How Tom Cruise And ‘Billy Madison’ Helped Adam Sandler Land One Of His Most Acclaimed Dramatic Roles

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Recent Hollywood history is filled with instances of Tom Cruise using his power and influence to shape the business — the most famous example perhaps being his unyielding determinator to have Top Gun: Maverick released in theaters virtually saving the movie business.

Tom Cruise’s fingerprints are basically everywhere you look in modern Hollywood, even in the places you least expect it. For example, it was Cruise who put Adam Sandler in touch with Punch-Drunk Love director Paul Thomas Anderson, which wound up being one of the most acclaimed dramatic roles of Sandler’s career and helped further establish him as a legitimately serious actor.

Cruise and Anderson, one of the most acclaimed directors of his generation, worked together on the 1999 film Magnolia, which represents Cruise’s most recent Academy Award nomination.

“I met Tom Cruise when Nicole Kidman did SNL. Cruise had a Yankee cap dipped down low, and he looked up, and I was, like, in love with him,” Sandler began.

“Tom called me up, and he says, ‘I’m doing a movie with my friend Paul, and he’s a great director and he’s interested in doing a movie with you. Can I put him on the phone?'” he said while on the SmartLess podcast a few years back.

“Paul was very nice, and he’s going, ‘Hey, I loved Billy Madison.’ And I was like, ‘Okay, thanks,’ but I didn’t know who he was. He goes, ‘I just love your movies and your albums. Is it ok if I write you a movie?’ I said, ‘You can do whatever you want man.’ He was sweet. I could tell he was funny.'”

Prior to the release of Punch-Drunk Love, Sandler had exclusively starred in comedic projects. His performance in Punch-Drunk Love, however — which saw him go toe-to-toe with the likes of Philip Seymour Hoffman — changed his reputation as an actor, leading to him landing more dramatic roles in films such as Spanglish, Reign Over Me, Funny People, The Meyerowitz Stories, Uncut Gems, Hustle, and Spaceman.

Eric Italiano BroBIble avatar
Eric Italiano is a NYC-based writer who spearheads BroBible's Pop Culture and Entertainment content. He covers topics such as Movies, TV, and Video Games, while interviewing actors, directors, and writers.