As Conan O’Brien kicked off his opening monologue at the 97th Academy Awards, he couldn’t resist repeatedly trolling nominee Timothée Chalamet.
“Timmy Chalamet is up for Best Actor tonight, you’re amazing and you look amazing. I love that suit. You will not get hit on your bike tonight,” O’Brien, 61, said during the Sunday, March 2, during the awards ceremony held at Los Angeles’ Dolby Theatre, referring to the actor receiving a fine for taking a rideshare bike to the London premiere of A Complete Unknown. “Safe! Amazing actor. Timothée is nominated for his portrayal of Bob Dylan, yeah. Bob Dylan wanted to be here tonight, but not that badly.”
O’Brien went on to note that Chalamet, 29, also appeared in the Dune sequel, which is up for Best Director (and several other trophies) during Sunday’s show. “Guess what? I’m told [Denis Villeneuve] banned smartphones on the set of Dune 2. Apparently, his actors kept Googling, ‘What is this movie about?’”
O’Brien did try to settle any bad blood with Chalamet, who sat in the front row with girlfriend Kylie Jenner.
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“It’s fine, we’ll hang after this,” O’Brien quipped. “That was a no.”
Later in O’Brien’s monologue, he tried to humble all of the nominees by sharing their first-ever acting headshots.
“And it means you, Timothée Chalamet,” O’Brien added before showing a sonogram picture, joking about Chalamet’s youth. “I did that to them, and so, it’s only fair to do it to myself.”
The monologue, which ended with a surprise musical number, also featured a cameo from a casually dressed Adam Sandler.
“Adam, what are you wearing?” O’Brien asked, referring to Sandler’s signature hoodie and sweatpants. “You’re dressed like a guy playing video game poker at 2 a.m., Adam.”
Sandler, meanwhile, stressed that he “liked the way” he dressed because he’s a “good person.”
Before Sandler left the Dolby Theatre over O’Brien’s mocking, he shouted, “One more thing — Chalamet!” and ran over to greet Chalamet with a hug. (Sandler, 58, jokingly mispronounced Chalamet’s last name during the Golden Globes in January.)
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Sunday is O’Brien’s first time emceeing the Oscars.
“We are thrilled and honored to have the incomparable Conan O’Brien host the Oscars this year,” Academy CEO Bill Kramer and Academy President Janet Yang said in a November 2024 press release. “He is the perfect person to help lead our global celebration of film with his brilliant humor, his love of movies, and his live TV expertise.”
The statement concluded, “His remarkable ability to connect with audiences will bring viewers together to do what the Oscars do best — honor the spectacular films and filmmakers of this year.”
O’Brien, an Emmy-winning late-night host, previously teased how he was preparing to emcee the awards show.
“We’re gonna have a great show [and] a great show,” O’Brien said on the Wednesday, February 26, episode of Jimmy Kimmel Live! before joking, “Things for me, you know, come together very late. I started working on the Oscars about four hours ago. I’m gonna pull an all-nighter. I think we have some fun ideas or some great surprises.”
According to O’Brien, he “owed” Kimmel, 57, gratitude for his advice. (Kimmel hosted the Oscars broadcast in 2017, 2018, 2023 and 2024.)
“One of the first calls I got after agreeing to host the Oscars was from Jimmy Kimmel,” O’Brien said earlier this month. “I didn’t pick up because I have caller ID, but then I thought about it and I called you back.”
Kimmel subsequently invited O’Brien to meet up to trade Oscars wisdom.
“You and Molly [McNearney, Kimmel’s wife] could not have been more gracious,” O’Brien gushed. “They gave me all these great tips.”
As part of O’Brien’s prep, he made sure to “watch a lot of movies” that scored nominations after coming to the realization of why he wanted to host the Oscars in the first place.
“I wrapped up my late-night show a couple years ago,” he recalled. “It was a dream … and when it ended I was done. I thought, ‘Now, I want to just try things that scare me. If it scares me, I think I should do it.’”
