NEIL GRABOWSKY
Stephen Colbert interviews Conan O’Brien at NJPAC in Newark, Dec. 7, in a benefit for Montclair Film.
Conan O’Brien has an Emmy-winning HBO Max travel show (“Conan O’Brien Must Go”), a budding acting career (“If I Had Legs I’d Kick You”) and a highly successful podcast that SiriusXM bought as part of a $150 million deal (“Conan O’Brien Needs a Friend”). Earlier this year, he was honored with the Mark Twain Prize for American Humor and inducted into the Television Academy Hall of Fame. He is hosting the Oscars for the second consecutive time in March. A series he produced (“The Beast in Me”) has also just been nominated for several Golden Globes.
Not too shabby for a guy who hosted the last episode of his late-night show in 2021.
But it could have all been over for him decades ago, not long after he got his big break. And that wasn’t the first time he thought he was finished — that his luck had run out.
NEIL GRABOWSKY
Conan O’Brien at NJPAC.
“It’s so funny how many times in my life I thought ‘Well, that’s it,’ ” O’Brien, 62, told a sold-out crowd at Montclair Film’s annual benefit at NJPAC in Newark on Dec. 7.
“I think about this a lot,” he continued. “That’s the one piece of advice I would give to younger people … if you stay in the game and just tread water, eventually things will change and things will get better and I’ve seen it happen to me maybe at nine different points in my life, where I just was convinced a steel door has come down, this isn’t going any further, it’s not gonna happen and I will not advance, I will not get to do what I wanna do. I was heartbroken. I look at those moments now and realize that I was being diverted into a different path and, eventually, what ended up for me was much better.”
O’Brien, who spent 28 years in late-night TV, was in Newark for an onstage conversation with Montclair’s own Stephen Colbert, 61 — whose decade-long run as host of “The Late Show” is set to end in May, along with the show itself.
Any notion of things being “over” for O’Brien might conjure scenes from 2010, during the botched late-night succession at “The Tonight Show,” which saw O’Brien leave his new post there and previous host Jay Leno return. (O’Brien would go on to host “Conan” on TBS.) But that definitely was not the first time O’Brien felt a steel door coming down.
When he was the 30-year-old host of “Late Night with Conan O’Brien” in 1993, he had the daunting task of introducing himself to a skeptical audience after David Letterman left NBC to start “The Late Show” on CBS.
When Charlie Rose interviewed O’Brien about his gig as the new face in late-night, Rose read top Washington Post TV critic Tom Shales’ withering review of the show. O’Brien hadn’t seen the article yet. (Hearing this, the NJPAC audience let out a collective “ohhhh.”)
NEIL GRABOWSKY
Conan O’Brien and Stephen Colbert at NJPAC.
The color drained from O’Brien’s face when Rose read the review. The damage was done. Later, Shales would revise his assessment of “Late Night with Conan O’Brien” and call it his favorite late-night show.
But even before he was named the “Late Night” host, O’Brien contended with a major rejection. “My dream was to write for David Letterman’s late-night show (“Late Night with David Letterman,” the show he later took over), and I thought it was my destiny, and I saw what Chris Elliott was doing, and I said, ‘I could write that stuff,’ ” he said.
It was down to O’Brien and someone else. He did not get the job. “I thought, ‘That’s it,’ ” he said. “I believed it, and if someone had told me, ‘No, it’s not,’ I’d have yelled at them.”
O’Brien’s first job as a comedy writer in Los Angeles was for the HBO sketch series “Not Necessarily the News.” He booked the show alongside his friend and roommate Greg Daniels, a fellow Harvard alum who would go on to develop the American version of “The Office” and co-create series like “King of the Hill” and “Parks and Recreation.”
Both had to find new jobs after they were laid off from the show. O’Brien opted for Wilsons House of Suede & Leather, where his boss had no idea he was a comedy writer. He later left to write for “Saturday Night Live” in New York, putting him on a path to late-night before he got hired on “The Simpsons.”
O’Brien was not exactly champing at the bit to audition for the “Late Night” host job. However, something said by Michelle Saks Smigel (his friend Robert Smigel’s wife) made him try anyway: “What do you have to lose?”
(The Smigels, who were in the audience at NJPAC, got their own round of applause. Robert Smigel, a former “SNL” writer, became the head writer for O’Brien’s “Late Night.”)
NEIL GRABOWSKY
Stephen Colbert interviews Conan O’Brien at NJPAC.
Lisa Kudrow, who was then dating O’Brien, helped him get ready for the host audition by giving him a white linen “Don Johnson” jacket that didn’t exactly flatter his skin. For his tryout, he interviewed Mimi Rogers and “Seinfeld” star Jason Alexander. All fun and no pressure, since he didn’t think he had any chance.
But when O’Brien received the news that he got the job, he wasn’t ecstatic, he told Colbert. “I was terrified.”
He knew how hard it would be to create something people would want to see in Letterman’s old time slot. In the early days of his show, O’Brien contended with the constant reality that he could be ejected as host.
