The 10 Best Adam Sandler Movies of All Time

Adam Sandler has been a controversial figure in the comedy sphere for the past few decades. Not because he has said anything that might get him in trouble, but because there are many who find him untalented or unfunny. Films like Grown Ups 2 or Jack & Jill have left a bad taste of Sandler in many people’s mouths, one that’s hard to shake.

But is Sandler really that unfunny? Does his role in Pixels mean he is untalented? If that’s true, then so is Peter Dinklage, and no Game of Thrones fan would say that… Instead, we’ve put together a list of the best Adam Sandler movies out there. Check it out below and have your faith restored in the great man! 

1. Billy Madison (1995)

Maybe the most outlandish of Adam Sandler’s filmography (though that’s certainly up for debate), Billy Madison follows the lazy and entitled titular character (naturally played by Sandler) as he struggles to inherit his father’s hotel empire by completing 1st through 12th grades. Sandler is joined by Darren McGavin (Kolchak: The Night Stalker), who plays Billy’s retiring father, Bradley Whitford as Eric Gordon, Madison’s rival for his father’s company, Bridgette Wilson as Veronica Vaughn, Madison’s love interest, and Norm Macdonald as his good friend Frank.

This one is a lot of fun, and certainly one of the zaniest on this list. Sandler does here what he does best, play an unsympathetic character who quickly becomes one. There are a lot of little fun things that make this movie a classic, including a former pro-wrestling principal and a school decathlon, but no one shines brighter here than Sandler himself (though recurring Sandler co-writer Tim Herlihy does his best).

Billy Madison was one of Sandler’s earliest hits that helped put him on the map, making him a household name almost overnight. We can’t understate how good this flick is.

2. Uncut Gems (2019)

Sandler’s breakout dramatic role shook audiences around the world, proving that his acting chops are a lot bigger than initially thought. Uncut Gems follows Howard Ratner (Sandler), a New York Jewish-American with a strong gambling addiction who must retrieve an expensive gem to pay off his debts.

If you walked into this one expecting another Sandler comedy, you’re sorely mistaken… Ratner, a jeweler himself, understands the value of this gem and struggles to balance his messy personal life (which is quickly falling apart) with his quest. The film, which is certainly more a crime thriller than a comedy, explores high concepts for Sandler including gambling, infidelity, greed, and includes lots of violence.

Uncut Gems garnered much critical acclaim, and many have considered Sandler’s leading role as his greatest performance on screen.

3. Happy Gilmore (1996)

The second half to Adam Sandler’s original success, Happy Gilmore came out only a year after Billy Madison and follows the titular character who switches careers from ice hockey to golf after discovering his newfound talents. Gilmore quickly learns that his grandma owes the IRS an obscene amount of money, causing him to play to pay it off.

The film marks director Dennis Dugan’s first collaboration with Sandler (who he would work with again numerous times) and features one of the greatest golf rivalries in film between Happy and pro-golfer Shooter McGavin (Christopher McDonald, The Iron Giant). Happy’s coach and mentor, Chubbs Peterson (Carl Weathers, Rocky), is also a wonderful addition who helps Happy achieve his true potential.

Happy Gilmore is an Adam Sandler classic that is as beloved today as it was then because of Sandler’s own charm, not to mention his lack of golf etiquette.

4. The Wedding Singer (1998)

This Adam Sandler/Drew Barrymore (Never Been Kissed) 90s classic takes us back to the 80s where we join a wedding singer named Robbie Hart (Sandler) who falls in love with a waitress named Julia (Barrymore). The film has been adapted into a musical and actually crossed over with The Goldbergs in the episode of the same name.

Between the crazy love triangle involving Robbie, Julia, and Glenn (Matthew Glave, Stargate SG-1), Sandler’s continual mental breakdown, and cameos from Billy Idol and Steve Buscemi, there’s a lot to love here. If you haven’t checked this one out yet, put it on your list immediately!

The Wedding Singer is often considered one of Sandler’s best comedies, known for being just as much a rom as it is a com, so be sure to make a date night out of it!

5. Big Daddy (1999)

Sandler’s highest-grossing film domestically until Hotel Transylvania 2 in 2015, Big Daddy follows Sonny Koufax (Sandler), who, after being dumped by his girlfriend, decides to show her how responsible he is by adopting a five-year-old boy (Dylan and Cole Sprouse, The Suite Life of Zack & Cody) who shows up randomly on his doorstep.

