The Comedy Icon Storms Out of the 97th Academy Awards on March 2, 2025, After Host Conan O’Brien Roasts His Signature Hoodie-and-Shorts Look, but Not Before Planting a Playful Smooch on Timothée Chalamet During a Hilarious Monologue Cameo.
Los Angeles, USA – March 4, 2025 – Adam Sandler turned the 97th Academy Awards into his own playground Sunday night, crashing host Conan O’Brien’s opening monologue with his trademark laid-back style before dramatically exiting the Dolby Theatre—leaving a trail of laughs and one very surprised Timothée Chalamet in his wake. The Happy Gilmore star, not nominated this year but ever the showman, became the night’s unexpected MVP on March 2, sporting a roomy Aviator Nation hoodie, Hawaiian shirt, below-the-knee basketball shorts, and colorful sneakers—a “Sandler fit” that promptly drew O’Brien’s ire and set off a chain of events that lit up the Oscars broadcast.
It all started when O’Brien, midway through a sharp-tongued monologue, zeroed in on Sandler’s casual attire. “Adam, what are you wearing?” the host jabbed, as the camera panned to Sandler in the audience, grinning sheepishly. “You look like a guy playing video poker at 2 AM!” The crowd roared, but Sandler fired back: “Nobody cared until you brought it up, Conan! I like how I look—I’m a good person!” The exchange escalated when Sandler, feigning offense at being “mocked in front of my peers,” stood up, announced he was leaving, and invited the room to a midnight basketball game at Veterans Park—bungling Nosferatu as “Nosterafu” in the process. On his way out, he wrapped Chalamet, nominated for Best Actor in A Complete Unknown, in a bear hug and planted a kiss on his head, a callback to Nikki Glaser’s Golden Globes quip about Sandler yelling “Chalamet!” in his signature goofy voice.
Backstage, O’Brien later told The Hollywood Reporter the bit was Sandler’s brainchild. “That was all Adam—he pitched it, and I just ran with it,” he said, marveling at how the 58-year-old turned a roast into a live-wire moment. Chalamet, who lost to Adrien Brody (The Brutalist), took it in stride, laughing it off at the Governors Ball with girlfriend Kylie Jenner. “Adam’s a legend,” he told reporters. “I’ll take a kiss from him any day.”
The cameo capped a stellar Q1 for Sandler, who’s been juggling Happy Gilmore 2 filming—where he recently bonded with NFL star Travis Kelce—and a reflective SNL 50 tribute song last month that even drew a shoutout from Kanye West. His Oscars antics doubled as a cultural flex: the hoodie-and-shorts combo, dubbed “Sandlercore,” has Gen Z fans chronicling his fits online, while his storm-out nodded to his everyman charm. “I don’t care what I wear—I’m here for the vibes,” he’d told GQ earlier, a mantra he lived out loud Sunday.
Not everyone was amused. Some X posts decried the kiss as “awkward,” others called his exit “disrespectful” to nominees like Mikey Madison, who won Best Actress for Anora. But most saw it as peak Sandler—unscripted, unpolished, unstoppable. At the Vanity Fair afterparty, he posed with wife Jackie, unfazed by the night’s chaos. “Conan started it,” he quipped, sipping a drink. Whether shooting hoops at midnight or prepping his next Netflix hit, Sandler proved once again: he doesn’t need a tux—or an Oscar—to own Hollywood’s biggest stage.
