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Conan O’Brien Bids a “Smart and Stupid” Farewell to Conan, and Linear TV - Vanity Fair

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Jack Black, Will Ferrell, and Homer Simpson closed out O’Brien’s TBS run before his deal with HBO Max begins. 

For the first time in nearly 30 years, the late night landscape has a Conan-shaped void. Conan O’Brien ended his current show, Conan, on Thursday night, concluding an 11-year run on TBS. His reign as late night’s favorite redhead began 28 years ago, when he assumed hosting duties for NBC’s Late Night from David Letterman in 1993. Next up, O’Brien will lead a weekly variety series for HBO Max, expected to air in 2022.

“I’ve devoted all of my adult life — all of it — to pursuing this strange, phantom intersection between smart and stupid,” the 58-year-old said in his final show. “And there’s a lot of people who believe the two cannot coexist—but god, I will tell you, it is something that I believe religiously. I think when smart and stupid come together, it’s very difficult. But if you can make it happen, I think it’s the most beautiful thing in the world.”

A trio of comedy giants joined O’Brien and his trusted sidekick, Andy Richter, for Conan’s farewell. The longtime host conducted his exit interview with Homer Simpson in homage to O’Brien’s days writing The Simpsons in the ‘90s. “Wow, a dying breed,” Simpson told an animated O’Brien of his late night series ending. “There’s only like 800 of you left.”

Will Ferrell, who also took part in the final episodes of O’Brien’s Late Night With Conan O’Brien in 2009 and his (brief) run on The Tonight Show in 2010, appeared virtually. “If you don't mind, can I pre-tape a few goodbyes, and you can just use them when your next several shows flame out?” Ferrell quipped before sharing farewell remarks for O’Brien’s “late night show on the Al Jazeera network” and his “Delta in-flight talk show.” (The host will continue his Conan O’Brien Needs a Friend podcast and Conan Without Borders travel specials with TBS.)

O’Brien’s final guest of the evening was Jack Black, who coincidentally sprained his ankle while pre-taping a dance in which he was meant to jokingly injure himself. Instead of the planned musical number, Black sang O’Brien and Richter a version of Frank Sinatra’s “My Way” that was instead titled “Con’s way.”

Across late night, several hosts paid homage to O’Brien as he parted ways with the medium. “Conan is a dear friend and a lovely fella who has been nothing but a strength and a great source of advice for me as I took over a late-night show, and I want to congratulate him on 24 incredible years… and several perfectly fine ones as well,” Stephen Colbert said on The Late Show. “I hope he makes the most of his six days of retirement before starting at HBO.” Meanwhile, Jimmy Kimmel offered “congratulations to Jay Leno on his new time slot at TBS”—a reference to Leno seizing The Tonight Show back from O’Brien in 2010, months after promising to pass the torch. O’Brien’s cable television follow-up act arrived in November 2010, when he launched Conan on TBS.

Finally, O’Brien offered guidance to those who may want to occupy the late night desk in his absence. “So my advice to people watching out there right now — it’s not easy to do. It’s not easy to do,” he explained. “It’s not easy to do, but try — try and do what you love with people you love. And if you can manage that, it’s the definition of heaven on earth. I swear to God, it really is.”

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Conan O’Brien Bids a “Smart and Stupid” Farewell to Conan, and Linear TV - Vanity Fair
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