Adam Sandler has had quite a career in Hollywood. Although his films might not have the power they once did, he was a dominant force throughout much of the ’90s and early 2000s.

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While he primarily made a name for himself as a comedic actor,  Sandler quickly expanded his filmography to include some dramatic roles as well; some of which managed to become instant classics that remain fan favorites to this day.

10) Click (2006)

Michael Newman (Adam Sandler) and Morty (Christopher Walken) relive a memory from the past in Click (2006) via Columbia Pictures

Sometimes all a movie needs is a great premise, and Sandler’s Click does exactly that; presenting audiences with a plot wherein a remote control that actually has the ability to control reality itself.

Adam Sandler gave a decent enough performance, but the movie’s true heart was what it said about humanity, life, and the family people love along the way. It had a sad and twist ending that wrapped it up quite nicely.

9) Bedtime Stories (2008)

Skeeter Bronson (Adam Sandler) tells a bedtime story to his niece Bobbi (Laura Ann Kesling) and nephew Patrick (Jonathan Morgan Heit) in Bedtime Stories (2008) via Walt Disney Pictures

Bedtime Stories was a cute family film about a hotel worker trying to take over his family business. However, the story was wrapped in a interesting framework involving two children and Adam Sandler telling them bedtime stories.

As he told the stories, though, those very events started to happen in the outside world. It made for a magical film that was a refreshing story compared to some of Sandler’s rather raunchier work.

8) 50 First Dates (2004)

Henry Roth (Adam Sandler) fakes being kidnapped to meet Lucy Whitmore (Drew Barrymore) in 50 First Dates (2004) via Columbia Pictures

Although Adam Sandler’s movies certainly have romantic subplots, they aren’t strictly romantic comedies. 50 First Dates is an exception to that rule as it had a very adorable premise.

Drew Barrymore stars as a woman that suffers from short-term memory loss. Unaware of this fact, Adam Sandler’s character falls in love with her and becomes determined to build a life with her. The film has a lot of ups and downs as the couple try to make their life work, leading up to a very sweet ending.

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7) Eight Crazy Nights (2002)

Davey Stone (Adam Sandler) is sentenced to community service in Eight Crazy Nights (2002) via Columbia Pictures

There are just so many Christmas movies that sometimes it’s hard to think of movies that are about Hanukkah. Adam Sandler’s animated film, Eight Crazy Nights, is one of them.

Even though it’s animated, it’s hard not to notice Adam Sandler as the main character. He plays an alcoholic troublemaker that has a hard time getting along with his family. It’s a pretty sweet movie for if no other reason than it features a holiday that doesn’t get as much screen time as its Christian counterpart.

6) Reign Over Me (2007)

Charlie Fineman (Adam Sandler) reconnects with former roommate Alan Johnson (Don Cheadle) in Reign Over Me (2007) via Columbia Pictures

Reign Over Me might be one of the first films to use 9/11 as a character’s foundation. Ditching his usual comedy, Sandler plays a grief-stricken man unable to move on with his life after his wife and son are killed in the tragic event.

Don Cheadle’s character, a former roommate, tries to help Sandler’s troubled character find some sense of normalcy through his despair. It’s a heart-breaking movie to watch as both actors do a phenomenal job conveying their emotions in their respective roles.

5) The Waterboy (1998)

Bobby Boucher (Adam Sandler) channels his tackling fuel in The Waterboy (1998) via Touchstone Pictures

If there’s one thing Adam Sandler knows it’s creating memorable characters. The Waterboy is about a goofy man in backcountry Louisiana that loves being a college football waterboy. 

However, his life takes a turn when the coach of a terrible college football team realizes the waterboy is an incredible tackler. The film is filled with ridiculous humor and one-liners that are still being referenced by fans decades later.

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4) The Wedding Singer (1998)

Robbie Hart (Adam Sandler) looking rough after being dumped by his fiancé Linda (Angela Featherstone) in The Wedding Singer (1998) via New Line Cinema

On the surface, The Wedding Singer really isn’t about anything. Adam Sandler plays a popular wedding singer in the 1980s that becomes love-stricken with Drew Barrymore’s character after his fiancé Linda dumps him at the altar.

However, the film definitely has a lot of heart and can definitely be classified as a romantic comedy. It also has a very sweet ending that is hard not to love as Sandler has to compete with a jerk for the girl.

3) Big Daddy (1999)

Sonny Koufax (Adam Sandler) has a heartfelt talk with Julian (Cole/Dylan Sprouse) in Big Daddy (1999) via Columbia Pictures

Big Daddy may just be Adam Sandler’s most heartfelt movie, mainly because it’s not about romance as much as it is about parenthood. Sandler plays a guy struggling to find his footing in life who suddenly becomes responsible for a child.

The movie is filled with tons of great typical Adam Sandler humor, but it also has one of the most profound arcs that any of this characters go through. Start to finish, Big Daddy is a cinematic triumph.

2) Happy Gilmore (1996)

Happy Gilmore (Adam Sandler) is being given a piece of advice by Gold legend Chubbs Peterson (Carl Weathers) in Happy Gilmore (1996) via Universal Pictures

Adam Sandler had back-to-back comedy classics in the ’90s. On of the first ones was Happy Gilmore, which sees a terrible hockey player take up golf to help his aging grandmother.

The film is jam-packed with iconic one-liners. Also, the clash and culture between hockey and golf creates a fertile ground for some great comedy. This doesn’t even take into account the movie’s memorable golfer villain played by Christopher McDonald, Shooter McGavin.

1) Billy Madison (1995)

Billy Madison (Adam Sandler) and his friends Jack (Mark Beltzman) and Frank (Norm MacDonald) leave a bag of poop in front of the house of Ted ‘Old Man’ Clemens (Jack Mather) in Billy Madison (1995) via Universal Pictures

Besides Saturday Night Live, Billy Madison was many people’s first introduction to Adam Sandler. He plays a rich heir to a hotel empire who goes back to school to prove to his father that he can take over the company.

The movie may be absolutely ridiculous without any strong characterization or themes, but that doesn’t take away from the fact that the film is simply hilarious. Billy Madison successfully put Adam Sandler on the map as a truly great comedic actor.

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