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The best Adam Sandler movies, ranked

In these Adam Sandler movies, the native New Yorker gives dozens of worthy performances, from slapstick to dramatic

Funny People

Love them or hate them, Adam Sandler movies are a theater fixture. Whether he’s working in a tollbooth or not working at all, delivering the essential pizza to the hungry or stumbling into an inheritance, the funnyman has been dominating the comedy scene since he played a buddy of Theo’s on The Cosby Show. He may not be one of the best comedians of all time, but the Saturday Night Live alum has earned well over a hundred credits for writing, producing and starring in bathroom-humor blockbusters and toned-down dramatic flicks alike, and he recently inked a deal for four movies on Netflix. With more than four dozen titles to choose from, Sandler’s résumé is a doozy, but it wasn’t hard to eliminate a whole slew of ’em—Jack and Jill, Just Go With It, Bedtime Stories, Pixels—for our list of his best movies of all time.

Best Adam Sandler movies

1

The Wedding Singer (1998)

Who could resist the smooth, crooning notes of Sandler as Robbie Hart or the fresh-faced charm of Drew Barrymore? This ‘90s throwback throws it back even further to ‘85 for a nostalgia-fueled karaoke session (and questionable fashion choices).

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2

Big Daddy (1999)

Sonny Koufax is living the dream—he barely has to work, lives in a sweet NYC loft and hangs out with his weird friends all day long. Sonny Koufax is our idol, basically. Though we probably would have done more than lay down newspapers when the kid wet the bed.

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3

Billy Madison (1995)

If you deny singing Billy’s “Back to school” song on the first day of school every year (or using it as an Insta caption), you’re lying. Sandler and all his buddies make knee-slapping appearances in this one with more quotable scenes than we know what do to with. O’Doyle rules!

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4

Happy Gilmore (1996)

Before we loved her as Claire Dunphy on Modern Family, Julie Bowen was PR pro Virginia Venit in Sandler’s hilarious sports comedy about aspiring ice hockey player turned accidental golfer. The fight between Sandler and Bob Barker (as himself) won the flick an MTV Movie Award. (It’s not an Oscar, but still.)

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5

Click (2006)

You know this Sandler movie as the one that made your boyfriend tear up, even though he totally denies it now. The genius of Christopher Walken aside, this film unexpectedly pulls at the heartstrings and simultaneously has you counting your blessings and wishing for that remote to be real—and in your hand.

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6

Funny People (2009)

Judd Apatow’s writing and direction took this decidedly somber flick from possible disaster to heart-tugging and poignant, and we love him for it. His wife, Leslie Mann, joins Seth Rogen and Sandler in unexpectedly well-executed, semi-serious leading roles that manage to merge the Big C and endless funnies.

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7

Spanglish (2004)

The language barrier isn’t the only challenge on the way to the funny in this one, directed by James L. Brooks—Sandler plays chef John Clasky, who wins himself a bit of fame and a chunk of change thanks to his top-notch cooking chops. His new housekeeper is Mexican immigrant Flor (Paz Vega), who moves in with the Claskys with her daughter in tow.

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8

Punch-Drunk Love (2002)

The funnyman shows off a different side in this comedy-drama-thriller. Business owner Barry Egan still doesn’t have much to be happy about in life, which his seven sisters never let him forget. Things almost start to look up when a new woman gets his attention, but another newcomer to Barry’s life threatens everything.

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9

Grown Ups (2010)

Five old friends reunite over the death of their former coach and realize how much a few decades can change things. Sandler, Chris Rock, Kevin James, David Spade and Rob Schneider flounder on the performance front, but nostalgia and good ol’ bad humor rank high regardless.

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10

50 First Dates (2004)

The Wedding Singer duo make magic again—or something sort of like it—in this unpretentious charmer. He’s a hit-and-quit type; she can’t remember a thing come breakfast. His daily attempts to make her fall in love and recover from amnesia are alternatingly sweet and nauseating, which is pretty typical of Sandler’s slapstick.

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11

I Now Pronounce You Chuck and Larry (2007)

To give credit where it’s due, this film tried to do something for marriage equality, but the stereotypical jokes are more misses than hits. Kevin James and Sandler are firefighters and buddies who partner up to cheat the system, and Jessica Biel wears tight skirts. Ugh.

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12

Anger Management (2003)

As most half-decent comedies do, this one starts with a misunderstanding. It lands a regular guy in the office of Jack Nicholson’s Dr. Buddy Rydell, a therapist of questionable ethics and methods to overcome an anger problem he doesn’t have, until of course his entire life is thrown out of balance.

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13

Mr. Deeds (2002)

We won’t deny the cringeworthiness of some of the gags in this one, but Winona Ryder’s sweet and sassy Babe Bennett balances out Sandler’s goofy Longfellow Deeds to bring up some wholehearted belly laughs. The caricatures of characters on the sidelines induce eye-rolls and chuckles at the same time.

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14

The Longest Yard (2005)

In a remake of the 1974 Burt Reynolds flick, Sandler plays Paul Crewe, a former NFL player and current inmate. The original Crewe (Reynolds) returns, this time as a fellow inmate and former college player who helps Crewe train a ragtag group of prisoners for the big game versus the warden’s team.

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15

The Waterboy (1998)

Bobby Boucher is one of Sandler’s unlikeliest heroes, but a hero (of sorts) he is nonetheless, if only for his ability to win the affection of Vicki Vallencourt and give Henry Winkler something to do in his twilight years. Key to enjoying The Waterboy is not thinking too much about why it’s making you laugh.

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