Conan O’Brien has proved to be the king of awards shows.
O’Brien has hosted many award ceremonies through the years, including the 2025 Academy Awards.
“There’s a lot of different parts of [preparing for the Oscars], and you start thinking about different bits and what could [you] do for pre-tapes [or] what kind of production number can we have,” he said on a March 2026 episode of Michelle Obama’s “IMO” podcast. “You’re always thinking about jokes. ‘What could the jokes be?’ You really want to test them, and one of the ways to do that is to go out to clubs.”
According to O’Brien, he tried to make the audiences “part of” his testing process during his impromptu comedy club sets.
“You say, ‘Look, if you guys laugh at a joke that isn’t good, that might convince me to do it and then I’m going to die on the Oscars, so please don’t do that to me,’” he said. “They’re laughing at the part where you’re not even reading the joke. I love that.”
Luckily, the jokes that O’Brien did tell landed and he was asked to host the 2026 Oscars.
Keep scrolling to revisit O’Brien’s best award show moments through the years:
March 2025
While hosting the Oscars in 2025, Conan O’Brien couldn’t resist trolling nominee Timothée Chalamet.
“Timmy Chalamet is up for Best Actor tonight, you’re amazing and you look amazing. I love that suit,” he said of Chalamet’s yellow tuxedo. “You will not get hit on your bike tonight.”
Chalamet made waves earlier that year when he took a rideshare bike to the London premiere of his movie A Complete Unknown, for which he was slapped with a fine.
O’Brien kept poking fun at Chalamet, joking about his portrayal of Bob Dylan, his youth and the confusing premise of Dune 2.
“It’s fine, we’ll hang after this,” O’Brien added, attempting to smooth any bad blood over to no avail. “That was a no.”
March 2025
Conan O’Brien’s debut Oscars hosting gig wasn’t all about jokes, as he seriously addressed the devastating wildfires that affected Los Angeles earlier in 2025.
“The people of Los Angeles have clearly been through a devastating ordeal and this needs to be addressed,” he somberly said at the top of the show. “In moments such as this, any awards show can seem self-indulgent and superfluous, but what I want to have us do is remember why we gathered here tonight.”
He continued, “Even in the face of terrible wildfires and divisive politics, the work, which this is about, the work continues. And next year, and for years to come, through trauma and joy, this seemingly absurd ritual is going to be here … the magic, the madness, the grandeur and joy of film worldwide is going to be with us forever.”
September 2006
Conan O’Brien kicked off the 2006 Emmy Awards with a visit to Dunder Mifflin, a.k.a. the site of The Office. In a pre-taped sketch, O’Brien climbed from the ceiling into the paper company’s office where the entire cast had been working.
“No, I did not have Conan O’Brien fall through the ceiling,” John Krasinski’s Jim told the camera.
While O’Brien asked for directions to the Emmys, Steve Carrell’s Michael needed to make sure he “practiced” in advance. O’Brien, however, was too distracted by Pam (Jenna Fischer).
“Pam is very attractive, no question,” he said in a confessional. “I mean, if I didn’t have an award show to host, I could easily see having two to three seasons of will-they-won’t-they sexual tension that ultimately goes nowhere.”
September 2006
When Conan O’Brien hosted the Emmy Awards in 2006, he had a clever idea to keep the show running on time.
“I have placed beloved TV icon Bob Newhart in an airtight container with exactly three hours worth of air,” he said in his monologue. “Yes, ladies and gentlemen, it’s very simple. If the Emmys run even one second over three hours, Bob Newhart dies, so keep those speeches short. Ladies and gentlemen, Mr. Newhart’s life is in your hands.”
Newhart actually died nearly two decades later in 2024.
September 2006
During Conan O’Brien’s hosting gig at the Emmys, he lamented about NBC’s programming decline by parodying “Trouble” from The Music Man.
“Well, we got trouble, my friends, yes we got trouble right here at NBC with a capital ’T’ and that rhymes with ‘G’ as in ‘Gee, we’re screwed,’” he sang. “I know you don’t care but our network share is just one dude. Well, a few years ago, we were sitting on top with Seinfeld [and] Friends, then those shows bailed and the new ones failed, and it started a trend.”
September 2002
Conan O’Brien hosted the Emmy Awards in 2002, where he opened the show with a pre-taped sketch featuring Ozzy Osbourne, Sharon Osbourne and their family.
“What the hell happened? You’re supposed to wake me up,” O’Brien asked Ozzy, who died in 2025, about the reason he overslept for the ceremony. “I’m hosting the Emmys.”
Ozzy yelled back, “I didn’t f***ing know, man. I’m not your f***ing keeper. You’re in my f***ing house.”
Sharon, meanwhile, tried to fix the situation, asking where O’Brien’s suit was. The emerald-colored tux, however, had been ripped up by the family dogs.
Later, O’Brien knocked on the bathroom door, where a teenaged Jack Osbourne was “burning something” inside the sink. Jack’s sister Kelly Osbourne subsequently helped O’Brien apply makeup, leading to another argument.
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