Back in 2014, when Chalamet was still looking for his big break in Hollywood, he scored his first-ever film role in Jason Reitman’s Men, Women & Children, a comedy-drama that also starred—you guessed it!—Adam Sandler. While a lot has changed for Chalamet since then (say, 24 movies and two Oscar nominations), the pair remain friendly to this day.

Adam Sandler doesn't do dress codes. The 58-year-old comedian showed up to the 2025 Oscars on Sunday, March 2 in baggy basketball shorts, sneakers, and a baby blue zip-up hoodie — standing out in a sea of tuxedos at the Dolby Theatre in Los Angeles.

Adam Sandler, wearing shorts and a sweatshirt, ran up and hugged Timotheé Chalamet at the Oscars and acted, well, like Adam Sandler. See what he said

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 may not be nominated at this year’s Oscars, but that didn’t stop the actor and comedian from crashing Conan O’Brien’s opening monologue at the top of the ceremony. Sandler was roasted by the host for dressing so casually at Hollywood’s biggest night. “Adam, what are you wearing?” O’Brien asked Sandler from the stage. …

"Nobody even thought about what I was wearing until you brought it up," the comedian accused host Conan O'Brien Adam Sandler is crashing the biggest party in Hollywood! The actor, 58, made a surprise appearance at the 97th Academy Awards on Sunday ...

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!'

In a rather bizarre interaction at last night's Oscars, Timothée Chalamet is reported to have given Adam Sandler an odd nickname shortly before the Happy Gilmore star stormed out of the event. Last night (2 February) saw the Dolby Theater host the 97th Academy Awards as Hollywood's elite celebrated the last 12 months in film.

One X user called Adam Sandler's exchange with Conan O'Brien the “best bit in the last 20 years of the stuffy Oscars.”

Nikki Glaser is sharing her thoughts on Adam Sandler continuing her Timothée Chalamet joke at the 2025 Oscars: 'I saw like a callback.'

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.