be destructive to the historic franchise. The clash made worldwide headlines as NBC eventually bought him out of his contract for a reported $32 million. O’Brien’s departure from “The Tonight Show” may have made him seem like a failure to some, though it unquestionably made him a cult hero to a significant group — Team Coco, they dubbed themselves — that cheered him on for his integrity and raged against NBC’s short-sightedness.
“Conan really represented our comedy, our kind of viewpoint, our comedic style for a whole generation of comedians,” Ferrell says. “And NBC in a sense was basically saying: ‘Nope, this doesn’t work. You guys aren’t funny enough for this slot.’ They just weren’t giving it enough time to develop and find its footing, and it felt like a real kind of slap in the face.”
“There was a period of my life, it probably lasted at least two years, where I was just trying to wrap my mind around . . . ‘What the f— happened there?’ ” O’Brien says. “Now enough time has gone by, and a big part of the process of getting over it was making new stuff I was proud of. I think if I had left show business after that, I’d be a muttering crazy man. But the fact I was able to immediately go back into what I really love, and working with people I love working with — now I rarely think of it.”
Comedian Will Ferrell, seen here on 'Conan,' is one of O'Brien's favorite guests. (TBS)
COMING TO TBS was a breath of fresh air, especially given that the show has what employees describe as “free rein” since it debuted in November 2010. The network loves that O’Brien draws the youngest median age (about 42 years old) of any hour-long late-night show, the most important demographic to advertisers.
“That’s amazing. That’s actually amazing,” says Bill Carter, a former New York Times TV reporter who has written two books on late-night TV. “NBC would have said that was his problem, he couldn’t cross over into the biggest audience . . . which was mainstream. That was their point. On TBS, maybe they don’t care.”
Before Reilly started as TBS president in late 2014, he sat down with O’Brien and Ross to talk about ways they could improve the show — he felt O’Brien was “toiling a little bit in obscurity,” as he told the Hollywood Reporter.
What happened next was the travel spree, which Reilly enthusiastically agreed to after he took over TBS. Once Reilly saw the footage from Cuba — where O’Brien danced with locals, toured a rum factory and took Spanish lessons (“How do you say ‘I am America’s biggest star?’ ” “And how do I say ‘Don’t check on that, don’t look into it, just trust me?’ ”) — Reilly told them to go wherever they wanted next.
O’Brien’s penchant for adventures also translates quite well to the digital world. Earlier this year, the show’s YouTube channel surpassed 2 billion views. Since January, about 31 million people have watched Kevin Hart and Ice Cube help O’Brien teach his staffer how to drive, the most popular video in the show’s history.
Reilly acknowledges that, obviously, he would love it if he could wave a magic wand and turn these online viewers into people who watch the show on television, where he could monetize it. This year, “Conan” has averaged 748,000 total viewers a night, up 12 percent from the final quarter last year. About 60 percent of viewers are 18 to 49, the key demo. By comparison, Comedy Central’s “The Daily Show With Trevor Noah” has averaged 1.4 million viewers and 48 percent of viewers in the 18-to-49 age range. The highest-rated late-night show is “The Tonight Show Starring Jimmy Fallon,” with 3.6 million viewers and 35 percent in that coveted demographic.
As the network looks for ways to embrace O’Brien’s huge online audience, it also looks realistically at how people are watching.
“There’s no more ‘Tune in at 11 o’clock!’ — [that’s] almost like the wheeze of a dinosaur,” says Andy Richter, O’Brien’s announcer/sidekick. “Tune in? Nobody tunes in at 11 o’clock. I mean, they do, but it’s not what anyone cares about, that’s not the way it’s going. So we have had to adjust in that we have to think of things that are very emailable or clips that are easily pulled and put on a website.”
“When Conan goes out of the country, people quote bits of his — clearly they have not watched at 11 on TBS,” Reilly says. “We don’t know if, ultimately, a show evolves more of that and less of a formatted talk show.”
“This year, I think he’ll take the new step forward, more of the videos, more of the outside-the-studio stuff . . . and see where it leads to.”
Conan O'Brien is the first late-night host in 50 years to film a show in Cuba. The comedian has been increasingly continent-hopping and filming shows abroad. (TBS)
THERE IS NOTHING O’Brien loves more than freelancing off his own material.
“Kim Kardashian and Kanye West say they will have no more children,” he said during a recent monologue when the crowd suddenly interrupted and exploded into loud applause.
O’Brien jumped a bit, his hand covering his face as he tried to suppress a grin. “Don’t do that — that’s a horrible reaction!” he said as the crowd clapped louder. “How do you think their children now would feel?!”
“You people are cold,” agreed Richter from the sidelines.
“My God,” O’Brien said, trying to recover. “How am I supposed to do a joke now?”
“Well, it’s already up there on the card,” Richter explained.
He finished the joke (the punch line: “They said all the really terrible names were already taken”), but it was the riffing that became the most memorable part of the exchange. O’Brien so embraces and owns those delightfully awkward moments that it’s sometimes hard for him to remember when things actually were that awkward and everything that has happened since.
“I have a picture of me with Johnny Carson in 1993; we’re both wearing silver suits with red ties, which is just an accident. We’re both laughing, and I look like a 14-year-old girl,” O’Brien says, smiling at the memory. “I love that photo because I look at that sometimes and think: ‘You have no idea what you’re in for. But it’s all going to be fine. It’s going to be bumpy, but it’s going to be fine. And you’re going to have a lot of fun.’ ”
O'Brien checks himself out backstage at his show -- and clearly likes what he sees. The host's staffers say he is actually down to earth and doesn't have an ego, but O'Brien often jokingly acts the opposite when he's on TV. (Brinson + Banks for The Washington Post)