Conan O’Brien Just Can’t Help Himself

Conan O’Brien made me promise not to repeat the joke. Should it survive long enough to make the cut for his Oscars monologuehe understandably doesn’t want the punchline spoiled. “It’s like this little baby bird that I’m cradling,” he sayscupping empty palms as if they could protect the words from his own merciless edits.

We’re backstage at Largothe Los Angeles comedy cluband O’Brien just delivered 20 minutes of the material he’s been honing for three months. The surprise set is one of several he’ll make as he workshops his way through the Southland in approach of his March 15 engagement hosting the Academy Awards. Each performance follows a day largely spent in the writers room. If he biffs it on the big nightit will not be for a lack of preparation.

Joined by five of his writerstwo of whom were planted in the audienceO’Brien and company debate what landed the way they thought it mightwhat could play better with the industry crowd inside the Dolby Theatre versus the TV audience andat least as I imagine it after I’ve left themwhat surgical adjustments will be made before the next trial run. “I get obsessive,” says O’Brien. “I want to turn it offbut I can’t. That’s not always a fun ridebut that’s the deal. At 62I understand it. I tell my daughter‘You have to know your own owner’s manual.’ I now know the Conan Owner’s Manual.”

O’Brien’s first go at the Oscarsin 2025was quite well-received. He signed on for his encore two weeks later. “I don’t watch a lot of those thingsbut I just remember thinking‘Is this the greatest Oscars ever?'” says John Mulaney. “Conan is a true artist and an incredible broadcaster. He’s also got one thing that you cannot fake and can only earnwhich is stature.”

Any live telecast is a flirtation with disaster. Electing to run this particular gauntlet could justifiably be interpreted as masochism — especially for O’Brien. In a career where he was so often positioned as the underdogthere is little doubt that he’s summiting the height of his powers. Retiring in 2021 from late nighta sector of media currently in dramatic free fallhe now looks like a prophet. He’s got a wildly successful podcastone that landed him a $150 million deal at SiriusXMand an Emmy-winning travel show. He’s taking opportunities he never had beforeand playing very against typeappearing opposite Rose Byrne in Mary Bronstein’s harrowing dramedy If I Had Legs I’d Kick You. He has the respect of his peers; a wifeLizahe speaks of with such admiration; and two children who’ve grown into young adults he proudly describes as good people. And while he sometimes might wish for a smaller profile — in DecemberO’Brien’s name was tacked onto horrific headlines when friends Rob and Michele Reiner were murdered the morning after attending his holiday party — he seems truly content with how his life and career have shaken out.

So why the hell is he tempting fate by taking the most thankless gig in Hollywood? Again?

“When the first offer came inI told him‘You don’t need to do thisyou’ve got nothing to prove,’ ” says Jeff RossO’Brien’s close friend and executive producer through all three iterations of his tenure as a talk show host. “When we quit late nightthe goal was to only do things that are funthings that we want to do. Wellthis is what Conan wants to do.”

His HBO Max travelogueConan O’Brien Must Gois aptly titled. O’Brien claims to have little control over these choicesat least where his career is concerned. “There’s a little bearded Viking inside me,” says O’Brien. “He’s been there since I was 10 years old. And when that Viking decides on something — whether it’s replacing David Letterman with no experienceskiing some advanced slope I have no business going down or hosting the Oscarsthat’s what’s going to happen.”

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This Viking apparently does not consider how its decisions impact O’Brien’s mental health. His onscreen penchant for self-flagellation is more than a bit. He agonizes over a lothis material most of all. Despite filming 4,380 episodes of late night TV — first with Late Night andbrieflyThe Tonight Showboth at NBCbefore finishing with a decade of TBS’ Conan — he greets each opportunity to speak in public with fresh enthusiasm and a fair amount of dread.

We’re talking at Team Coco’s Hancock Park headquarters during a break from the Oscar war room. In between pulls of an Erewhon Strawberry Glaze Skin Smoothiethe beverage previously named after Hailey Bieberhe explains how hard he toils over every performance. The only thing harder on him is not having the time to toillike when he recently arrived at a friend’s birthday party to news that there would be speeches and his was the closer.

“I started to go into a bit of a panic,” says O’Brien. “This isn’t televised. No one’s recording it. There’s a bunch of people in the room I don’t even know. So what’s the fucking problem?”

He retreated into his headthinking about what to sayediting and amending his unscheduled set in real time as he heard the other remarks. Once he was on deckhe stole away to the back of the room and stretched his cartoonishly tall frame to psych himself up before taking the stage. He says he did a good job. He probably killed. O’Brien does not recall what he came up with — the memory of most bitshe saysleaves him almost as soon as they materialize — but he can vividly summon what happened next: “I sat downand this older woman across the table looks at me and says‘That took a lot out of you.’ “

At firsthe took offense. “Excuse me?” he asked. “Then she goes‘I was watching what you put yourself throughand it takes a lot out of you.’ It meant so much to me that she noticed. There’s this illusion that comics just get up and do these things.”

