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 went full Billy Madison during a bit at the 2025 Academy Awards on Sunday night.During his opening monologue, Oscars host Conan O’Brien took it upon himself to act as fashion police and told the celebrity-studded crowd that it was of utmost importance “that everyone is properly dressed” for the event.

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.

Adam Sandler crashed Conan O'Brien's opening Oscars monologue and got roasted for dressing casually, before yelling at Timothée Chalamet on his way out.

The 97th Academy Awards, also known as the Oscars, took place on Sunday at the Dolby Theatre in Los Angeles. Conan O’Brien hosted the ceremony, honoring the best in cinema from the past year. Notable presenters included Halle Berry, Penélope Cruz, Scarlett Johansson, Oprah Winfrey, Cillian Murphy, Emma Stone and more.

The 'Happy Gilmore' actor is notorious for his laid-back style — and Timothée Chalamet got in on the bit, too.

Adam Sandler’s signature effortless outfit–an oversized hoodie paired with basketball shorts–has cemented him as an unlikely Gen Z style trendsetter. His laid-back “Adam Sandler chic” aesthetic has gone viral on TikTok–so much so that he was the subject of a surprise bit with Conan O’Brien at the 2025 Oscars that led to him playfully leaving the Dolby Theater.

A-list actor and comedian Adam Sandler has developed quite a reputation for his rather unique fashion sense – or lack thereof. During the Oscars on Sunday night, host Conan O'Brien couldn't help but poke a little fun at him for it.