Adam Sandler – 10 Best Movies

By Vlad Zakh · April 5, 2026

Adam Sandler’s early films chart the rise of a singular comic voice, from Saturday Night Live standout to box-office staple. Billy Madison has a spoiled man-child repeating grades one to twelve, Happy Gilmore turns a failed hockey player into a golfer, The Wedding Singer falls a 1980s singer for a waitress, and The Waterboy makes an awkward waterboy a college football star. Big Daddy, Mr. Deeds, Punch-Drunk Love, Anger Management, 50 First Dates and The Longest Yard round out the list.

Billy Madison (1995)

TMDB ★ 6.2

Adam Sandler stars as a spoiled man-child who must repeat grades one to twelve to inherit his father's company, in his breakout role.

“Back to school, back to school, to prove to Dad that I'm not a fool.”

Directed by Tamra Davis · 1h 30m · Rated PG-13

Where to watch

Stream: YouTube TV, Starz Apple TV channel · Rent or buy: Amazon Video, Google Play Movies, YouTube

▶ Trailer Letterboxd Netflix Amazon Prime Video YoutubeTV

Happy Gilmore (1996)

TMDB ★ 6.7

A failed hockey player discovers his slapshot translates perfectly to golf.

“The price is wrong, Bob!”

Directed by Dennis Dugan · 1h 32m · Rated PG-13

Where to watch

Stream: Starz, Starz Roku Premium Channel · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Netflix Amazon Prime Video YoutubeTV

The Wedding Singer (1998)

IMDb ★ 6.9 RT 72% Metacritic 60

A jilted wedding-band singer falls for a waitress engaged to the wrong man.

“I want to grow old with you.”

Directed by Frank Coraci · 1h 37m · Rated PG-13

5 wins & 7 nominations

Where to watch

Stream: fuboTV, Paramount Plus Premium, Paramount Plus Essential, Paramount+ Amazon Channel, Paramount+ Roku Premium Channel · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Plex · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Amazon Prime Video YoutubeTV

The Waterboy (1998)

TMDB ★ 6.1

Adam Sandler plays a socially awkward waterboy who becomes a college football star.

“Mama says alligators are ornery because they got all them teeth and no toothbrush.”

Directed by Frank Coraci · 1h 30m · Rated PG-13

Where to watch

Stream: Hulu, YouTube TV, FXNow, TNT, TBS, tru TV · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Amazon Prime Video YoutubeTV Hulu Netflix

Big Daddy (1999)

TMDB ★ 6.5

An immature bachelor adopts a young boy to impress his girlfriend, with predictably chaotic results.

“You can do it!”

Directed by Dennis Dugan · 1h 33m · Rated PG-13

Where to watch

Stream: Netflix, Starz Apple TV channel · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Plex · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Amazon Prime Video HBO Max YoutubeTV

Mr. Deeds (2002)

TMDB ★ 5.9

A small-town greeting card poet inherits a massive fortune and must navigate the corrupt world of big business.

“I fear you are underestimating the sneakiness, sir.”

Directed by Steven Brill · 1h 37m · Rated PG-13

Where to watch

Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Netflix Amazon Prime Video YoutubeTV

Punch-Drunk Love (2002)

TMDB ★ 7.1

Adam Sandler steps away from his usual comedy for a critically acclaimed performance as a lonely, volatile man who finds love.

“I have a love in my life. It makes me stronger than anything you can imagine.”

Directed by Paul Thomas Anderson · 1h 36m · Rated R

Where to watch

Stream: Sony Pictures Core Amazon Channel · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Netflix Amazon Prime Video YoutubeTV

Anger Management (2003)

TMDB ★ 6.2

Adam Sandler plays a mild-mannered man wrongly sentenced to anger management, with Jack Nicholson as the unorthodox therapist.

“You can’t treat people this way and get away with it!”

Directed by Peter Segal · 1h 46m · Rated PG-13

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Amazon Prime Video Netflix HBO Max YoutubeTV Hulu

50 First Dates (2004)

TMDB ★ 6.9

A man falls for a woman whose rare condition means she forgets him every single day.

“Can I have one last first kiss?”

Directed by Peter Segal · 1h 39m · Rated PG-13

Where to watch

Stream: Paramount Plus Premium, Paramount Plus Essential, YouTube TV, USA Network · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Amazon Prime Video Netflix YoutubeTV

The Longest Yard (2005)

TMDB ★ 6.7

Adam Sandler plays a former NFL quarterback who leads a team of inmates against the guards in this sports comedy remake.

"Careful, that’s my throwing arm.”

Directed by Peter Segal · 1h 53m · Rated PG-13

Where to watch

Stream: Paramount Plus Premium, Paramount Plus Essential, Paramount+ Amazon Channel, Paramount+ Roku Premium Channel, Starz Amazon Channel, Starz · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd Netflix Amazon Prime Video YoutubeTV

Streaming availability data from JustWatch, via TMDB. Availability changes often, so check the service before you plan a movie night.

Vlad Zakh

Founder, Movieix

Founder of Movieix. He started the site because most recommendation pages felt like noise. Here, lists are sorted by who's in the film, where it's from and what mood you're in tonight.

Adam Sandler – 10 Best Movies

Billy Madison (1995)

Happy Gilmore (1996)

The Wedding Singer (1998)

The Waterboy (1998)

Big Daddy (1999)

Mr. Deeds (2002)

Punch-Drunk Love (2002)

Anger Management (2003)

50 First Dates (2004)

The Longest Yard (2005)

You might also like

Best 20 American Comedy Movies

6 Best Band Reunion and Rock Comedy Movies

6 Best Modern Parenthood Comedy Movies

6 Best Sudden Windfall and Inheritance Movies

6 Best Wedding Crasher and Runaway Bride Movies

14 Best 90s Romance Movies