He remembered going to a therapist and telling them he felt like a fraud, like NBC picked the wrong host. When the therapist said those were just thoughts, not reality, he produced a copy of USA Today that proved otherwise.
“You know what would’ve made it better?” Colbert told him. “If you hired me.”
Colbert did apply for a writing job years ago at “Late Night With Conan O’Brien,” but he wasn’t hired, echoing O’Brien’s experience trying for Letterman’s “Late Night.”
It’s something the “Late Show” host reminded O’Brien of more than once during the conversation. (O’Brien noted that Ray Romano also tried to get a writer job at the show before “Everybody Loves Raymond,” but was turned down.)
O’Brien shared his belief that even though Colbert’s professional future is now uncertain, beyond May, “There isn’t a person in this world who’s worried about Stephen Colbert.”
NEIL GRABOWSKY
Stephen Colbert at NJPAC.
In an introduction featuring Gov.-elect Mikie Sherrill, current Gov. Phil Murphy said he told Colbert he would make a good candidate for elected office as a valued resident of the People’s Republic of Montclair (like Sherrill).
“We’re both about to be out of a job,” the outgoing governor said, referring to CBS and Paramount’s decision to end “The Late Show.”
O’Brien said he is sad to see late-night TV fading away, but has hope in young comedians. “I believe that humans find a way and really funny people who are 15, 16, 17, 20, 25 right now are going to use what’s available to make beautiful, hilarious fun things.”
Bad things can happen, he said. But if you hold on, “you start to see the landscape around you change and you see opportunities.”
“There’s no better person I could be sharing the stage with right now than you,” O’Brien told Colbert.
In true Conan O’Brien style (go check out his delightfully over-the-top appearance on “Hot Ones”), the interview presented a prime opportunity for him to break the form. He resisted Colbert’s composed line of questioning, criticizing his sedate delivery of biographical information. “This is like a trial deposition,” he said at one point.
“Do you even like me?” he asked at the top of the event before flinging an “awful” pillow from his chair onto the stage.
“When did this become ‘Judgement at Nuremberg’?” he asked when questions from the crowd got a little critical of him, which fit nicely with his penchant for self-deprecation and comedic self-aggrandizement.
When several people left their seats and headed for the door just as the audience Q&A portion began, O’Brien called them out.
In another part of the night’s proceedings, O’Brien said it all seemed like a play, so he and Colbert got up and started ad-libbing dialogue.
Growing up, O’Brien, the third of six children, was driven by his parents and family sitting around the table and laughing at his “chicanery.” “I had a burning desire to be someone,” he said, so he decided to be a good student, working his way to Harvard. He swiftly rose through the ranks at The Harvard Lampoon, becoming the humor magazine’s president as an underclassman.
In 1984, he had the chance to spend time with John Candy, who was visiting the campus because The Lampoon gave awards to comedians. They included Bill Cosby, whom O’Brien picked up in his dad’s station wagon. (O’Brien neglected to clean the back seat and Cosby found a Big Mac wrapper.)
Candy, he said, “was everything I wanted him to be. He was Falstaff.”
O’Brien, a big fan of the actor-comedian’s work on “SCTV,” accompanied him around town as he picked out eclairs at a bakery in defiance of his diet. “They’re Pritikin eclairs!” he told O’Brien.
O’Brien was supposed to drive Candy to his show on campus in a limo, but Candy decided to hang out with friends and meet him there. “I’ve lost John Candy,” O’Brien said, recalling his panic.
He nervously vamped for the college crowd for 20 minutes, bombing as everyone waited for Candy.
Later, O’Brien told Candy that he planned to try comedy. The comedian, who had been a “funny imp” all day, looked at him and got serious for a moment. “You don’t try comedy,” he said.
“And I knew what he meant,” O’Brien said. “(You) burn the ships on shore so you can’t look back. You have to go all in. A chill went up my spine when he said it. And I never forgot that.”
NEIL GRABOWSKY
Stephen Colbert and Conan O’Brien at NJPAC.
Candy died in 1994, when O’Brien was in his first year hosting “Late Night.” “My dream was to finish the circle and have him on the show,” he said.
He never got the chance.
These days, Conan fans can immerse themselves in hours of interviews and material via the “Conan O’Brien Needs a Friend” podcast, co-hosted since 2018 by O’Brien’s former assistant, Sona Movsesian, and producer Matt Gourley.
“I started it as kind of a joke,” O’Brien said.
One of the draws of the podcast was getting to read ads as his wacky self. Plus he got to include Movsesian. “She is the most remarkable person because it’s been scientifically proven that when you observe an object, it changes. Most people, when you put a camera on them, they change in some way,” he said.
With Movsesian, the crowd size or audience doesn’t matter. “Sona doesn’t change,” O’Brien said. “She does her thing and she walks offstage and says, ‘I want a sandwich.’ ”
When Colbert walks offstage for the last time at “The Late Show” next year, O’Brien has no doubt it won’t be long before he resurfaces.
“The world is your fucking oyster,” he told Colbert. “It’s gonna be amazing.”
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