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.

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

The late Dan Baker will serve as an inspiring reminder of what it means to dedicate oneself to a passion. For Baker, that ...

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

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

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, ...

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

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

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

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