Such acknowledgements seem to mean a great deal to O’Brienat least in part because they eluded him earlier in his career. Writing jobs on Saturday Night Live and The Simpsons were executed in obscurity. He describes initial reviews of Late Nightthe job he took over from Letterman when he was still a virtual unknownas universally negative. Even after things were up and runninghe says his idea of funny was never the same as his bosses’ at NBC. What he did not realize for more than a decade was that a legionsome of whom would grow up to be the most influential comedians and actors of todaywere watching with rapt devotion.

At 13Mulaney staged a jailbreak from a sleepover because his friends didn’t want to watch Late Night. It was 1996a Fridayand a promo had teased resolution to the weeks-long bit about O’Brien’s efforts to track down Sanford and Son actor Whitman Mayo. Mulaneyjust before midnightsprinted down Chicago’s Burling Street and made it home in time to watch aerial footage of Mayo arrive by limousine at 30 Rockefeller Plaza and walk onto Studio 6A.

TodayMulaney is part of O’Brien’s extended social circle. It’s a status he speaks about with a bit of wonder. “Simon Rich and I went to Conan’s for dinner onceand we couldn’t believe it was just the two of us there,” says Mulaney. “Conan built a fire. I think the flue was closedbecause the room fills with smoke and he’s trying to open a window and it becomes clear to us that he doesn’t know how his house works. We’re just sitting there like that meme of the dog in the house on fireso happy to be in his presence. Liza came down and said‘Why don’t you guys go in another room?’ I thought to myself‘I’m never getting out of this chair. I’ll happily run out of oxygen.’ “

Mulaney was among the O’Brien disciples and contemporaries to grace the Kennedy Center when he received the Mark Twain Prize for American Humor in 2025back when that venue and honor still existed. For two hoursthe man who can barely utter three sentences without saying something horrible about himself watched the comedy elite wax in adoration and play clips of his career.

“I was dreading that nightbut I loved it,” says O’Brienwho sat in the box tier flanked by Lizahis daughterNeveand his sonBeckett. “I loved it because there wasn’t a person on that stage who didn’t mean a lot to me. Andyeahthey said sweet thingsbut there was a lot of really funny stuff in there. I was laughing the whole night.”

The people around O’Brien pursue his laughs like they’re white truffles. Among the quickest ways to get one is to pitch a stinker. Mike Sweeney was his head writer for years. He directs Conan O’Brien Must Go. And he’s returned as an Oscar writer. If anybody knows O’Brien’s tell when an idea tanksit’s him.

“His tell?” Sweeney repeatslaughing. “His tell is that he mocks it mercilessly for at least five minutes. He’s most delighted in rehearsal when things go wrong or they’re just bad. It’s like delivering fresh meat to the lion’s cage. And if it’s your bit that’s getting evisceratedyou’re laughing as hard as anyone.”

This descriptionas Sweeney predictspleases O’Brien. “Some artists work in oilsome work in clay,” he says. “I am a Picasso at wild passive aggression.”

On paperthis could paint O’Brien as a bit of a dick. So very many comics are. But O’Brien has never found comedy (or pleasure) in being mean. Plenty of people on his staff have stuck with him for more than 20 or even 30 yearsand many speak about him with as much protectiveness as they do reverence.

Sona Movsesian started working for O’Brien in 2009first as his personal assistant. Now the co-host of his podcastConan O’Brien Needs a Friendshe is best known for endlessly roasting him. “Once you make fun of your boss and he doesn’t fire youit gives you license to make a thousand jokes about your bossand now that’s my livelihood,” says Movsesian. “But I’d be here either way. If you start working for Conanthat’s your job for the rest of your life. If you’re lucky.”

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The last time I was in O’Brien’s office was early 2024. He was about to record Hot Onesthe Sean Evans-hosted YouTube show where celebrities subject themselves to interviews while eating increasingly spicy chickenand I remember him giddily describing his plan to bring along writer José Arroyo to pretend to be a doctor and check his vitals. We discussed late night TV’s steady declineand he was not bullish on that front. But he wasn’t quite ready to wave the white flag. Thenin AprilHot Ones dropped.

Twenty-seven minutes of O’Brien going absolutely feral as the wings got spicier and spiciermore pop performance art than comedyhijacked the news cycle. His name was so inescapable on social media that some friends initially worried he’d died. The episode has since logged more than 15 million views on YouTube alone.

“That was the moment the scales fell from my eyes,” he says. “If a guy can do World Series numbers with overhead that lookedto meto be about $600and you have every big star lining up to do his show or Chicken Shop Date … that’s when I profoundly understood that late night shows are in trouble.”

“Trouble” is generous. CBS announced its full retreat in Julycanceling The Late Show With Stephen Colbert in what it called “purely a financial decision.” But most observers linked the decision to Colbert’s criticism of Donald Trump and CBS owner Paramount’s desire to move along regulatory approvals for its sale to David Ellison’s Skydance Media. In SeptemberDisney pulled Jimmy Kimmel Live! from the air when the host’s muddled comment about slain MAGA provocateur Charlie Kirk drew the ire of Trump’s FCC. Industry outcry was immediate. Kimmel was back on air a week laterbut fears about government interference and free speech linger. Hollywood consolidation only compounds these anxieties.

