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Ranking Adam Sandler’s Starring Roles

One wouldn’t call Adam Sandler an actor with an impressive range. While the comedian has made many, many movies in his decades-spanning career, he’s pretty much played a variation of the same guy: kinda schlubby, a little (sometimes a lot) dumb, and prone to talking in foreign dialects without notice. Someone had to tackle the thankless task of ranking the films in the Adam Sandler oeuvre, so it may as well have been me.

See where you can stream Adam Sandler’s filmography at GoWatchIt, and below find a definitive, completely objective ranking of his movies from best to worst.

1

'Punch-Drunk Love' (2002)

Punch-Drunk Love Adam Sandler
Photo: Columbia Pictures; Courtesy Everett Collection

Compared to the rest of the movies on this list, it feels almost strange to call this an “Adam Sandler movie.” The real lesson here is that the worst P. T. Anderson movie is still the best Adam Sandler movie.

2

'The Wedding Singer' (1998)

The Wedding Singer Adam Sandler
Photo: New Line Cinema; Courtesy Everett Collection

The best Adam Sandler movie not directed by P. T. Anderson, The Wedding Singer answers the question, “How soon was too soon for a period film set in the ’80s?” I’m surprised Michael Ian Black didn’t have a bit part making jokes about Rubik’s Cubes in front of a green screen.

3

'Big Daddy' (1999)

Big Daddy Adam Sandler
Photo: Columbia Pictures; Courtesy Everett Collection

Adam Sandler finally meets his match (in terms of emotional maturity, that is) in Cole and Dylan Sprouse, who share the role of a child who end up on Sandler’s character’s doorstep. For once, a Sandler movie is a tear-jerker not from laughter or pain, but from heartfelt charm. 

4

'Billy Madison' (1995)

Billy Madison Adam Sandler
Photo: Universal Pictures; Courtesy Everett Collection

I wouldn’t say this was a good movie, really, but it is the quintessential Adam Sandler film, as the titular character has the emotional intelligence of a four-year-old and he talks in funny voices, often mimicking inanimate objects. 

5

'Happy Gilmore' (1996)

Happy Gilmore Adam Sandler
Photo: Universal Pictures; Courtesy Everett Collection

“Adam Sandler plays golf, gets punched by beloved game show host” is how I imagine the original treatment for this movie read. Sounds like they had a hit on their hands!

6

'Funny People' (2009)

Funny People Adam Sandler Seth Rogen
Photo: Universal Pictures; Courtesy Everett Collection

Judd Apatow’s film about stand-up comics is secretly a drama about stand-up comics, proving that Adam Sandler does have the emotional range of those two Greek theater masks. 

7

'50 First Dates' (2004)

50 First Dates Adam Sandler
Photo: Columbia Pictures; Courtesy Everett Collection

In this comedy, Drew Barrymore’s character has short-term amnesia and conveniently forgets every time she sees Adam Sandler. If only I were so lucky! 

8

'The Waterboy' (1998)

The Waterboy Adam Sandler
Photo: Buena Vista; Courtesy Everett Collection

This is sort of like Forrest Gump, except without the special effects, the history lessons, the baby boomer-baiting soundtrack, Gary Sinise, the melodrama, or the good acting. 

9

'Spanglish' (2004)

Spanglish Adam Sandler
Photo: Columbia Pictures; Courtesy Everett Collection

A rich white man’s family is forever changed by his Mexican housekeeper. Who better to tackle complicated cultural clashes like the guy who perfected Opera Man?

10

'Reign Over Me' (2007)

Reign Over Me Adam Sandler Don Cheadle
Photo: Sony Pictures; Courtesy Everett Collection

“I am desperate to see a 9/11 drama starring Adam Sandler.” OK, fess up. Which one of you said that, and what dark magical powers do you possess? 

11

'Anger Management' (2003)

Anger Management Adam Sandler Jack Nicholson
Photo: Columbia Pictures; Courtesy Everett Collection

You know that thing where Adam Sandler starts a piece of dialogue really quietly and then he slowly gets REALLY REALLY LOUD AS IF HE’S READING WORDS IN ALL CAPS? That happens a lot in this one. 

12

'The Longest Yard' (2005)

The Longest Yard Burt Reynolds Adam Sandler
Photo: Paramount Pictures; Courtesy Everett Collection

This proves that just because you can remake a Burt Reynolds football comedy (with Burt Reynolds in a supporting role), it doesn’t make it right. 

