During his monologue, O'Brien singled out his longtime friend for being "dressed like a guy playing video poker at 2 a.m."

Adam Sandler’s fashion sense, or lack of it, gained even more notoriety at the Oscars on Sunday as host Conan O’Brien mocked his casual look in one of the night’s skits.

Adam Sandler cracked up the Oscars crowd during Conan O'Brien's opening monologue, encouraging attendees to join him in a game of basketball after the ceremony and then storming out: 'Chalamet!'

Adam Sandler made an unexpected fashion statement at the 2025 Oscars on Sunday night, and host Conan O'Brien had something to say about it.

Conan O'Brien kicked off the 2025 Oscars with countless jokes about the nominees, a song about not wasting time and then kicked Adam Sandler out of the ceremony for his iconic downplayed outfit.

The Oscar ceremony had its flaws, as usual, but the humor was surprisingly good thanks largely to host Conan O'Brien.

Host Conan O'Brien performs onstage during the 97th Annual Oscars ... [+] at Dolby Theatre on March 02, 2025 in Hollywood, California. Getty Imag

Adam Sandler walked out of the 97th Academy Awards during Conan O’Brien’s opening monologue after the ceremony host took a swipe at this outfit choice. At such a critical moment in US history, we need reporters on the ground. Your donation allows us to keep sending journalists to speak to both sides of the story.

Conan O’Brien couldn’t help but reference the beef that dominated headlines for the past year during his hosting gig at the Academy Awards, mentioning the back-and-forth between Drake and Kendrick Lamar. “We’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile,” he said, taking a …

With a lead-in that included a sentimental tribute to fire-ravaged Los Angeles and then Ariana Grande and Cynthia Erivo performing several showstoppers from Wicked, “four-time Oscar viewer” Conan O’Brien made his Oscar hosting debut tonight with a lot to prove. And what better way than to emerge Substance -like from Demi Moore?

Nikki Glaser shares her thoughts on the Oscars and grading Conan O'Brien's hosting and reveals her favorite moments from Sunday's ceremony.

Adam Sandler is crashing the biggest party in Hollywood! The actor made a surprise appearance at the 97th Academy Awards, where he appeared in a hoodie and basketball shorts in his signature style.