‘Billy Madison’: The one Adam Sandler movie he would take to a deserted island

Posted On September 23, 2025September 23, 2025

There’s little doubt that Adam Sandler reached the point where he no longer gives a hoot what anyone, anywhere thinks of him, or his films, quite some time ago.

You can tell this from the way he tends to carry himself and the fact he wears whatever he likes, and it’s always some kind of hugely oversized basketball attire, an ensemble carried into in his movies as well, as evidenced recently by Happy Gilmore 2. Over the last ten to 15 years, he has certainly made and released films simply because he thought they represented a funny idea, despite them being some of the worst-reviewed in cinema history. 

But the simple fact is, Sandler has earned the right to wear, do and make whatever he likes by virtue of the fact that in his 20s, he produced some of the most popular, most enduring comedies of the modern era, and as a byproduct, made an absolute shedload of cash doing it. 

They may not have usually been particularly well received by critics, even on release, but almost 30 years after movies like The Waterboy, Happy Gilmore and The Wedding Singer, they are still some of the most-watched on Netflix, and a standard choice for anyone stuck at home, either feeling a) sick or b) hungover. 

Happily, Sandler by all accounts is one of the nicer men in Hollywood; he donates millions to charity, is pleasant to fans when he meets them and generally likes to keep a low profile without making a fuss of his celebrity, so you won’t hear anything bad about him from us. 

In rare moments, he has also proven he doesn’t just do dumbed-down comedy, for as far back as 2002, he was winning acclaim for his work in the Paul Thomas Anderson romantic drama Punch Drunk Love, and he repeated the trick in 2018 in the brilliant Safdie Brothers thriller Uncut Gems.

That was a career high performance from Sandler, who picked up a Critics’ Choice award nomination for his portrayal of a New York jeweller in way over his head, thanks to a gambling addiction and the purchase of a black opal he believes could be worth a million dollars. The film is now a regular in many lists of the best movies this century, and the actor is uniquely superb in a role that his management had initially rejected, only relenting once Martin Scorsese was attached as an executive producer and Jonah Hill had dropped out of playing the lead. 

Since then, Sandler has penned a new mega-money deal to make films exclusively for Netflix and is working on another Safdie Brothers project. But the film he looks back on most fondly is one of his original comedy hits, the 1995 feature that he co-wrote and has since spoken of as the one movie he would take to a desert island.  

He told The Harvard Crimson: “I’d take Billy Madison. It was the first one; it was the one that got my own vision out there. It was my mother’s favourite one. You know what, though, I’d like to hang out with Bobby Buscet (the character’s name in The Waterboy). I’d let Bobby [put] his head on my lap and sleep.”

Billy Madison is the story of a young man trying to prove he is worthy of his father’s inheritance in running the family company by having to repeat the first grade of elementary school. It wasn’t well reviewed on release but proved a hit with audiences, doubling its budget and has since gone down as a ‘90s comedy staple. This year, Sandler is getting considerable attention for his performance in Noah Baumbach’s latest movie, Jay Kelly, alongside George Clooney and Laura Dern. The movie is due for release in the UK in November and should see him in one of those rare moments of dramatic flair. 

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