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.

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.

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.

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

Adam Sandler doesn't really care what you think. In a 2024 interview, the actor was asked about his utterly singular personal style, which he distilled thusly: “Whatever's in the closet, I grab it. I don't think about it much. Most people make fun of me, but I keep moving.”

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.