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Readers’ Poll: The 10 Best Adam Sandler Movies

‘Billy Madison,’ ‘The Wedding Singer’ and a few real surprises

Adam Sandler in The Wedding Singer

Adam Sandler sings in a scene from the film 'The Wedding Singer', 1998. (Photo by New Line Cinema/Getty Images)

New Line Cinema/Getty Images

Adam Sandler has been confounding critics ever since Billy Madison made $25 million despite scathing reviews. The 48-year-old Brooklyn native has made an astounding amount of movies in the two decades since, and even his most die-hard supporters wouldn't argue they haven't all been winners. (Remember Jack and Jill?) Still, there have been many classics, and now that he signed a four-picture deal with Netflix we asked our readers vote for their favorites. Here are the results.

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10

‘Click’

As in many Adam Sandler movies, there's an odd undercurrent of sadness to Click. The 2006 film tells the story of an overworked father who gets his hands on a magical remote control that allows him to fast-forward through the boring parts of life or use picture-in-picture to watch a baseball game at any time. After skipping family dinners and arguments with his wife, he eventually realizes – too late, it seems – that these are things that make life worth living. The critics tore the film apart, but it still made $237 million.

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9

‘Little Nicky’

Adam Sandler kicked off the new millennium with the most despised movie of his career, a bizarre picture about the three sons of Satan competing to take over hell when their father steps aside. Sandler plays one of the sons that gets cast up to Earth, where he falls in love and learns about good and evil. The actor had won some goodwill the previous few years with Big Daddy and The Wedding Singer, but this set him back a bit. It has, however, developed somewhat of a cult following.

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8

‘Big Daddy’

In Big Daddy, Adam Sandler plays an ill-tempered tollbooth attendant that shuns all adult responsibility until he finds himself caring for a five-year-old whose mother died of cancer. That's a pretty grim setup, but Sandler managed to turn it into a surprisingly sweet and light-hearted movie that grossed nearly a quarter of a billion dollars. It's also one of the best movies Jon Stewart ever appeared in, though that really isn't saying very much.

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7

’50 First Dates’

After the huge success of The Wedding Singer, it was only a matter of time before Adam Sandler teamed up with Drew Barrymore for another romantic comedy. In this 2004 movie, Barrymore plays a woman with a condition that wipes out her memory every morning. That makes it pretty hard to date her, but Sandler gives it his darndest. The film managed to out-gross The Wedding Singer, and the duo's latest flick, Blended, did surprisingly well due to strong overseas sales. If they ever do a fourth, they'll top even Tom Hanks and Meg Ryan.

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6

‘Reign Over Me’

Not every Adam Sandler movie is a comedy with a ridiculous concept, and it's hard to get more serious than the story of a 9/11 widower that gets committed to an insane asylum after trying to commit suicide. The character eventually moves in with his in-laws and picks up the pieces of his life, but it's a heavy story that failed to find a huge audience in theaters. Many people have since discovered Reign Over Me via cable and Netflix. 

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5

‘Billy Madison’

Adam Sandler appeared in a few movies before Billy Madison (and even starred in 1989's low budget Going Overboard), but his modern-day career began around the time he got fired from Saturday Night Live in 1995. It was then that he released this comedy about a lazy, porn-addicted, invisible-Polar Bear chasing heir who repeats every year of grade school in order to take over the family business. It's been shown on basic cable upwards of 10 zillion times, but lines like "If peeing you pants is cool, consider me Miles Davis" remain hysterical.

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4

‘The Waterboy’

Roger Ebert didn't like The Waterboy very much. "Sandler is making a tactical error when he creates a character whose manner and voice has the effect of fingernails on a blackboard," he wrote, "and then expects us to hang in there for a whole movie." The mass public had a very different take on The Waterboy, the tale of a dim-witted football assistant whose hidden rage turns him into a star player. It's a surprisingly sweet story – and the Sandler movie you're most likely to find playing on TBS at midnight on a Tuesday. 

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3

‘Punch Drunk Love’

After finishing the sprawling, three-plus hour Magnolia, writer-director Paul Thomas Anderson was determined to make a simpler movie centered around a single character. That's what lead to Punch Drunk Love, the dark story of a desperately lonely man whose life falls apart after he calls into a phone sex line. The killer cast features Philip Seymour Hoffman, Emily Watson, Luis Guzman and Robert Smigel. Critics were impressed by Sandler's ability to take on a straight role, but the finished product earned far less than most of his wackier films. 

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2

‘The Wedding Singer’

We were a mere nine years away the 1980s when The Wedding Singer hit theaters, but the entire decade already seeming ripe for spoofing. It was a time of neon clothing, big hair and Billy Idol, and The Wedding Singer gleefully mocked all of it. It also provided the backdrop for a very sweet love story between a heartbroken wedding singer and a perky waitress engaged to a complete douche. The movie grossed $123 million on an $18 million budget, and got everyone singing along to the Thompson Twins for the first time in a long time. Also, if you want to feel old, consider the fact that we're much further away in time from The Wedding Singer than the movie was from 1985, the year it mocked. 

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1

‘Happy Gilmore’

After proving he could actually carry a movie with Billy Madison, the Hollywood powers-that-be gave Adam Sandler another starring role. This time around, he played an ill-tempered hockey player who finds that his skills perfectly transferred to golf. His methods weren't traditional and his attitude offended many of the country club elites, but nobody could deny Happy Gilmore's ability to hit a ball down the fairway at lightning speed. If nothing else, the movie gave Carl Weathers a chance to play somebody other than Apollo Creed and the world a chance to see Bob Barker get into a fistfight. 

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