“I really like making connections through comedy,” says Conan O’Brien, the beloved comedian who is now the dean of late night television hosts, having anchored a late night show for almost 27 years — NBC’s Late Night with Conan O’Brien from 1993 through 2009, NBC’s The Tonight Show with Conan O’Brien from 2009 through 2010 and TBS’s Conan from 2010 through the present — as we remotely record an episode of The Hollywood Reporter‘s Awards Chatter podcast. Indeed, O’Brien, who has maintained his trademark wavy coiffure through all of his years on the air, shut down Conan from Oct. 4, 2018, through Jan. 22, 2019, returning with a show shortened from an hour to a half-hour, and sans desk, band or suit, which allowed him to make more of his Conan Without Borders travel specials and to launch a podcast, Conan O’Brien Needs a Friend, which now routinely generates more than one million listens per episode. “I know that sounds a little pompous,” the 57-year-old continues. “But I love to make friends through comedy.”
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LISTEN: You can hear the entire interview below.
Past guests include Steven Spielberg, Oprah Winfrey, Lorne Michaels, Barbra Streisand, George Clooney, Meryl Streep, Robert De Niro, Jennifer Lawrence, Eddie Murphy, Gal Gadot, Warren Beatty, Angelina Jolie, Snoop Dogg, Jessica Chastain, Stephen Colbert, Reese Witherspoon, Aaron Sorkin, Margot Robbie, Ryan Reynolds, Nicole Kidman, Denzel Washington, Julia Louis-Dreyfus, Matthew McConaughey, Kate Winslet, Jimmy Kimmel, Natalie Portman, Chadwick Boseman, Jennifer Lopez, Elton John, Judi Dench, Quincy Jones, Jane Fonda, Tom Hanks, Amy Schumer, Justin Timberlake, Elisabeth Moss, RuPaul, Rachel Brosnahan, Jimmy Fallon, Kris Jenner, Michael Moore, Emilia Clarke, Lin-Manuel Miranda, Helen Mirren, Tyler Perry, Sally Field, Spike Lee, Lady Gaga, J.J. Abrams, Emma Stone, Al Pacino, Julia Roberts, Jerry Seinfeld, Dolly Parton, Will Smith, Taraji P. Henson, Sacha Baron Cohen, Carol Burnett and Norman Lear.
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O’Brien is one of six children born in Brookline, Mass. to an epidemiologist and a lawyer, and raised observantly Irish-Catholic. An anxiety-riddled youngster, he found some relief watching Johnny Carson with his dad, and then discovered David Letterman through his older sister, en route to gaining acceptance to Harvard and becoming the first two-term editor of the Lampoon, the university’s humor publication, since Robert Benchley did so in the early 20th century. Fun fact: The editor of the Crimson, the university’s daily newspaper, who once had him handcuffed by police over a prank, was none other than Jeff Zucker, who years later would clash with O’Brien over The Tonight Show. “It really is kind of akin to if General Lee and General Grant had been playing pranks on each other at West Point, and then later on got involved in this epic Civil War,” O’Brien cracks.
Upon graduating in 1985, O’Brien and fellow Lampoon staffer Greg Daniels (who would later adapt The Office for American TV) decided to team-up and head to New York to pitch their comedy wares. They landed a TV writing gig that brought them out to Los Angeles, whereupon O’Brien dabbled in performing for the first time by taking improv classes at The Groundlings Theatre & School. But it was writing that brought O’Brien back east (he worked at Saturday Night Live from 1988 through 1991) and then out west again (when, within days after quitting SNL, he was offered a position writing for The Simpsons, which he did from 1991 through 1993).
In 1993, the late night landscape suddenly shifted. Johnny Carson announced he was retiring from The Tonight Show. Jay Leno was hired to succeed him over David Letterman, host of Late Night, the show that followed The Tonight Show, who then left for CBS. And SNL chief Lorne Michaels was tasked by NBC with finding a replacement for Letterman. Michaels initially reached out to O’Brien about serving as a producer of the still host-less show, but O’Brien didn’t feel right about it and withdrew his name from consideration. Later, after flirting with Larry Sanders for the hosting job, Michaels came back to O’Brien, this time for that post, and O’Brien said yes. It was a big gamble for both parties, since O’Brien was completely unknown to the public and inexperienced in front of a camera.
