Conan O’Brien Mocks Adam Sandler’s Oscars Look: ‘I Like My Style’

The 97th Academy Awards, held on March 2, 2025, was filled with glamorous red-carpet moments, emotional speeches, and big wins, but one of the night’s most unexpected highlights came when Adam Sandler made a surprise appearance—dressed in his signature casual attire. While the Oscars are known for their extravagant fashion, with A-list celebrities donning custom designer outfits worth thousands of dollars, Sandler once again demonstrated his unique style choices.

Sandler’s Laid-Back Fashion Statement Stands Out at Hollywood’s Biggest Night

Sandler, famous for his no-fuss wardrobe of oversized T-shirts, gym shorts, and sneakers, stayed true to his style as he attended the prestigious ceremony in a baby blue zip-up Aviator Nation hoodie, a Hawaiian shirt, loose basketball shorts, and colorful sneakers. The contrast between his ultra-casual outfit and the lavish tuxedos and gowns worn by the other guests instantly made him a talking point at the star-studded event.

His fashion choice was all the more noticeable because the Oscars have long been associated with high-end luxury fashion, with stylists spending weeks curating the perfect red-carpet look for nominees, presenters, and attendees. Yet, Sandler effortlessly stole the spotlight just by showing up in what looked like his regular weekend outfit—one that might be more suited for a late-night trip to a gas station rather than Hollywood’s biggest awards ceremony.

Conan O’Brien Calls Out Sandler’s Outfit in a Hilarious Oscars Monologue

Host Conan O’Brien, making his much-anticipated debut as the Oscars emcee, wasted no time pointing out Sandler’s unconventional outfit in his opening monologue. Known for his sharp wit and quick humor, O’Brien turned the comedian’s casual look into one of the night’s funniest moments.

“For such a prestigious night, it’s important that everyone is properly dressed,” O’Brien said, setting up the joke before shifting his attention to Sandler.

With a mischievous grin, he added, “Adam Sandler, however, looks like a guy playing video poker at 2 a.m.”

The audience erupted into laughter as the camera panned to Sandler, who—true to his comedic nature—played along, throwing up his hands in mock protest.

Sandler Fires Back with a Classic Comeback

Rather than letting the joke pass without a response, Sandler, well-known for his comedic timing, took the opportunity to turn the moment into an even funnier exchange.

“Nobody even thought about what I was wearing till you brought it up!” he yelled back at O’Brien, pretending to be offended.

The audience, including Hollywood’s biggest stars, was visibly entertained as Sandler continued his playful rant.

“I like the way I look because I’m a good person. I don’t care about what I wear or what I don’t wear,” he added, leaning into the bit. “Did my snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front of my peers?”

O’Brien, ever the showman, quickly backpedaled, pretending to apologize as the audience laughed along.

Sandler Pretends to Walk Out, Then Invites Stars to a Basketball Game

In an exaggerated display of faux indignation, Sandler then stood up as if he were about to storm out of the venue, prompting even more laughter from the crowd. But just as he reached the aisle, he paused, turned around, and delivered one final punchline that sealed the moment as one of the most talked-about highlights of the night.

“You are all welcome to join me for a game of five-on-five basketball,” he said with a smirk, referencing his love for the sport.

The audience, already captivated by the comedic exchange, burst into applause as O’Brien laughed and moved on with his monologue.

Adam Sandler: Hollywood’s Unofficial King of Comfort

While Sandler’s laid-back Oscars look may have shocked some viewers, longtime fans know that this is far from an unusual choice for the comedian. Over the years, he has developed a reputation for consistently opting for comfortable, oversized streetwear, no matter the occasion.

Unlike other celebrities who regularly appear on red carpets dressed in designer suits, Sandler has built an entire brand around not caring about fashion. His go-to look—baggy shorts, sneakers, and hoodies—has even earned him admiration from Gen Z, who see his “no-effort” style as both relatable and iconic.

GQ Magazine once dubbed him “the no-f*cks-given style god,” praising his ability to prioritize comfort over couture. With his latest Oscars appearance, Sandler has further cemented his status as Hollywood’s most effortlessly dressed star.

Conan O’Brien Shines as Oscars Host with a Sharp and Witty Monologue

Beyond the playful Sandler moment, Conan O’Brien’s hosting debut was met with praise. Known for his decades of experience in late-night television, O’Brien delivered a monologue packed with well-crafted jokes, timely observations, and affectionate jabs at Hollywood’s elite.

One of the standout jokes came when he addressed the Best Picture nominee “Anora,” a film that made headlines for its record-breaking use of profanity.

“‘Anora’ uses the F-word 479 times,” O’Brien said. “That’s three more than the record set by Karla Sofía Gascón’s publicist,” he joked, referencing the actor’s controversial social media presence during the awards season.

O’Brien also touched on the Los Angeles wildfires that recently impacted the industry, striking a more serious tone to acknowledge the resilience of the filmmaking community.

“For almost a century, we have paused every spring to elevate and celebrate an art form that has the power, at its very best, to unite us,” O’Brien said. “Even in the face of terrible wildfires and divisive politics, the work continues.”

Oscars 2025: Notable Wins and Emotional Moments

Beyond the laughs, the 97th Academy Awards delivered several historic moments and emotional victories.

• “Anora” dominated the evening, winning Best Picture, while Mikey Madison took home Best Actress for her role in the film.
• Adrien Brody won Best Actor for his performance in “The Brutalist,” which also secured awards for Best Cinematography and Best Original Score.
• Kieran Culkin, winning Best Supporting Actor for “A Real Pain,” made headlines with his heartfelt speech, in which he jokingly promised his wife they would have a fourth child.

The night was a perfect blend of humor, heartfelt tributes, and memorable wins, solidifying the 2025 Oscars as one of the most entertaining ceremonies in recent years.

Adam Sandler’s Style Wins the Night

While the Academy Awards celebrate the best in filmmaking, Adam Sandler unintentionally became one of the biggest talking points of the night—simply by staying true to himself. His casual look may have been the subject of jokes, but ultimately, it only reinforced what makes him so beloved: his authenticity, humor, and refusal to conform to Hollywood norms.

And if there’s one lesson to take away from the 2025 Oscars, it’s this: fashion fades, but Sandler’s love for basketball shorts is forever.