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Adam Sandler’s Movies, Ranked Worst to Best

From ‘Happy Gilmore’ to ‘Uncut Gems,’ the greatest (and most grating) films of the star we call the Sandman

Adam Sandler in various film roles

UNIVERSAL PICTURES; COLUMBIA PICTURES/EVERETT COLLECTION; TRACY BENNETT/COLUMBIA PICTURES

He goes by many names: Billy Madison, Happy Gilmore, Zohan Dvir, Canteen Boy, Opera Man, the Sandman. But ever since the mid-1990s, Adam Richard Sandler has put his God-given moniker above the title of his movies and established himself as one of the major screen comedians of the past 30 years. You may love his angry, abbie-doobie man-children and every-guy heroes, and consider him a comic genius. You might think most of his work is juvenile and ridiculous. You could even make a case for his lack of an Oscar nomination for his role in Uncut Gems qualifying as a prosecutable crime [raises hand]. Regardless, Sandler’s ability to go from standout Saturday Night Live weirdo to human hit factory whose Happy Madison production company netted a multimillion-dollar deal with Netflix has established him as a reliable, consistently bankable superstar.

In honor of fans finally — finally! — getting the long-awaited Happy Gilmore 2, we’ve ranked all of Adam Sandler’s movies to date. Well, most of his movies: We’ve left out the ones in which the Sandman shows up for what’s basically a credited (or uncredited) cameo, so no Coneheads and none of the movies where he lends his mug to a fellow famous actor’s project for a single scene. Ditto the animated movies that just use Sandler’s voice, with one very notable exception. From Billy Madison to Punch-Drunk Love, here are our picks for the best and the worst of the cinema dú Sandman.

1

‘Billy Madison’ (1995)

Before the cinema du Adam Sandler mostly meant bro-baiting, an excuse to showcase friends and family on the big screen, and Netflix-sponsored, phone-it-in paydays, the ex-SNL star gave us this genuinely weird, warped story of a spoiled rich doofus who, in order to stay spoiled and rich, must do the impossible: repeat kindergarten through high school in record time. It remains a masterclass in manchild comedy with Sandler in all his unhinged abbie-doobie glory, fighting off 10-foot-tall penguins and staging elaborate musical numbers that end with operatic pleas for gum. To merely hear someone say “Stop looking at me, swan!” or “That Veronica Vaughn is one piece of ace” or any of the dozens of other beautifully absurd lines is to instantly break into a fit of collective giggles. Not to mention that it features the greatest academic competition to ever end with the words, “I award you no points, and may God have mercy on your soul.” The Sandman had a whole career’s worth of misfits, lunkheads, everydudes and everydads ahead of him when he made this early star vehicle. But he’d never be this simultaneously over-the-top odd and out-and-out hilarious again. —D.F.