The Definitive Adam Sandler Movie Rankings

In celebration of the 20th anniversary of 'Billy Madison.'

Universal

Adam Sandler ruled my world growing up. His Saturday Night Live characters slayed me, especially Canteen Boy. When Billy Madison came around, I couldn't have been happier. The movie is 89 minutes of Sandler being a complete moron, the glorious theme of my cherished mid-'90s comedies (Dumb and Dumber, Tommy Boy, Ace Ventura). I loved goofiness and Sandler was king.

Since those days, Sandler has continued making movies, over 40 since 1995 when Billy Madison debuted. He's made and starred in a feature-length comedy almost every year since, and, in the process, has become both a very rich man and a critical laughingstock. In Funny People, Sandler plays a character that was great once, but hasn't done anything worthy for a while. He's playing himself. 

I've always had a soft spot for Sandler because of SNL, Billy, and Happy Gilmore. If you told me when I was 14 the comedian would make a movie a year for the next 20 years I would've hugged you. But here we sit, all these years later, and I'm never excited by a new Sandler movie anymore. Have I outgrown him? Has he stopped being funny? What's happened to us, Adam? I thought ranking his movies would help me figure things out. 

Essentially, Sandler flicks boil down to these ingredients: Sandler as a wacky character or family man, an actress way out of his league as the wife/love interest, foul-mouthed kids, shameless product placement, and very famous supporting characters. Like most filmmakers, Sandler's very loyal to his friends/co-stars (except women, who are trophies), casting actors like Allen Covert and Peter Dante in multiple films. He couldn't care less about story. His movies are written around one-note jokes for the most part. It will be a challenge to separate them. But know these rankings come from a place of love. I may not like a lot of Sandler's movies, but it's only because I love others so much. 

[A "Sandler Movie," as defined by the author, excludes his smallest roles and cameos, of which there are many: Dirty Work, Coneheads, and Top Five to name a few.] 

  • Just Go With It

    The Definitive Adam Sandler Movie Rankings
  • Eight Crazy Nights

    The Definitive Adam Sandler Movie Rankings
  • Chuck and Larry

    The Definitive Adam Sandler Movie Rankings
  • Click

    The Definitive Adam Sandler Movie Rankings
  • Grown Ups 2

    The Definitive Adam Sandler Movie Rankings
  • Jack and Jill

    The Definitive Adam Sandler Movie Rankings
  • Blended

    The Definitive Adam Sandler Movie Rankings
  • The Longest Yard

    The Definitive Adam Sandler Movie Rankings
  • Mr. Deeds

    The Definitive Adam Sandler Movie Rankings
  • You Don't Mess with the Zohan

    The Definitive Adam Sandler Movie Rankings
  • Bedtime Stories

    The Definitive Adam Sandler Movie Rankings
  • Bulletproof

    The Definitive Adam Sandler Movie Rankings
  • That's My Boy

    The Definitive Adam Sandler Movie Rankings
  • Grown Ups

    The Definitive Adam Sandler Movie Rankings
  • 50 First Dates

    The Definitive Adam Sandler Movie Rankings
  • Big Daddy

    The Definitive Adam Sandler Movie Rankings
  • Hotel Transylvania

    The Definitive Adam Sandler Movie Rankings
  • Anger Management

    The Definitive Adam Sandler Movie Rankings
  • Reign Over Me

    The Definitive Adam Sandler Movie Rankings
  • Spanglish

    The Definitive Adam Sandler Movie Rankings
  • Little Nicky

    The Definitive Adam Sandler Movie Rankings
  • Airheads

    The Definitive Adam Sandler Movie Rankings
  • Funny People

    The Definitive Adam Sandler Movie Rankings
  • The Waterboy

    The Definitive Adam Sandler Movie Rankings
  • Billy Madison

    The Definitive Adam Sandler Movie Rankings
  • Happy Gilmore

    The Definitive Adam Sandler Movie Rankings
  • Punch-Drunk Love

    The Definitive Adam Sandler Movie Rankings
  • The Wedding Singer

    The Definitive Adam Sandler Movie Rankings

28. Just Go With It  (2011)
I've thought a lot about it, and this is the worst Sandler movie. It's embarrassing on so many levels, watching it will make you want to get deloused. The misogyny and stupid jokes are so rampant, there isn't a redeeming moment available. It's the laziest and most perverted Sandler film, and that's saying a lot.
Domestic box office: $103 million
Rotten Tomatoes: 19%

