Adam Sandler’s 9 Best Movies Before He Lost His Mojo

Adam Sandler is one of Hollywood’s most polarizing movie stars, with his films consistently dividing audiences and critics. While reviewers often dub his comedy style as low-brow and obnoxious, many of even his worst-received flicks have still gone on to earn big at the box office. Lately though, his appeal has seemed to run out, with several of his recent films becoming commercial disappointments.

Even his deal with Netflix, while lucrative, hasn’t exactly helped his reputation rebound. All of his original films for the streamers have earned dismal reviews from the critics. But there was a time when Sandler made movies that people actually liked. Here’s look back at nine of the actor’s best roles before he lost his mojo.

1. Happy Gilmore

Source: Universal Pictures
Happy Gilmore | Universal Pictures

The 1996 comedy stars Sandler as a rejected hockey player who takes up professional golf in order to save his grandma’s house from getting seized by the IRS. It’s a low-brow comedy to be sure, but most of its gags actually stick the landing, instead of falling with a massive thud.

As is par for the course with Sandler movies, not all critics got it (with the movie holding a 60% rating on Rotten Tomatoes). But for the comic’s remaining fans, it remains a favorite.

2. The Wedding Singer

Source: New Line Cinema
The Wedding Singer | New Line Cinema

OK, so it might be cheesy, but The Wedding Singer is also sweet, charming, and filled with genuinely funny moments. The 1998 rom-com stars Sandler as singer Robbie Hart, who goes on a quest to save his crush from marrying her terrible fiancé.

Even with its hokey parts, you can’t help but root for the characters and it’s one of the few Sandler comedies in which the actor goes for more than just the obvious laughs. The first of several collaborations between Sandler and Drew Barrymore, The Wedding Singer is easily one of the actor’s most well-regarded films to date.

3. Billy Madison

Source: Universal Studios
Billy Madison | Universal Studios

The 1995 film is the ideal vehicle for Sandler’s infantile humor. It stars the actor as an overgrown wealthy slacker, who spends his days drinking by the pool – until his dad forces him to go back to school so he can take over the company.

The film is pretty absurd, but as long as you accept that, the laughs come quickly and often. With some of the most quotable lines in comedy film history to boot, it’s no wonder why the movie, while not exactly critically appraised, has since become a cult favorite.  

 4. Funny People

Source: Columbia Pictures
Funny People | Columbia Pictures

While Sandler doesn’t show off his dramatic acting chops often, this 2009 dramedy proves he has them. The Judd Apatow flick features Sandler as a comedic movie star, who is forced to reevaluate his life after he learns he has a potentially deadly blood disease.

The movie garnered fairly positive reviews and Sandler, in a rare occurrence, was credited for elevating it with his performance. As Rolling Stone wrote, “Sandler, relaxed, focused, alert to nuance, plays George, and it’s his best performance ever (right up there with Punch-Drunk Love).” Despite being one of Sandler’s best-reviewed works, the film ended up being a box office disappointment.

5. Punch-Drunk Love

Source: Columbia Pictures
Punch-Drunk Love | Columbia Pictures

The 2002 flick is another example of a darker Sandler movie that earned a positive critical response, but ended up tanking at the box office. The romantic comedy-drama stars Sandler as a lonely and socially impaired small business owner who falls in love with his sister’s co-worker, only to have the romance threatened by an extortionist.

Sander’s touching portrayal earned him some of the best reviews of his career, as well as a Golden Globe nod for Best Actor in a Comedy.

6. Big Daddy

Source: Columbia Pictures
Big Daddy | Columbia Pictures

The 1998 film features Sandler in a familiar role, as a perpetually immature adult who simply refuses to grow up. This time around though, his character takes in a child in order to show his girlfriend he’s ready for commitment.

While the movie was critically panned, it is definitely one of Sandler’s more fun and successful efforts. After all, who can resist watching a cute kid get to live out his fantasies – from pigging out on junk food to tripping a rollerblader in the park?

7. Reign Over Me

Source: Columbia Pictures
Reign Over Me | Columbia Pictures

A movie about a man who loses his family in the Sept. 11th attacks and is still struggling to recover from his grief doesn’t exactly scream Sandler. But the actor’s portrayal in the 2007 film is surprisingly affecting.

The project, co-starring Don Cheadle, earned mostly favorable reviews, with critics calling Sandler’s performance “poignant,” “amazing,” and “a triumph.”

8. The Waterboy

Source: Buena Vista Pictures
The Waterboy | Buena Vista Pictures

The 1998 sports comedy stars Sandler as a waterboy for a college football team, who discovers he has a unique tackling ability and eventually becomes a member of the team. Filled with blunt and crude humor, the movie isn’t one for the critics, but purely for Sandler’s fans.

You won’t find any sophisticated comedy here, but you will find some sincerely endearing and entertaining moments that have helped solidify this project as one of the actor’s most memorable films yet.

9. Hotel Transylvania

Source: Columbia Pictures
Hotel Transylvania | Columbia Pictures

Sandler lends his voice to the character of Dracula in this 2012 animated comedy, which takes place in a titular lavish five-stake resort, where monsters and their families can live it up without human interference. In the film, Dracula is an aging father who has a hard time dealing with his daughter growing up.

The actor brings a light charm to Dracula, which makes the character easy to root for. Sandle reprised his role in the sequel, Hotel Transylvania 2 this year.

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