This father-son comedy will make you both laugh and cry as you watch Sandler learn the hard way about what it means to be a single dad. Dylan and Cole Sprouse’s role as Julian helped shove the future Disney Channel stars into the spotlight after they won the hearts of Sandler and his audience everywhere.

Big Daddy was an instant classic when it premiered and still remains one of Sandler’s best and most heartwarming stories to date. 

6. 50 First Dates (2004)

Another Sandler/Barrymore rom-com, 50 First Dates is this writer’s favorite Sandler comedy, with lots of laughs (and drama) for just about everyone involved. The story, set in Hawaii, follows Henry Roth (Sandler), a marine vet who falls in love with Lucy (Barrymore), a girl who has short-term memory loss and forgets him every day.

What makes 50 First Dates so memorable is its unique concept and flawless execution. The chemistry between Sandler and Barrymore (which we have seen before) is electric, and Sandler’s own antics make him pretty loveable. Plus, Sean Astin (The Lord of the Rings), Rob Schneider (Benchwarmers), and Dan Akroyd (Ghostbusters) make for some great co-stars.

50 First Dates is one of Sandler’s most beloved films for a reason, and it’s because it proves that sometimes we have to go to extremes for true love.

7. Click (2006)

If you remember seeing the commercials for Click back in the day, then you probably thought it would be super cool to have your own “universal remote” that could control time. Michael Newman (Sandler) finds out the hard way that being able to skip around in your life isn’t exactly all it’s cracked up to be.

If the premise feels sort of like the Nicholas Cage-led film The Family Man (which is also a must-watch), then it’s because ultimately Click is sending the same message: put your family first. Sandler’s character, Michael, learns this the hard way so that we don’t have to. The film also stars Kate Beckinsale (Underworld) as Michael’s wife Donna and Christopher Walken (The Prophecy) as the eccentric inventor Morty. 

Click plays like a cautionary tale to be thankful for the time you have with your family. Maybe you could spend more of that time watching Adam Sandler movies together? 

8. Punch-Drunk Love (2002)

If you never thought that Adam Sandler would work with an auteur filmmaker like Paul Thomas Anderson (There Will Be Blood), then look no further than the romantic comedy-drama Punch-Drunk Love. This one follows the anxious entrepreneur Barry (Sandler) as he falls in love with his sister’s co-worker Lena (Emily Watson, Chernobyl).

If that sounds too boring to you, then don’t worry. Throughout the film, Barry is pursued by four phone sex line henchmen (yes, really), who do their best to extort money from him. To make matters worse, their boss is Philip Seymour Hoffman (Mission: Impossible III) who plays a mattress salesman. Sandler and Watson’s chemistry is ecstatic, making you hope that they’ll find their happy ending.

Punch-Drunk Love is a wild ride that takes you across the globe on an adventure that is worth risking everything for. It’s pretty entertaining too.

9. The Waterboy (1998)

One of the most famous sports comedies out there, The Waterboy follows Adam Sandler as Bobby Boucher, Jr., a somewhat mentally challenged 31-year-old who serves as the water boy to his college football team. In an almost Rudy-like fashion, Bobby overcomes the odds and begins to play football, date, and take back his life.

Joining Sandler on this adrenaline-fueled ride is Kathy Bates (Misery) as Bobby’s emotionally abusive and controlling “Mama” Boucher, Henry Winkler (Happy Days) as Coach Klein, and Fairuza Balk (Paradise City) as Bobby’s girlfriend Vicki. There’s a lot to love about Bobby Boucher Jr., but nothing beats his solid determination and growing love for the game.

The Waterboy is a great feel-good sports dramedy that will make you believe you can accomplish anything. Because if Adam Sandler can do it, why can’t you?

10. Funny People (2009)

A Judd Apatow (The 40-Year Old Virgin) psychological comedy-drama, Funny People is about a dying (and retired) comedian (Sandler) as he attempts to fix his relationship with his now-married ex-fiancee (Leslie Mann, Knocked Up) while also mentoring an aspiring comedian (Seth Rogan, Freaks and Geeks).

This film gets a little crazy, and Sandler’s all-too-familiar antics are often hard to swallow, but Funny People is an excellent look at failing to learn from your mistakes but still getting back up to try again. George Simmons, like many of Sandler’s characters, just seems to be Sandler in a “what if” scenario where he is dying and wants to fix his life before he goes.

Funny People, despite the heavy themes, is a good time, with lots of laughs and plenty of heart.