27. Eight Crazy Nights (2002)
Almost as terrible as Just Go With It, but for different reasons, Eight Crazy Nights was made at a time when Sandler could get away with anything. He went for a holiday movie in typical fashion: mailed-in plot and an onslaught of groan-worthy jokes. Throw in some truly despicable voice work and you've got something nearly impossible to sit through.
Domestic box office: $24 million
Rotten Tomatoes: 12%

26. I Now Pronounce You Chuck and Larry (2007)
A very close contender for the worst is this cricket chirp of a film that becomes more cringe-inducing with each passing year. Sandler and Kevin James are firefighters who get married for insurance reasons. This, of course, gives them an excuse to make every lame gay joke known to man. And Sandler loves gay jokes. His movies are full of them.
Domestic box office: $120 million
Rotten Tomatoes: 14%

25. Click (2006)
This movie hinges on the belief a normal guy can't tell the difference between a TV remote and a remote for a toy helicopter. In his anger, he buys a universal one from, wait for it, Bed, Bath and Beyond. Click proves how an interesting idea (losing control of time) can be made obsolete by the unimaginative writing around it. Sandler doesn't pause time to save the world, he does it to fart in the boss' face. 
Domestic box office: $137 million
Rotten Tomatoes: 32%

24. Grown Ups 2 (2013)
Perhaps, never in the history of film has there been such an unnecessary sequel. 
Domestic box office: $134 million
Rotten Tomatoes: 7%

23. Jack and Jill (2011)
Jack and Jill looks like one of the fake movies in Funny People. It would probably be my worst pick if it wasn't filled with unintentional humor. It's one of those terrible movies everyone should see. Sandler plays brother and sister. It's amazing it was ever made.
Domestic box office: $74 million
Rotten Tomatoes: 3%

22. Blended (2014)
Like Grown Ups 2, this film is totally unnecessary. It's Sandler's third romantic comedy with Drew Barrymore and the one that proves the chemistry is gone. The kids in this are especially unlikable, but Terry Crews does have a couple funny moments. Sandler has none. He's officially an unfunny dad.
Domestic box office: $46 million
Rotten Tomatoes: 14%

21. The Longest Yard (2005)
A remake of the Burt Reynolds original, Sandler's Longest Yard is just an excuse to get a bunch of athletes in a movie for fun. It does nothing to distinguish itself. It feels corporate because it's without character (and the ESPN signs everywhere don't help). On the plus side, Sandler makes a pretty good ex-quarterback.
Domestic box office: $158 million
Rotten Tomatoes: 31%

20. Mr. Deeds (2002)
After Big Daddy, Sandler started devoting himself full-time to churning out weak imitations of Frank Capra films. Mr. Deeds is an actual remake of a Capra film, but without a whiff of the director's gift for emotional resonance. Sandler's movie contains one of the actor's worst characters: the slack-jawed yokel Longfellow Deeds. He writes dumb poetry and punches people he doesn't like.
Domestic box office: $126 million
Rotten Tomatoes: 22%

19. You Don't Mess with the Zohan (2008)
Even if it's not funny, and Zohan is very not funny, it's at least harder to knock Sandler when he takes some risks creating a comedic character. He's trying here and that's better than just remaking someone else's movie.
Domestic box office: $100 million
Rotten Tomatoes: 37% 

