The host left late night in a sincere, meandering, clip-heavy finale.

Conan O'Brien never looked comfortable. After 28 years, he was the grand old man of late night. But late night now exists as raw material for morning virals, and grand old men get disgraced every day. So O'Brien's manic sizzle was a clever defensive maneuver. The last few decades were centuries of techno-cultural evolution. Moving too slow meant stopping — and wasn't his documentary called Conan O'Brien Can't Stop?

"When I started there were three late night hosts," he said on Monday night's Conan. "Now there's 25 hosts, and I'm the 'I Thought You Died Six Years Ago Guy.'"

Too harsh, and that number is way too low. There are indeed a few dozen people hosting nominally late night-ish programs on various platforms you could hazily define as "television." But anyone with vaguely humorous online persona shares a lineage with O'Brien. Just take a look at this amazing list of essential Conan sketches. Faux headlines, a cuddly creature being grossly sexual, extremely in-depth Star Wars humor: It's a roadmap for a whole epoch of humor, The Onion and Avenue Q and all the great works of literature that will never achieve the massive attention afforded that damn Attack of the Clones meme.

Conan says farewell
Conan O'Brien says farewell to his TBS late-night show.
| Credit: TBS

O'Brien and his collaborators didn't create that entire style of comedy. But in the early years, they were perfecting their deadpan-absurdist approach in real time, after midnight, five nights a week. Toward the conclusion of Thursday's Conan series finale, O'Brien himself described his focus as "this strange phantom intersection between smart and stupid." Bill Hader, the guest on Monday, spoke with generational longing about those early Late Night episodes.

"It was the first thing in comedy that was mine," he said. "It was the first thing in comedy that my parents didn't understand."

Just a few years later, cable networks were building followings off out-there comic weirdness. But Late Night was vanguarding all that on broadcast television, mere minutes away from limp Jay Leno schtick. So O'Brien was the first late night host I ever loved, and Conan's series finale on TBS should feel momentous.

But this last week of shows made for an awkward event. It was less a goodbye than an extended "Seeya Tomorrow." O'Brien talked about his plans to "re-emerge on HBO Max at some point," and TBS will continue his acclaimed Conan Without Borders specials. A blank mandate for a variety show plus paid world travel equals one swell non-retirement plan. He's got a podcast, and he's got a companion podcast. A sketch earlier in the week warned O'Brien of potential dark futures: hosting a game show, shilling for car dealerships, doing anything on reality TV. The jokes felt a bit limp because that's so obviously not the oncoming trajectory. He's a valued WarnerMedia property, on the billboard next to Batman and Friends.

Will Ferrell came closer to the mark in his Zoom appearance on Thursday. It was the third time Ferrell came on a series finale for a Conan O'Brien show, and he banked a few more farewells for imaginary projects: A short-lived HBO Max series, a Delta In-Flight Talk Show, a YouTube channel for unboxing. Funny to imagine that desperate flailing, though it's more timely to worry about what a streaming berth can do to a once-brilliant creative mind. O'Brien's hero David Letterman looks like he's having fun at his Netflix celebrity praise summits, so that makes one of us."I will always be on television for all eternity!" O'Brien joked. Literally, though.

To clarify: Even if he didn't look it, O'Brien certainly felt comfortable at some point. No man wears a denim jacket without believing in himself a little too much. These final shows had a leisurely nothing-to-prove quality, old friends onstage chatting through one actual marijuana haze. On Wednesday, Dana Carvey strolled in wearing your dad's roomiest track jacket and consulted some nominally handwritten notes for new material.

"This is my second-to-last show," O'Brien yelled incredulously, "And you're trying s--- out on a piece of paper!?!?!"

The vibe was very much "filmed podcast," which is how a lot of expensive content nodes feel lately. (O'Brien kept telling the TV audience to check online for the uncut episodes.)

Thursday's finale stretched past an hour to accommodate a few clip reels and a more-cute-than-funny cameo by Homer Simpson. O'Brien wrapped the night by thanking everyone he possibly could. This was an obviously sincere act of cosmic gratitude, and only a monster could protest. (It did sound like one of those laundry-list Oscar speeches where the winner winds up thanking their agent's second assistant.) Oddly, the most classically O'Brien-ish moment of the finale was medically unplanned. Climactic guest Jack Black walked onstage with a cane, having sprained his ankle rehearsing an elaborate musical number. It was hilarious watching Black and O'Brien try to explain this confusing series of events, partially because you couldn't tell if the explanation was itself an elaborate bit. Black still stood up to belt out a Conan-ified version of "My Way," a musical triumph over bodily injury only a monster could protest. (It was fine.)

"No one in the last 30 years," Carvey had told O'Brien, "has done this much comedy that's this good." It's a boldly unprovable compliment from one close friend to another — they have the same therapist! — and the craziest thing is I sort of believe it. O'Brien at his late-night peak was a sight to behold. Long-timers probably recall his throw-it-at-the-wall '90s heyday. For me, the mid-2000s were the golden age, even without the amazing sidekickery of Andy Richter (who spent that decade pursuing a brilliant-yet-cancelled sitcom career.) In 2004, NBC promised O'Brien he'd get The Tonight Show in 2009. For five years — before the Betrayal — Late Night was what the future looked like. You tuned in to watch the inmates in the playground preparing to seize the asylum.

By my rough calculations, O'Brien spent around 2 percent of his late-night career hosting The Tonight Show. 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.

Nobody in late night wants to fight anymore, of course, which is one reason we move closer every day to utopia. But that tumultuous period made for mesmerizing television. O'Brien's last Tonight Show felt like the end of an era, not least because it was funny as hell. I rewatch that episode of television frequently, and that is obviously unfair to Conan, which ran for 11 congenial years. Is it unfair to O'Brien, too? That was not an easy time for him, to put it mildly.

On Thursday's finale, O'Brien vaguely referenced how absolutely no one in 2010 understood why he chose to take his talents to TBS. The host recalled Turner Entertainment president Steve Koonin giving him a promise: "I will protect you, I will let you and your people do what you want, I will never interfere."

That must have sounded like paradise after what happened at NBC — and practically the last words O'Brien said on Thursday were "Heaven on earth." Conan didn't end with any kind of bang, but it ended on O'Brien's terms. Eternity awaits.

Hear more on all of this weekend's must-see picks, plus what Bosch star Titus Welliver is watching, in EW's What to Watch podcast, hosted by Gerrad Hall.

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