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’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.