18. Bedtime Stories (2008)
This PG family movie is like the melodramatic last act of Sandler's comedies, except stretched out to 100 minutes. It's hugely cheesy, but the jokes actually work better than in many of his comedies because the tone is so much softer. It was a step in the right direction, family-wise.
Domestic box office: $110 million
Rotten Tomatoes: 25%

17. Bulletproof (1996)
A blip on the map of Sandler's career, Bulletproof is a relic of a lost time, when Damon Wayans and Adam Sandler were the two biggest comedic stars in the world. They were paired together like Nolte and Murphy in this action thriller by the director of Juice. It's a formulaic movie, but Sandler has some funny moments, especially his rendition of "I Will Always Love You" in the shower.
Domestic box office: $22 million
Rotten Tomatoes: 8%

16. That's My Boy (2012)
I have a weak spot for That's My Boy because it's full of New England humor and accents. I recognize it's terrible but I love Sandler for playing this degenerate, rated R version of Billy Madison after age 40. The movie comes undone thanks to the usual Sandler easy jokes and cheese (plus a whiny Andy Samberg), but there's a funny streak in this one that other Happy Madison (Sandler's production company) movies hadn't had in years.
Domestic box office: $37 million
Rotten Tomatoes: 20%

15. Grown Ups (2010)
It just feels fake. There's so little writing it's frustrating because there's a lot of potential in Grown Ups. Five funny guys who are friends in real life should have a natural, flowing chemistry. But, instead, Grown Ups has no rhythm. It has too many wives and kids running around to be coherent and too many canned jokes. This movie should be rated R and focus on the five comedians. I'm sure Sandler, James, Chris Rock, David Spade, and Rob Schneider sitting in a room and talking would be more entertaining. 
Domestic box office: $162 million
Rotten Tomatoes: 10%

14. 50 First Dates (2004)
It feels like a real movie, an accomplishment for a Sandler comedy. And, actually, 50 First Dates is much more of a romance than a comedy. Sandler plays worried, concerned, and romantic in his attempts to get Barrymore, who plays a forgetful beauty, to remember him. Sure, it's totally lame, but it's also likable.
Domestic box office: $120 million
Rotten Tomatoes: 44%

13. Big Daddy (1999)
Big Daddy was the first movie that predicted Sandler's future career path towards family-oriented comedies with terrible cheeseball endings (because it made tons of money). But we'll forgive the cheeseball ending in Big Daddy since most of it is endearing. Sandler plays the self-centered guy who befriends a kid and it changes his life. The jokes are stupid and the ending stupider, but Sandler pulls it off somehow.
Domestic box office: $164 million
Rotten Tomatoes: 40%

12. Hotel Transylvania (2012)
I probably like this movie a little more than most because it marked a stark improvement for Sandler and his guys in the family movie department. Sandler's voice work is much-improved from Eight Crazy Nights and the movie works on a very basic level. It's nothing compared to Pixar or Disney's stuff, but it's a solid Sandler film. 
Domestic box office: $148 million
Rotten Tomatoes: 45%

11. Anger Management (2003)
Jack Nicholson's pain in the ass anger management guru will test your patience as he tests Sandler's in this 2003 comedy. If you can stand him, you'll enjoy seeing the mismatched pair face-off in scene after scene. Dave Buznik is one of Sandler's most likable characters and one made for him: a guy constantly on the brink of rage stifling it every minute.
Domestic box office: $136 million
Rotten Tomatoes: 43%

10. Reign Over Me (2007)
Sandler creates one of his best characters in this buddy drama that co-stars Don Cheadle. The goofball plays a damaged widower who lost his family on 9/11 and is still an emotional basket case four years later. A reunion with his former roommate (Cheadle) helps bring him back to life.
Domestic box office: $20 million
Rotten Tomatoes: 64%

