You love him or you think he's goofy. Either way, there's no denying Adam Sandler has cranked out some seriously iconic films. Let's rewind the clock and roll through his movies, year by year.
The Early Days (1990s)
Going Overboard (1989) kicked things off with a tiny but hilarious role. Then came the big one: Billy Madison in 1995. Who else could make adulting in kindergarten look that awesome?
The Wedding Singer and The Waterboy arrived in 1998. Both were massive hits. Sandler was officially a comedy king.
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Big Daddy came out the same year. He played a slacker dad, and honestly? Vibes for days. 1999 closed with Deuce Bigalow: Male Gigolo — yes, he was in that one too.
The 2000s Comedy Storm
Little Nicky (2000) had him playing the son of Satan. Weird? Totally. Fun? Absolutely. Then Anger Management (2003) paired him with Jack Nicholson.
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Great Expectations came in 2002, then Click in 2006 hit harder than anyone expected. That remote control movie made everyone cry, didn't it?
50 First Dates (2004) gave us one of the most charming rom-coms ever. Drew Barrymore and Sandler were pure magic. Then I Now Pronounce You Chuck & Larry in 2007 brought Kevin James into the mix.
That's My Boy (2012) and Grown Ups (2010) leaned heavily into his buddy-comedy style. Chris Rock, Kevin James, David Spade — the whole gang was there. Grown Ups 2 followed quickly in 2013.
Adam Sandler | Movies List (1989-2023) - YouTube
The Wild Card Years (2010s)
Then came the Hotel Transylvania series (2012, 2015, 2018). Sandler was Dracula, and kids lost their minds. On Netflix, he dropped Jack and Jill (2011) — playing both twins.
Murder Mystery (2019) paired him with Jennifer Aniston on Netflix. It became one of the platform's most-watched films. Who would've guessed?
The Oscar Buzz Finale (2020s)
Hustle (2022) proved there is another side to Sandler. He played a basketball scout, and critics went wild. Suddenly everyone remembered he's actually a serious actor.
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Lyle, Lyle, Crocodile (2022) and Luxembourg, Luxembourg (2022) showed his range. Leo followed in 2023, a sweet animated gem. Then came You Are So Not Invited to My Bat Mitzvah (2023).
Finally, Happy Gilmore 2 dropped on Netflix in 2025. The sequel fans waited twenty-nine years for. It was worth the wait — and just look at that list!
From goofy frat bro to Oscar-nominated powerhouse, Sandler's filmography is wild. His movies span over three decades of laughter, heart, and absolute absurdity. Don't tell anyone — but you totally just want to binge-watch them all now, right?