Thirty years later, the comedy classic’s chill menswear feels more relevant than ever. “I was kind of dressing him as if I wanted him to be cute to college girls,” director Tamra Davis tells GQ.

In a world that’s so cynical, so divided, where everything is examined through a political lens, Sandler is a wisecracking, ...

In Billy Madison, Sandler plays the titular spoiled ... the seeds of the evolving but similar character arcs to come. An Adam Sandler character is usually, if belatedly, all about growing up ...

Adam Sandler knew he had a talent for breaking people up when he was a kid. He was always trying out jokes and gags at the ...

Myung J. Chun via Getty Images Adam Sandler went full Billy Madison during a bit at the 2025 Academy Awards on Sunday night. During his opening monologue, Oscars host Conan O’Brien took it upon ...

Photo illustration by Zachary Scott for The New York Times NBC In 1990, Lorne Michaels hired Adam Sandler for ... name with a leading role in “Billy Madison” in 1995 and later took on ...

They say you can't touch a classic... well, tell that to Adam Sandler. The trailer for Happy Gilmore 2 has finally been ...

Adam Sandler losing his cool at the 97th Academy Awards Sunday night. Myung J. Chun via Getty Images Adam Sandler went full Billy Madison during a bit at the 2025 Academy Awards on Sunday night.