Conan O’Brien Throws Adam Sandler Out of Oscars Over His Outfit

After Wicked stars Ariana Grande and Cynthia Erivo kicked off the show with an electric performance on Sunday night, the comedian hit the stage at the Dolby Theatre in Hollywood.

And Adam Sandler was the star of O’Brien’s monologue.

O’Brien commented on how well dressed the crowd looked tonight, before Sandler was spotted in his typical casual wear, a blue sweatshirt and bedazzled shorts.

“Adam, what are you wearing?” O’Brien asked Sandler from the stage. “You’re dressed like a guy playing video poker at 2 a.m.”

“Nobody even thought about what I was wearing until you brought it up,” Sandler responded. “I like the way I look. Because I’m a good person. I don’t care about what I wear and what I don’t wear. My snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front my peers!”

The segment then saw Sandler deciding to leave the ceremony, as the audience all shorted “no” in unison. But the comedy legend didn’t leave before giving Timothée Chalamet some love — walking up to the Oscar nominee and yelled, “Chalamet!” into his ear, as only he could.

Sandler also invited everyone in the room to “a game of five-on-five basketball at Veteran Park tonight. Midnight tipoff, the guy from… Nosterafu... He’s on my team.”

O’Brien cracked jokes about several of the Best Picture nominees noting how Wicked‘s audiences were left wondering “where did all the minor characters go to college?”

He then made fun of The Brutalist‘s duration, “I didn’t want it to end… And luckily it didn’t.”

In true O’Brien form, nothing was off limits, including the Karla Sofía Gascón drama.

“Little fact for you, Anora uses the F word 479 times. That’s three more than the record set by Karla Sofia Gascon’s publicist,” he said before the camera pointed to Gascon.

“Karla if you are going to tweet about the Oscars, my name is Jimmy Kimmel,” he said.

O’Brien also noted his disappointed about Nicole Kidman’s film, Babygirl missing out on a nomination, noting how it was about a man who couldn’t give his wife an orgasm.

“Antonio Banderas described it as the most challenging role of his career, should have come to me man, should have come to me,” O’Brien joked.

Like all award shows, the host likes to poke fun at how long speeches could potentially go, reminding nominees about the length of award shows.

“If your speech goes too long we’ll cut to John Lithgow looking not angry but slightly disappointed,” he said as the camera pointed to Lithgow.

“And if you still wont get off the stage, I’m going to play hardball, I’m going to show one of your old headshots,” O’Brien threatened before showing Chalamet in the womb as a baby.

The monologue didn’t just end there though, the former late night show also sang a song about not wasting time during the show, where “for no good reason” the Sandworm from Dune 2 appeared playing Chopsticks on the piano.

And while the late-night host didn’t poke fun at Blake Lively’s nasty legal battle with her It Ends With Us costar Justin Baldoni, a dancing Deadpool did appear on the stage.

The 2025 Oscars marks O’Brien’s first time hosting the awards show. O’Brien’s gig came after Jimmy Kimmel hosted the two previous years.