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The 10 Greatest Adam Sandler Movies, Ranked - Maxim

The 10 Greatest Adam Sandler Movies, Ranked

A look back at the insane career of the reigning King of Netflix.
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Did you know that since the premiere of Adam Sandler’s made-for-Netflix movie, The Ridiculous Six, subscribers have streamed over a HALF-BILLION hours of his movies? That’s 500,000,000 hours and it’s an impressive feat for a guy that Forbes counted as one of Hollywood’s most-overpaid actors in 2013. 

Sandler’s recent theatrical releases may have been misfires but he seems to have found his forever home on Netflix, who signed him to a four-movie deal back in 2014 and recently re-upped for another four movies on top of that. 

While we're waiting for Sandler to complete his octet, let's look back on his top ten movies of all time.

10. I Now Pronounce You Chuck and Larry (2007)

One of Sandler’s most socially-minded satires hits the right beats in a lot of ways. Sandler and Kevin James actually have more chemistry here as two firefighters posing as a gay couple than Sandler does with the female leads in some of his other films. The jokes are almost entirely physical but so are Jessica Biel’s scenes and we’re ok with that.

9. Funny People (2009)

A dark, somewhat autobiographical look at the life of a comedian, Funny People’s pedigreed cast (Sandler, Rogen, Jonah Hill and Jason Schwartzman, among others) carry the movie but a long run-time (it’s well over two hours) makes it less re-watchable than most of the movies on this list.

8. Anger Management (2003)

Sandler’s team-up with Jack Nicholson has plenty of high points, mostly when the pair aren't even trying to manage their anger. Jack steals the show here, as you’d expect, but Sandler holds his own in the toe-to-toe flick that doesn’t get enough credit.

7. That’s My Boy (2012)

Casting Sandler to play Andy Samberg’s father was a solid choice. Casting Sandler to play a father who’s also a rock star and genuinely terrible person was a stroke of genius. Letting Sandler and Samberg do their thing in a completely family-unfriendly, R-rated way is why That’s My Boy makes this list.

6. The Wedding Singer (1998)

Sandler’s ode to the 80’s is one of his finest moments. The music, the hair, the genuine connection with Drew Barrymore, the bubbling anger that overflows at the perfectly inopportune moments—this is where Sandler’s style seems to have solidified. It was fresh and charming and remains a favorite to this day.

5. Big Daddy (1999)

Sandler and crew nail this odd-couple story of a man-child having a real child foisted on him. Big Daddy is the kind of movie that you catch on cable and can’t help watching to the end. It’s got memorably funny moments (Hip. Hip pop. Hip hop anonymous?) while also perfectly sticking the heartstring-tug landing.

4. The Waterboy (1998)

Bobby Boucher is a hero, plain and simple. Busting out one of his most ridiculous voices, Sandler’s story of a lowly, podunk waterboy turned college football phenom is about as oddball as he’s ever gotten and we love it. It’s Sandler and co’s slapstick take on everything from Rudy to Varsity Blues. That does not include their take on The Longest Yard though. That was a remake we didn’t need.

3. Airheads (1994)

Technically a Sandler film but made well before he became a star, Airheads’ huge ensemble cast and brilliant story about a struggling band taking a radio station hostage just to get their single played is so overwhelmingly awesome, we couldn’t keep it out of the top three. It’s a subtle reminder of what could have been if Chris Farley was still around. It also reminds us that Brendan Fraser was great and we’d really appreciate it if Sandler would revive his career, maybe in one of those four Netflix movies he just signed up to make.

2. Billy Madison (1995)

It’s not his first movie but we credit Billy Madison as being the movie that launched Sandler’s career as we know it. Never was Sandler’s man-boy shtick more literal as when he played a man who had to redo his K-12 education. Infinitely quotable, hilariously irreverent and perfect for its era, Billy Madison still fires on all cylinders every time you watch it. We’ll never stop looking at you, Swan.

1. Happy Gilmore (1996)

Happy Gilmore took everything that was great about Billy Madison and gave it a huge shot of mass appeal. It’s endlessly quotable ("You eat pieces of shit for breakfast?") It’s utterly memorable (try to forget the Bob Barker fight. We dare you.) It’s funny for all the right reasons and laid the groundwork for Sandler’s charming, determined persona that we see in so many of his movies. Also, it had Carl fucking Weathers as a one-handed golf pro. Sandler movies just don’t get any better than this one.