“I’m of the mind that yesthese shows are going away and will become something else,” says O’Brienwhose own material has never been overtly political. “But I don’t like when other malign forces intervenebecause they’re trying to curry favor. That pisses me off.”

For the better part of the past yearO’Brien has tried to be an optimistic voice for Colbert. “Conan is the patron saint of ex-talk show hosts,” says Colbertwho watched with curiosityalongside his shrinking fraternityas O’Brien remade his career. “He’d actually been telling me to quit for years. We were outa few Emmys agoand he kept saying‘I want you to know there’s a lot of fun to be had when this is overso don’t feel like you need to stay.’ It almost hurt my feelingsbut he was just being kind. He Dutch uncle’d me.”

O’Brien’s words likely hold more water with Colbert because he once saw his own employment drama make international news. NBC’s botched Tonight Show successionduring the 2009-10 seasonended in the network returning the time slot to Jay Leno and O’Brien walking away from his dream job. As soon as his media gag order expiredhe broke his silence on 60 Minutes. He’d wrapped a successful stand-up tour. He was about to launch his cable show. The public was on O’Brien’s sideand there was the not-insignificant $30 million payout from NBC. It was meant to be a victory lap. But the interview footage shows O’Brien as staid and forlorn as you’re likely to ever see him.

“It’s that Catholic thingwhere you never want to admit that something’s painful,” O’Brien says. “I went so far in the other direction and acted like it was the best thing that ever happened to me. And I did get to do all of this great stuffbut it’s clear to me now that I was profoundly depressed and angry for a couple of years. I made the mistake of trying to bypass that part. I thought I was fooling myselfand I now see that I wasn’t fooling anybody.”

O’Brien may have been burned by late nightbut he also devoted most of his career to it. Like any good Boston boyhe finds an anecdote about the Red Sox to articulate his complicated feelings about its inevitable demise.

“Ted Williams is a god in Boston,” O’Brien says of the Splendid Splinter“and right before he diedthey wheeled him out at Fenway Park. There’d been this rumor that they might build a new stadiumso somebody puts a microphone in his face and says‘Mr. Williamsthey may build a new park. How do you feel about that?’ Everyone is expecting him to say‘My Godthis can’t happen to this green temple to baseball.’ Insteadhe says‘Tear it down.’ ”

“I try not to get sentimental about change,” he adds. “There are no good old days. There is only change.”

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A strong rationale for asking O’Brien to host the Oscars is thatlike Kimmelhe’s of a rare class that can put an intimidating room like that at ease. His Hollywood friends and acquaintances are manyas evidenced by his annual holiday party attended by the likes of Tom HanksJane FondaAdam Sandler and Martin Short. Jason Bateman once openly campaigned for an invite on his SmartLess podcast. But this year’s party was plastered all over the news when friends of the O’BriensRob and Michele Reinerwere found murdered in their home the next day. Their son Nickwho attended the party with his parentsis charged with their murder and awaiting trial. On Feb. 23he pled not guilty. It is a nightmare scenario for any familyone compounded by the Reiners’ countless close relationships and reputations for good works.

Their loss is something O’Brien chose not to address on his podcasttelling me that the idea of bringing it up in his own forum felt disrespectful. When he was finally asked about the Reiners during a February recording of The New Yorker Radio Hourhe said that he’d been in shock for some time. He did not talk about the fact that he essentially became a cultural bystander in the media firestorm that followed. When I ask him how he and his wife have processed their association with something so brutala question he expectedhe summons an answer he’s obviously given great thought to.

“Very simplywe had a partywe invited our really good friends and thenthe next daythis terrible thing happened,” says O’Brien. “Whatever difficulties my wife and I have experienced having our name attached to it are nothing compared to the scale of the tragedy for the family and the loss of Rob and Michele. If you’re a known personyour name is going to get dragged into things sometimesbut it is not a hardship. There is only sadness that they’re gone.”

O’Brien openly worries he’s reached the point in life where loss is now a constant. In December 2024Thomas O’Brien95and Ruth O’Brien92died three days apart on the eve of what would prove to be one of the most monumental years of their son’s career. “The beginning of my life in comedy is not The Groundlings or Lorne Michaels,” says O’Brien. “Those are important partsbut the beginningmy nuclear fuelwas seeing that I could make my parents laugh. I used to get a huge dopamine hit from just telling my parents good news. ‘Guess what? We just got picked upI’m not canceled yet,’ or ‘Guess what? I won an Emmy.’ When they diedI did have a moment of‘What now?’ “

For all of the joy he got during his evening at the Kennedy Centerthe thought did cross his mind later that night that perhaps he’d reached the point in his career where he couldas he puts itstep off the boat. “I don’t know what that means,” he says. “I’m not going to go into the woodsget a little kiln and make pots.”

Such musings never last long. O’Brien knows thatinevitablyanother interesting offer will come along and that the Viking will say yes.

This story appears in the March 11 issue of The Hollywood Reporter magazine. Click here to subscribe.