Adam Sandler at 50: Top Five Best and Worst Movies

Most wouldn’t raise an eyebrow if you said that Adam Sandler acted like a man child. And hey, that brand of comedy isn’t for everybody, I get that. But make no mistake: With the exception of Jim Carrey, Sandler was the premier comedic movie star of the 90s. His career has epitomized a roller coaster ride; rising from NYU’s Tisch School of the Arts to Saturday Night Live and stardom, then stumbling through ups-and-downs of semi-hits and flops.

Sandler turns 50 today, which calls for a ranking of his best movies. He’s also got a enough shitty flicks to warrant a ranking of the worst. Here’s a Top 5 list for both. Feel free to comment on any omissions you believe should make the list!


50 First Dates (2004)

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Sure, it’s kinda cheesy, but 50 First Dates remarries the lovable duo of Sandler and Drew Barrymore from The Wedding Singer. It’s funny, it’s romantic, and it features Rob Schneider in a demeaning role. What’s not to love?


That’s My Boy (2012)

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When Donny Berger knocks up his beautiful grade school teacher, he becomes a massive celebrity, only to hit rock bottom. With no option left – in a last ditch effort to discover some sort of meaning in his now meaningless life – he embarks on a mission to save his estranged son (Andy Samberg) from his terrible fiancée. From start to finish, this is a true blue example of horrific acting, writing and directing.


The Waterboy (1998)

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Bobby Boucher is one of the most beloved of all Sandler’s characters, with his stammering and inconceivable play on the foosball field. With so many memorable quotes and characters, The Waterboy is a bonafide classic. F— Gatorade.


Grown Ups 2 (2013)

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Grown Ups’ brand of low-ball comedy somehow raked in hundreds of millions at the box office, and, unfortunately for all of us, resulted in this hard to watch sequel. It’s a star-studded affair that clearly banked on the belief that one of the fundamental keys to box office success is a big-name cast, and cashed in big time. Pray they don’t make a third.


The Wedding Singer (1998)

Hands down one of my favorite movies, and above, where Sandler sings ‘Love Stinks’ by The J. Geils Band is my favorite movie scene of all time. Drew Barrymore and Sandler’s chemistry is electric. In what I believe to be one of Sandler’s best acting performances, set in a believable plot (aside from the part where Billy Idol gives him a hand in first class), The Wedding Singer has a little something for everybody.


Bedtime Stories (2008)

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This movie is hard to watch all the way through, period. It’s a nice thought, where a down on his luck guy has the bedtime stories he tells his niece and nephew come to life. But this one is more of a nightmare to watch than a dream come true.



Billy Madison (1995)

It wouldn’t be a Sandler movie without a far-fetched plot, right? Right. Much like every Sandler movie, the lovable dope faces a menacing task and prevails in the end, winning the girl in the process. This one, however, has a little something extra to it. Plus, it was his breakthrough role. Counts for something, right?


The Ridiculous 6 (2015)

The trailer says it all. I’ve already done you a favor and watched the movie, now do yourself a favor, AND DON’T. Holy cow. So bad, it actually got a zero on Rotten Tomatoes. Let that sink in.

BEST Sandler Movie

Happy Gilmore (1996)

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You could watch this one three times a day and it’d never get old. Happy Gilmore has a place in the heart of every 20-or-30-something in America, and for good reason. All around, the movie is fantastic – the hockey-wannabe turned PGA star needs to win the coveted Gold Jacket from Shooter McGavin – one of the greatest antagonists in any comedy, ever – and wins the girl in the process, who just happens to be Claire Dunphy on Modern Family.

WORST Sandler Movie

Jack and Jill (2011)

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It’s almost as if this idea came to fruition in a pitch and nobody was brave enough to turn it down. Sandler doesn’t play just one horrendous character, he plays that character’s UNBELIEVABLY  ANNOYING TWIN SISTER. This one takes the cake. I’m not sure anyone could even make a counter argument as to why this isn’t one of the worst movies ever made; if you’ve got anything, please, I’m all ears.

Agree with my list? Disagree? Give me your two cents in the comment section.


[Editor’s note: NO BIG DADDY!? I love that movie. Kind of.]

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