Adam Sandler's 15 best movies, ranked (including 'Happy Gilmore')

USA Today

2 days ago

With Adam Sandler, it's been a tale of two careers: the goofy comedian of his "Saturday Night Live" and early film days, and the more accomplished thespian of his later years (who can still be goofy when needed).
But whether or not you prefer his more serious outings to man-child Billy Madison and hockey-loving golf savant Happy Gilmore – who returns in the sequel "Happy Gilmore 2" (streaming now on Netflix) – Sandler has enjoyed a profound evolution as an actor and performer. It's only a matter of time until he nabs an Oscar nomination (and probably should have at least one by now). Who could have imagined that back when he was singing the Hanukkah song on "SNL"?
In honor of his latest outing, we're ranking the Sandman's 15 best movies. (While the original "Happy" makes the cut, the cameo-filled follow-up sadly does not.)
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15. 'Murder Mystery' (2019)
New York cop Nick (Sandler) and hairdresser wife Audrey (Jennifer Aniston) go on their dream European vacation, which goes awry when they're invited on a billionaire's yacht and are embroiled in a murder case. OK, they're no Sherlock and Watson, but Sandler and Aniston end up making a decent detective duo.
14. 'Happy Gilmore' (1996)
The sports comedy is one of Sandler's sillier outings, playing the title hockey player who takes up pro golf to help save his beloved grandma's house. The high-profile cameos, though, are fantastic, from Bob Barker (as himself) brawling with Sandler to Carl Weathers in one of his best roles as Happy's one-handed coach.
13. 'Anger Management' (2003)
In his comedy heyday, Sandler partnered with Jack Nicholson for this buddy flick, with Sandler as a dude sent to therapy after an in-flight incident and Nicholson as the doctor whose unorthodox techniques exacerbate his new patient's rage problems. On paper, it should have been better, but it's still worth watching two A-listers going at it.
12. '50 First Dates' (2004)
"The Wedding Singer" might be the best Sandler/Drew Barrymore rom-com team-up but "First Dates" is the sweetest: A womanizing veterinarian (Sandler) becomes enamored with an art teacher (Barrymore) with amnesia and commits to winning her over day after day.
11. 'Airheads' (1994)
Watching this gonzo music comedy 30 years ago, who could have imagined Brendan Fraser as an Oscar winner, Steve Buscemi with an Emmy and Sandler as a somewhat serious actor? They're cast as hard-rock goofballs who take a radio station hostage with water pistols filled with hot sauce to get their demo tape played.
10. 'Leo' (2023)
Apologies to the "Hotel Transylvania" faithful: A 74-year-old fifth-grade pet lizard is the animated role Sandler was born to play. His title character Leo worries about his mortality and hatches an escape plan but instead makes a bunch of young friends in the delightfully weird and subtly touching musical comedy.
9. 'The Waterboy' (1998)
As a great man once said, "That's some high-quality H2O!" Bullied by the football players he keeps hydrated, mother-loving Louisiana college waterboy Bobby Boucher (Sandler) finally snaps and unlocks an aggressive side that makes him a gridiron wunderkind. He can play outside linebacker for our team anytime.
8. 'The Meyerowitz Stories' (2017)
Writer/director Noah Baumbach's dramedy cast Sandler and Ben Stiller as estranged half-brothers who reunite for an art retrospective for their aging sculptor dad (Dustin Hoffman). A lifetime of dysfunction and a health scare ignite a sibling rivalry that gives both Stiller and Sandler plum complex roles to play.
7. 'Spaceman' (2024)
In a decidedly dramatic yet still oddball role, Sandler plays a Czech astronaut halfway through a lonely, one-man mission to investigate a cosmic purple cloud near Jupiter. Cracks form in the long-distance relationship with his wife (Carey Mulligan), and he works through his feelings by befriending a mysterious talking alien spider (Paul Dano).
6. 'You Are So Not Invited to My Bat Mitzvah' (2023)
Sandler takes a backseat to his real family in this delightful coming-of-age comedy. The role of devoted dad suits him well opposite wife Jackie and daughters Sadie and Sunny, the latter of whom plays a middle-schooler looking forward to her bat mitzvah and instead finds a whole heap of girl drama.
5. 'Funny People' (2009)
Director Judd Apatow's darkly funny yet feel-good dramedy casts Sandler in a role he knows very well: mega-popular comedian/movie star. When he's diagnosed with a terminal disease, Sandler's character befriends a young stand-up (Seth Rogen), reconnects with the love who got away (Leslie Mann) and finds a new lease on life.
4. 'The Wedding Singer' (1998)
The best of Sandler's straight-up comedies is a 1980s retro affair packed with style and cool music. A wedding singer (Sandler) hits it off with a reception waitress (Drew Barrymore) and he promises to play her wedding. Of course, they fall in love, but not without some crises of confidence, Reagan-era high jinks and old-lady rapping to make things interesting.
3. 'Hustle' (2022)
Sandler marries his loves – acting and hoops – as a Philadelphia 76ers basketball scout who discovers a standout streetballer (ex-NBA player Juancho Hernangómez) in Spain and brings him to America. Both help each other out in a rousing narrative chock-full of real-life roundball stars and choice Sandler zingers.
2. 'Punch-Drunk Love' (2002)
Paul Thomas Anderson's romantic dramedy is the first to really toss Sandler in the awards-season mix. The comedian earned a Golden Globe nod as a lonely plunger salesman with serious rage issues who starts dating his sister's co-worker (Emily Watson), though a phone-sex extortion scheme threatens the budding relationship.
1. 'Uncut Gems' (2019)
Get ready for a two-hour anxiety-fest. Josh and Benny Safdie's intricately crafted crime thriller finds Sandler in prime form as a gambling jeweler who wants to make serious bank off a rare opal. He runs afoul of the wrong people, leading to an intensely stressful final act fueled by a close NBA playoff game.