Conan's talents transcend the talk show format, says Dennis Perkins. Yet for the past 28 years, Conan was entrenched in a late-night format that was always an awkward fit. "When O’Brien took over Late Night, the late-night hosting post was a cultural sinecure, a comic throne from which to bestow laughs upon those guests granted an audience," says Perkins. "But Conan is not a removed and beneficent bestower—he’s a once-in-a generation comic jester, whose true place is down in the comedy trenches, leaping at every opportunity to find the joke, no matter where he lands. Jumping metaphors a third time, Conan’s not the ringmaster, he’s the funniest clown in the center ring spotlight, who’s also secretly the brains of the whole outfit." Perkins says it was a good thing that The Tonight Show never worked out for Conan because NBC's 11:30 p.m. timeslot would've dulled his off-the-wall comic originality and sparking weirdness. "The current, Jimmy Fallon-hosted incarnation shows just what it would have looked like if O’Brien had truly succumbed to his Tonight Show fate—a wan, charmless cruise of effortful wackiness and placid fawning," says Perkins. Now that he's free of the talk show format, Conan can go back to being "Conan." "With his upcoming move to whatever the hell he’s going to be doing on HBO Max—we know it will be weekly, in the variety show family, and most likely weird, but that’s about it—O’Brien is finally, after almost three decades, stepping wholly away from a hand-me-down entertainment format that never quite fit him properly, and that he never really needed," says Perkins. "And, unlike Letterman’s more genuine retrenchment into prospector-bearded semi-obscurity (and the occasional comedy emeritus Netflix sit-down), there’s a genuine sense of freedom and joy at the prospect of Conan O’Brien deciding to stay in the game, on his own terms. With a cushy HBO deal supplementing his thriving and hand-tailored multimedia Team Coco comedy empire, the late-night-battle-hardened, 58-year-old Conan is striding into a free-form, subscriber-subsidized playroom where he can get back to letting his legendarily febrile comic imagination do whatever the hell it wants. After 28 years, it’s about time."
Conan O'Brien's self-consciousness is what sets him apart from Jimmy and Jimmy and James and Stephen: "They are all more or less regular guys where he is an irregular one; even his whiteness is a different shade of pale. In classic rock terms, it’s the difference between being a fan of Neil Young and a fan of those other guys in that supergroup," says Robert Lloyd. "He is a performer almost by accident, a writer who suddenly found himself — a man who needed much introduction — in David Letterman’s Late Night chair, shot from a cannon. But that he thinks like a writer must also have influenced the fictional frames his late night shows put around the more or less nonfictional appearances of his guests....His energy and his looks — Short called him a 'a ginger crash-test dummy' — make him hard to place chronologically, O’Brien is 58; he will have been getting AARP mailers for some time now. For late-night-retirement context, he’s eight years younger than Johnny Carson was when he quit The Tonight Show, a decade younger than David Letterman when he left Late Show, a year younger than Jay Leno when Leno turned the keys to The Tonight Show over to him in 2009, before taking them back for another four years. He has stayed in longer than his contemporaries but is getting out sooner than his elders, making sure not to stay too long at the fair. Probably he would have found the measure of The Tonight Show eventually. But perhaps it worked out for the best. O’Brien’s self and sensibilities truly are a little strange, a little disturbing, a little bit out of the way. It’s not that I would wish less success on anyone, but TBS may have been the better fit in the long run. Bigger is not always better; budget is the mother of invention. In the end, it proved only that there is more to late night than a name or a network. If anything, it was a matter of being struck down only to become more powerful: The imbroglio made O’Brien into a cause, Coco of Team Coco; it gave him an underdog’s advantage, set him on the moral high ground and laid the grounds for his future."
Conan’s speech to close out his time in late-night was one of the best ever: "I legitimately feel that it will go down in TV history as one of the best ever," says Andrew Sanford. "It was packed with so much gratitude, so much love. Also, Conan didn’t try to revel in it. He didn’t spend the whole time patting himself on the back, he thanked the people who helped make his journey possible. He showed humility in a way that not many people in his position would be able to. I fully acknowledge that my bias may be showing here. Conan is the first late-night talk show host I ever felt a connection to. But dammit, he stuck this landing like a pro. Television will not be the same without Conan O’Brien. The future of late night is a bright one, but it is changing rapidly. Conan’s exit is further proof of just how big that change is. An era has ended and the landscape is forever different. Raise a glass, give a salute or a toast or a moment of silence for one of the best to ever sit behind a desk and tell jokes. Conan’s time in late-night has ended, but his time making us laugh is far from over."
No disrespect to TBS' Conan, but The Tonight Show offered the best version of Conan O'Brien: "By my rough calculations, O'Brien spent around 2 percent of his late-night career hosting The Tonight Show," says Darren Franich. "So it's some kind of cruelty that I constantly think about how amazing his short stint was. The most conventional wisdom today mitigates the importance of the Late-Night Wars, and not just because everything important in 2010 looks idiotic now. Certainly, the Gen Z straw person who torments my sleepless nights thinks the whole Jay Leno Show kerfuffle was a ridiculous bit of privilege infighting, a few white guys holding on desperately to a network model cusping toward apocalypse. Maybe. I think it was a monumental event, the difference between a bright timeline and the dark one we live in. The specific details are too complicated, and memory promotes the macro-drama. See Conan O'Brien, avatar for the ascension of Generation X, caught between the avatars of two other hosting generations. From the past: A boomer who refuses to leave. From the future: A millennial-baiting smiler peddling clickbait nostalgia. I know, I know, silly to point fingers, obviously Jimmy Fallon was just an innocent bystander who mysteriously reaped all the benefits. From 2021, it looks like a temporal pincer movement, and it ended O'Brien's broadcast days. Whatever. O'Brien's eight Tonight Show months were the only Tonight Show for me."
Conan in Korea showcased a wide breadth of aspects and nuances of Korean culture and stayed true to his trademark blend of bizarre yet entertainingly riveting style: "As a Korean American, O’Brien’s Conan in Korea episode held particular significance to me and my family," says Jenny Lee. "At the dinner table, we would laugh and reminisce about O’Brien’s attempts to learn Korean, getting into a snowball fight with a Buddhist monk and adopting an octopus from a fish market and subsequently naming it Samuel. (O’Brien, while unable to bring Samuel home with him to the United States, was able to find him a home at Coex Aquarium in Seoul.) The fact that O’Brien chose to bring along Korean-born American actor Steven Yeun, with whom O’Brien has built up a longstanding friendship throughout the years, to join him in Korea meant a great deal to me and my family. Yeun, who is well-known for his role as Glenn in The Walking Dead and his Oscar-nominated performance in Minari, has spoken in previous interviews about the big influence his Korean heritage has had on him, not only as an actor but as a person. O’Brien not only acknowledged this, he went a step further and took the time to celebrate, learn about, and explore Yeun’s Korean background, getting to know Yeun as a whole person rather than simply as another actor."