13

'Click' (2009)

Click Adam Sandler
Photo: Sony Pictures; Courtesy Everett Collection

If you’re lucky, you can use your real non-magical remote to turn this movie right off! 

14

'I Now Pronounce You Chuck and Larry' (2007)

I Now Pronounce You Chuck and Larry Adam Sandler Kevin James
Photo: Universal Pictures; Courtesy Everett Collection

I assume this movie was made with the assumption it could get away with making gay jokes because it’s inherently pro-marriage equality. Hollywood works in mysterious ways! 

15

'You Don't Mess With the Zohan' (2008)

You Don't Mess With the Zohan Adam Sandler
Photo: Columbia Pictures; Courtesy Everett Collection

Sandler clearly was feeling squeezed out of the farty, politically incorrect comedy world once Borat was on the scene, so as punishment the rest of us got You Don’t Mess With the Zohan.

16

'Mr. Deeds' (2002)

Mr. Deeds Adam Sandler
Photo: Columbia Pictures; Courtesy Everett Collection

Sandler plays a small-town poet (hahahahahahahahahahahahaha) who strikes it rich when his uncle leaves him $40 billion. He also somehow gets Winona Ryder to fall in love with him. Isn’t this the best advertisement for an MFA that you can think of?

17

'Little Nicky' (2000)

Little Nicky Adam Sandler
Photo: New Line Cinema; Courtesy Everett Collection

Adam Sandler plays the son of Satan in this autobiographical comedy.

18

'Just Go With It' (2011)

Just Go With It Adam Sandler Jennifer Aniston
Photo: Columbia Pictures; Courtesy Everett Collection

Sandler plays a plastic surgeon who convinces his hot assistant to pretend to be his estranged wife in order to impress his much-younger girlfriend. The title doesn’t just say it all — it kind of represents Sandler’s film career as a whole, don’t you think? 

19

'Bedtime Stories' (2008)

Bedtime Stories Adam Sandler
Photo: Walt Disney Pictures; Courtesy Everett Collection

This is kind of like The Princess Bride, but if the lovable Peter Falk was replaced with Adam Sandler. (Plus, farts.)

20

'Blended' (2014)

Blended Adam Sandler Drew Barrymore
Photo: Warner Bros. Pictures; Courtesy Everett Collection

Drew Barrymore finds herself stuck at a family resort with Adam Sandler and his kids after they go on a terrible blind date. Gee, do you think they will get together in the end? 

21

'Bulletproof' (1996)

Bulletproof Damon Wayans Adam Sandler
Photo: Universal Pictures; Courtesy Everett Collection

Adam Sandler’s Moses gets his feelings hurt when his drug-dealing best buddy turns out to be a cop and busts him. Years later, the same cop must protect him until he serves as a witness in a trial, and the whole thing is very bromantic. 

22

'Eight Crazy Nights' (2002)

Eight Crazy Nights
Photo: Columbia Pictures; Courtesy Everett Collection

Usually Adam Sandler only plays some variation of himself, but in this animated musical comedy about Hanukkah, Sandler also provides the voices for a geriatric couple and a group of deer. 

23

'Grown Ups' (2010)

Grown Ups Adam Sandler Salma Hayek
Photo: Columbia Pictures; Courtesy Everett Collection

This is not a movie about four former SNL cast mates who reunite on a vacation (and bring along Kevin James), but rather a movie about five old guys who used to play basketball together who reunite on a vacation.

24

'Grown Ups 2' (2013)

Grown Ups 2 Adam Sandler
Photo: Columbia Pictures; Courtesy Everett Collection

This is another movie that isn’t about three former SNL cast mates who reunite on a vacation (and bring along Kevin James) after the death of Rob Schneider, but rather another movie about four old guys who used to play basketball together who reunite again — this time without Rob Schneider.

25

'That's My Boy' (2012)

That's My Boy Adam Sandler Andy Samberg

Set in an alternate reality in which child protective services do not exist, Andy Samberg deals with the traumatic childhood experience of being raised by an idiot teenager who grows into an idiot adult played by Adam Sandler. 

26

'Jack and Jill' (2011)

Jack and Jill Adam Sandler
Photo: Columbia Pictures; Courtesy Everett Collection

“Adam Sandler plays his own twin.” Oh, sure, like in The Parent Trap! That doesn’t sound too terrible. “But his twin is a woman.” Ugh, so we’re finally getting the Gap Girls movie no one asked for?