5 Best Adam Sandler Movies, Ranked by Rotten Tomatoes Score

Former Saturday Night Live cast member Adam Sandler has been headlining movies since he left the show in 1995.

However, Sandler’s low-brow comedies have dominated his career and occasionally stifled his acting talent.

With Sandler’s Happy Gilmore 2 now streaming on Netflix, Watch With Us has rounded up the five best Adam Sandler movies ranked by Rotten Tomatoes score.

Only two of our selections qualify as traditional Sandler comedies. The remaining three demonstrate that Sandler has enough dramatic chops to be worthy of an Oscar someday.

5. ‘Happy Gilmore’ (1996)

Rotten Tomatoes rank: 62 percent

The title character of Happy Gilmore is a golfer with a hockey mentality. Happy (Sandler) never saw a future for himself off the ice after he failed to become a pro hockey player. But under the tutelage of  Derick “Chubbs” Peterson (Carl Weathers), Happy learns just enough about golf to enter the PGA tour and potentially save his grandmother’s home from foreclosure.

Happy has a knack for rubbing people the wrong way, including his tour rival Shooter McGavin (Christopher McDonald). Since Shooter is eager to force Happy out of the sport, he devises numerous schemes to humiliate him. But it’s going to take more than mean hecklers for Happy Gilmore to go down.

Happy Gilmore is streaming on Netflix.

4. ‘The Wedding Singer’ (1998)

Rotten Tomatoes rank: 72 percent

The Wedding Singer rolls the clock back to 1985 as Sandler steps into the title role as Robbie Hart. Robbie used to have ambitions of performing for real crowds instead of for weddings, and that’s why his fiancée, Linda (Angela Featherstone), has fallen out of love with him and dumped him at the altar.

On the rebound, Robbie starts falling hard for Julia Sullivan (Drew Barrymore), a waitress who has every quality he wants from a woman — except her relationship status. Julia is already planning to marry Glenn Gulia (Matthew Glave), and he wants to do everything he can to keep Robbie and Julia from getting together. Will he be luckier in love the second time around?

The Wedding Singer is streaming on Tubi.

3. ‘Punch-Drunk Love’ (2002)

Rotten Tomatoes rank: 79 percent

For a long time, Punch-Drunk Love was unquestionably Sandler’s best movie. Director Paul Thomas Anderson gave the actor a chance to show he could do more than lowbrow comedy, and Sandler ran with it. He even gives an emotionally affecting performance as Barry Egan, a very lonely man suffering from anxiety and rage issues.

Lena Leonard (Emily Watson), a coworker of one of Barry’s sisters, goes out of her way to meet him and pursue a relationship. Barry seems eager to see where things lead with Lena, but he’s got some family drama and a harassment campaign against him that he needs to address first.

Punch-Drunk Love is streaming on Hoopla.

2. ‘Uncut Gems’ (2019)

Rotten Tomatoes rank: 91 percent

Sandler took another dive into drama in Uncut Gems for what may be the best performance of his career. Sandler plays Howard Ratner, a successful jeweler who has enough money to support his wife, Dinah (Idina Menzel), and his mistress, Julia De Fiore (Julia Fox).

Howard also has an excessive gambling problem that may cost him everything he has. To get back into the black, Howard is betting that an opal diamond can turn his life around if he sells it at an auction. That’s assuming that Howard can get the opal back from NBA player Kevin Garnett, who doesn’t show any inclination to return it.

Uncut Gems is available to buy or rent on Prime Video.

1. ‘Hustle’ (2022)

Rotten Tomatoes rank: 94 percent

Sandler’s best film, Hustle, has an even larger NBA presence than Uncut Gems. This time, Sandler plays Stanley Sugerman, a scout for the Philadelphia 76ers whose job is keeping him from being with his wife, Teresa (Queen Latifah), and their daughter, Alex (Jordan Hall).

When he finds an undrafted superstar, Bo Cruz (Juancho Hernangómez), in Spain, Stanley is over the moon. If Stanley can get Bo into the NBA, it will vindicate every decision that Stanley has made and potentially secure him a coaching job with the 76ers. But that proves to be very difficult thanks to Bo’s rivalry with Kermit Wiltis (Anthony Edwards), a player who doesn’t want him to make the NBA.

Hustle is streaming on Netflix.