At this year’s Oscars, Adam Sandler showed up with a look that said, “I’m here, but my mind’s still on the couch with a bag of Cheetos.” Known for his laid-back style (and classic movies like Billy Madison), Sandler turned heads— not always for the right reasons —sporting basketball shorts, a $175 aqua blue hoodie from Aviator Nation (which is already nearly sold out), and a pair of Under Armour Curry 11s (fresh off a re-release).
But when you’re Adam Sandler, you can have a star on the Hollywood Walk of Fame and still dress like you’re making a late-night snack run to Whole Foods.
Sandler’s brand of effortless fashion even earned him the title of Google’s most-searched style icon in 2021. Yes, that Adam Sandler—the man who once layered a hoodie over a Hawaiian shirt at his own movie premiere—is considered a fashion icon by many.
So when Conan O’Brien took the stage on March 2 and roasted Sandler’s Oscars ensemble, the moment practically begged to go viral, complete with a dash of drama and a Timothée Chalamet cameo. Sandler may not have taken home any trophies, but he easily won the night’s unofficial awards for Best Comedic Timing and Most Comfortable Oscars Fit.
Adam Sandler’s casual attire stole the show
Comedian Conan O’Brien had all the time in the world to roast his way through the Oscars’ opening monologue—and he made sure to use every second. One of his prime targets? Adam Sandler, who stood out amongst the black tie crowd. His outfit? A chaotic blend of “Sunday best” and “just remembered it’s trash day.”
“Adam, what are you wearing…You look like a guy playing video poker at 2 AM,” O’Brien quipped.
Sandler, never one to back down from a bit, fired back: “Nobody even thought about what I was wearing until you brought it up! I like the way I look. Because I’m a good person. I don’t care about what I wear and what I don’t wear. My snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front of my peers?”
With that, he made a dramatic exit—ignoring O’Brien’s apology and the audience’s desperate pleas for him to stay. But before leaving, he made sure to issue an unexpected challenge: an impromptu pickup basketball game, calling dibs on “the guy from Nosferatu” (aka Bill Skarsgård, who also happens to be Pennywise, the clown responsible for IT-induced nightmares).
Sandler wasn’t done yet. Before bolting, he showed love to Timothée Chalamet, who was nominated for Best Actor for his role as Bob Dylan in A Complete Unknown.
Chalamet may have left the ceremony empty-handed, but at least he got a consolation prize—a hug and a fatherly-style kiss from Sandler on his way out. If nothing else, he can now officially claim Sandler as his bestie. The comedian’s enthusiastic shout of “CHALAMET!” was a perfect callback to this year’s Emmys, where he hilariously pronounced Timothée’s last name like he was summoning a horror villain.
Award shows can often feel like an eternity of awkward moments and tedious speeches, but O’Brien and Sandler gave us the viral moment we really needed — two comedy legends doing what they do best. Never change, Adam. Never change.
