The "Happy Gilmore" star was dressed in his usual hoodie and baggy basketball shorts for a funny bit with host Conan O'Brien at the Academy Awards.

The 'Happy Gilmore' actor is notorious for his laid-back style — and Timothée Chalamet got in on the bit, too.

Adam Sandler is crashing the biggest party in Hollywood! The actor made a surprise appearance at the 97th Academy Awards, ...

In a rare crossover between the Golden Globes & the Oscars, Adam Sandler was part of both ceremonies' opening monologues for ...

The 'Happy Gilmore' actor showed up to Hollywood's biggest night in a low-key look by the Venice sweats label.

Adam Sandler attended the 2025 Oscars in true Adam Sandler fashion and, despite being called out for looking too casual, ...

Adrien Brody-Halle Berry recreated their viral 2003 kiss, while Daryl Hannah showed her support for war-ravaged Ukraine X ...

Adam Sandler made an unforgettable surprise appearance at the 97th Academy Awards, turning heads with his ultra-casual outfit ...

The highly anticipated Oscars kicks off tonight, hosting this year's best films and the world's wealthiest actors.

Conan O’Brien poked fun at Karla Sofia Gascon's past-Tweet controversy in his Oscars opening monologue. The 61-year-old comic ...

During the Oscars 2025, Adam Sandler wore a sweatshirt and went to hug Timothee Chalamet, interrupting Conan O'Brien's speech ...

Adam Sandler made a wild appearance in this year's Oscars ceremony during Conan O'Brien's opening monologue -- dressed in a bright blue hoodie and shorts.