No film has been more important for Adam Sandler’s career than Happy Gilmore. The 1996 classic, released on February 16th, was an immediate smash hit. It’s had long-lasting cultural relevance, too. From endless quotes to a 2025 sequel, everyone is familiar with the movie, even if they’ve never actually seen it. In the process, the film helped catapult Sandler from talented Saturday Night Live cast member to full-blown movie star.
Three decades later, where does Happy Gilmore rank among the Sand Man’s best movies? On this 30th anniversary, let’s look back at the five best Sandler films.
Honorable Mentions
- Anger Management
- Airheads
- Big Daddy
- Mr. Deeds
- The Waterboy
5. Billy Madison
Although Happy Gilmore took Sandler’s career to new heights, Billy Madison was his first true breakout role. It’s the story of a wealthy man-child forced by his father to re-take grades 1 through 12 in order to gain an inheritance. Absurd premise? Of course, but that’s sort of the point. There’s something about a ‘put your mind on hold’ comedy that is comforting.
Like it or not, Sandler has made his biggest mark with absurd, slightly immature comedies. In many ways, Billy Madison sets the template for many of his later flicks. This is one that most detractors of the comedian’s work will avoid. However, it’s grown into one of his more beloved films among fans. The titular character of Billy is unforgettable, as well. It’s divisive, but this 1995 feature is essential viewing among Sandler’s early work.
4. The Wedding Singer
Now, a more sentimental side of Sandler. The Wedding Singer, set in 1985, tells the story of a wedding singer (duh) who falls in love with a waitress (Drew Barrymore). Timing helps this 1998 classic; the general public hadn’t been overwhelmed with endless 80’s nostalgia at this point.
Is this one too saccharine? Maybe to some, but with a title like that, romance is to be expected. Following a string of laugh out loud comedies, The Wedding Singer showed that Sandler had some range. I doubt he lands some of his later, more ‘serious’ roles without having starred here. It’s also the actor’s first time sharing the screen with Barrymore, a frequent collaborator. An important, feel-good comedy with long-lasting impact? It’d be difficult for this one not to make the list.
3. Uncut Gems
Before Marty Supreme, there was Uncut Gems. In many ways, this 2019 film has sparked a late-career renaissance. This high-stakes drama from the Safdie brothers is nothing short of anxiety-inducing. While that drove away some viewers, most couldn’t look away. Without Sandler at the wheel, it all could have easily gone sideways.
Howard ‘Howie’ Ratner is a character unlike any other. The jeweler places some bad bets with the wrong crowd, leading to a frenetic scramble involving mobsters, family members, Kevin Garnett and Mike Francesa(!). This all climaxes with a truly unforgettable finale. Laugh out loud, this film is not (although it does have some comedic moments). Still, this is sure to be a major piece of Sandler’s legacy going forward.
2. Happy Gilmore
At last, we get to the one that inspired this list. As previously mentioned, Happy Gilmore was a star vehicle for Sandler. He’s able to toe the line between chaotic, abrasive, and rootable. The end result is Happy, a protagonist that you can’t help but pull for. It helps that he’s partnered with some truly unforgettable supporting characters. The late Carl Weathers is terrific as Chubbs, while Christoper McDonald steals the show as Shooter McGavin.
It’s a great premise on paper. What if a hockey goon took his slap shot to the PGA? Seeing the physical, intense Gilmore clash with the polite society world of professional golf never gets old. I mean, just look at how quotable this thing is. Even if you’ve never watched the 1996 classic, chances are you’ve heard someone say “Just tap it in!” or “The price is wrong!”. If you had to show an alien any Sandler picture, the choice is obvious.
1. Punch-Drunk Love
Full disclaimer: I don’t think this is the most ‘Adam Sandler’ of Adam Sandler movies. That’s not taking anything away from his performance, which is truly spectacular. However, Punch Drunk Love feels like a more comedic showing from acclaimed director Paul Thomas Anderson. Regardless, the end result is a funny, touching feature from one of Hollywood’s best filmmakers.
About that Sandler performance: he’s so good here. It would have been easy to make Barry Egan into a punching bag (no pun intended). Instead, this portrayal makes you feel for the guy, a hopeless, slightly unstable romantic searching for companionship. Great supporting performances from Emily Watson and the great Phillip Seymour Hoffman help as well. In addition, the 95-minute runtime absolutely flies by. For the ideal combination of enjoyable, engaging, and moving, this is the top Sandler film.