When O’Brien’s Late Night debuted, and for quite a while thereafter, the reviews were not kind. Aiming to distinguish himself from Carson and Letterman, he decided to try “something kind of post-modern” and “not about irony and detachment” — and got slammed for doing so. “That was very, very, very intensely painful, and it comes back to me sometimes,” O’Brien acknowledges. “I’ll still have nightmares about that time.” But, with time, his abstract, cartoonish, self-deprecating came to be accepted, and he settled into a groove. “I had to learn my job and the audience had to learn my rhythm, and then we met in the middle.”
For 16 years O’Brien hosted Late Night, the last five of which he did under the assurance that he would subsequently succeed Leno as the host of The Tonight Show, O’Brien’s dream perch. Leno had reluctantly agreed to that timeline, but, as the clock ran out, decided he did not want to retire after all, as he remained atop the late night ratings; NBC, meanwhile, did not want to cut him loose, as he would have signed with a competitor and gone head-to-head against O’Brien.
“I knew things were going off the rails and that we were in a weird position before we even took over The Tonight Show,” O’Brien says, “because before we did they announced that Jay Leno would move to 10 o’clock and do an hour there every night — essentially, The Tonight Show with Jay Leno would be from 10 to 11, then there would be local news from 11 to 11:30, and then The Tonight Show with Conan O’Brien would start — and this was before we had done anything. We hadn’t even moved out yet. We were still doing Late Night shows. And I think that that’s when I thought, ‘What?!'” He likened NBC’s position at that time to “a restaurant that serves you an ice cream sundae, and then for dessert you get an ice cream sundae.'”
Things only got worse from there. O’Brien’s ratings at The Tonight Show were not what had been hoped for — some at the network suggested this was because his sense of humor did not play as well at the earlier hour, whereas O’Brien allies suggested this was because Leno was not delivering a strong lead-in. “And then I knew it had really gone off the rails,” O’Brien elaborates, “when the 10 o’clock thing with Jay imploded and they said, ‘Okay, here’s what we’re gonna do: we’re gonna still keep both of you, but we’re gonna move him to 11:35 and we’re gonna put you on at 12:05 but still call it The Tonight Show, even though technically now it’s tomorrow.’ And that’s when I said, ‘You guys can’t seem to do this [to terminate O’Brien’s relationship with the network], so let me do it for you.’ And I’ve never regretted that. It was very clear to me then, and it’s very clear to me now, that no one was leading anything, no one was making the decisions that had to be made, so I said, ‘This is what I’m gonna do.’ And I did it in a way that I stand behind and I’m proud of.”
Indeed, O’Brien’s final episodes of The Tonight Show revealed that he possesses a passionate and fiercely loyal fanbase — which has come to be known as ‘Team Coco,’ after a nickname given to O’Brien around that time by Tom Hanks, and which now includes 28.5 million people who follow him on Twitter, more than any other late night host except Jimmy Fallon — who felt that NBC and Leno had acted dishonorably toward O’Brien. O’Brien, for his part, ended his Tonight Show run with a powerful message that has since appeared everywhere from T-shirts to spraypainted walls: “I’m asking this particularly of young people that watch. Please do not be cynical. I hate cynicism; for the record, it’s my least favorite quality. It doesn’t lead anywhere. Nobody in life gets exactly what they thought they were going to get. But if you work really hard, and you’re kind, amazing things will happen.”
O’Brien, who reportedly received a $32 million settlement from the network that came with a brief non-compete clause, then powered through a period of depression by embarking on a live performance series cheekily entitled The Legally Prohibited From Being Funny on Television Tour. He recalls, “I thought, ‘I’ll just be myself and I will do my show on a desert island if I have to, but it will be me and it will be what I want to do.’ And that has proven to me to be the course that brought me the most happiness.'”
After his tour wrapped, O’Brien signed a deal to host a late night show for the cable network TBS. Conan debuted in late 2010, and evolved nicely over the next eight years, at which point O’Brien decided to rejigger the show and focus more of his time on his travel specials and podcast. “I’ve always loved ‘evergreen’ comedy,” he says by way of explaining what draws him to those projects outside of the traditional late night format. “I think I’ve been funny [on them] in a way in a way that, if you look at it in 30 years, still might make you laugh.” As for his longer-term future? “I can keep doing it as long as it keeps changing and it’s interesting to me,” he insists. “I am having as much fun, and probably in some ways more fun, now than I’ve had before. And as long as that’s true, I’ll keep doing it.”