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Adam Sandler’s Oscars 2025 Outfit Roast: Conan O’Brien Plays Fashion Police
When Adam Sandler showed up to the 2025 Oscars in a hoodie and gym shorts, nobody expected host Conan O’Brien to launch a full-scale fashion intervention—but that’s exactly what happened. The night kicked off with Sandler, ever the king of casual chaos, sporting a neon-blue hoodie that could’ve doubled as a highlighter, paired with gym shorts and sneakers. It was the kind of outfit you’d wear to binge-watch Netflix, not stroll into Hollywood’s most buttoned-up night.
O’Brien, never one to miss a punchline, pounced immediately. “Adam, you’re dressed like a guy playing video poker at 2 a.m. in a gas station parking lot,” he deadpanned, gesturing to Sandler’s front-row seat. The jab was equal parts brutal and hilarious, sparking instant chaos.
But this is Adam Sandler we’re talking about—a man who’s built a career on leaning into the absurd. Instead of shrinking into his (probably very cozy) hoodie, he cranked up the theatrics, shouting back with mock outrage. Cue the Happy Gilmore-esque meltdown we didn’t know we needed. The clash of O’Brien’s dry wit and Sandler’s unapologetic “laundry day” vibe turned the Oscars into a comedy roast no one saw coming—and honestly, we’re here for it.
Sandler, ever the comedic pro, leaned into the bit with a faux-outraged meltdown straight out of a *Billy Madison* sequel. “NOBODY EVEN THOUGHT ABOUT WHAT I WAS WEARING ’TIL YOU BROUGHT IT UP!” he shouted, before storming out—but not without a detour to troll Timothée Chalamet.
The Chalamet Callback: How a Golden Globes Joke Became an Oscars Running Gag
The chaos traced back to the Golden Globes, where host Nikki Glaser joked that Chalamet’s name “sounds like something Adam Sandler would say.”
Sandler, seated in the crowd, immediately shouted “Timothée ah Chalameeeeet!” in his signature goofy drawl.
The bit went viral, and Sandler doubled down weeks later on *Saturday Night Live*—where Chalamet was hosting—by butchering the actor’s name again during an intro. At the Oscars, Sandler couldn’t resist reviving the gag, yelling “CHALAMEEEEET!” mid-exit and hugging a bemused Chalamet. Talk about commitment to the bit.
Sandler’s Red Carpet Rebellion: Defying Oscars Fashion Norms
While Sandler suited up for the Golden Globes, his Oscars look was pure “Sandman” chaos. The hoodie-and-shorts combo split audiences: Was it a disrespectful dress code breach or a genius troll move? Sandler defended his fit mid-tirade: “I like the way I look because I’m a good person. Did my snazzy gym shorts offend you?!”
Fashion critics had a field day, but fans praised the meta-humor. After all, this is the man who made *The Wedding Singer*’s tracksuit jackets iconic.
Why Sandler’s Oscars Antics Worked: Nostalgia Meets Viral Comedy
The moment worked because it felt authentically Sandler—a mix of his man-child characters and his real-life “I don’t care” charm. By dragging Chalamet into the bit, he also tapped into Gen Z’s obsession with the *Dune* star, ensuring maximum meme potential.
O’Brien’s role as the exasperated straight man amplified the comedy, proving that even A-list stars love a well-executed roast.
The Aftermath: Social Media Erupts Over Sandler’s Hoodie Era
Within minutes, HoodieGate dominated Twitter. Memes compared Sandler’s outfit to “post-shower Walmart runs” and “Zoom meeting attire.” Meanwhile, fashion TikTok debated whether the look was a middle finger to red carpet elitism or just… Adam being Adam.
Even designers weighed in: “It’s 2025—if Timothée can wear a backless harness, why can’t Sandler rep gym-core?” argued one commentator.
