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.

In a rare crossover between the Golden Globes & the Oscars, Adam Sandler was part of both ceremonies' opening monologues for a Timothée Chalamet joke.

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’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.

The internet is still buzzing about Adam Sandler’s bizarre Oscars outfit on Sunday, March 2. While stars like Colman Domingo and Cynthia Erivo opted for designer’s tailored and stunning ensembles for the 97th annual Academy Awards,