9. Spanglish (2004)
Despite how emotionally-manipulative this movie is (and how brutally obnoxious Tea Leoni's character is), Spanglish has some great moments. For once, Sandler is actually believable as a romantic lead as he falls in love with his beautiful housekeeper when his wife strays from the nest. 
Domestic box office: $43 million
Rotten Tomatoes: 53%

8. Little Nicky (2000)
Forgive me Movie Gods, I like Little Nicky. This is my most controversial choice. Again, I like when Sandler takes risks with characters and creates something original... somewhat original anyways. I acknowledge the plot is ludicrous, but it's too much fun watching Sandler snarl through a hugely weird performance as Satan's weak-ass son. "Release the good!" So stupid and funny.
Domestic box office: $39 million
Rotten Tomatoes: 22%

7. Airheads (1994)
The somewhat forgotten Sandler movie, Airheads cast the fledgling actor when he was still on SNL and in his prime. He plays the drummer in a band who takes a radio station hostage and he steals every scene he's in. It's also the origin of Sandler's working friendship with the great Steve Buscemi.
Domestic box office: $6 million
Rotten Tomatoes: 21%

6. Funny People (2009)
If Funny People didn't end so horribly, it might be in the top three, but it's still one of Sandler's best movies. The first two acts are beautifully-written and full of the hilarious characters the film's title promises. It's also Sandler's lone satire as he plays a version of himself: a rich, famous actor who's still making money, but who's lost touch with the funny.
Domestic box office: $158 million
Rotten Tomatoes: 68%

5. The Waterboy (1998)
Even after Billy Madison and Happy Gilmore, Sandler found a way to create another character with hilarious rage issues. I love Bobby Boucher, the tackling savant who lives a sheltered existence with his Mommie Dearest in Lousiana's bayou. This was the movie that made Sandler a household name.
Domestic box office: $161 million
Rotten Tomatoes: 35%

4. Billy Madison (1995)
The one that started it all was one of my favorites as an impressionable youth. Billy is the ultimate Sandler movie because it contains all the comedian's gibberish sayings and gesticulations in one place. It's based around an absurd premise, but Sandler takes over so hardcore it doesn't matter what happens in the story. It's also his most quotable movie.
Domestic box office: $26 million
Rotten Tomatoes: 46%

3. Happy Gilmore (1996)
Sandler's follow-up to Billy Madison had a bigger budget, but more of the same great Sandler comedic anger. His hair-trigger temper as a hockey player-turned-golf pro creates big laughs and Happy contains the best supporting performance by any actor in a Sandler movie: Christopher McDonald as Shooter McGavin. 
Domestic box office: $39 million
Rotten Tomatoes: 60%

2. Punch-Drunk Love (2002)
Barry Egan is Sandler's greatest accomplishment as an actor. Working with one of the world's best directors, Paul Thomas Anderson, will do that for you. Punch-Drunk has low lows, but they make the highs soar that much higher. Sandler is sweet and funny as a complete loser who finds love unexpectedly and with it, a new reason to live.
Domestic box office: $18 million
Rotten Tomatoes: 79%

1. The Wedding Singer (1998)
The most well-rounded, universally-appealing Sandler film, The Wedding Singer is his best movie for a lot of reasons. First, It's set in the '80s. Second, it's full of the actor's trademark angry humor as well as his silly humor, but they don't take over the story like in Billy and Happy. It's a real movie. His character, Robbie Hart, is hugely sympathetic as the left-at-the-altar good guy who finds love with a sweet waitress (Barrymore), but must bide his time. She's engaged to a nightmare of a human being (the fantastic Matthew Glave as Glenn Guglia). The love story is beautifully-handled; the humor is well-timed; and the movie boasts Sandler's most satisfying ending.  
Domestic box office: $80 million
Rotten Tomatoes: 67%

Senior Editor at Zimbio. I'll take Johnny Clay, the Rev. Harry Powell, and Annie Savoy. You can have the rest.
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