My Top 5 Adam Sandler Movies: A Tough but Fun Selection
Crafting this top 5 list of Adam Sandler movies was no easy feat. As a lifelong fan of his work, narrowing down my favorites felt like choosing between cherished memories. I could easily expand this to a top 20, as the list of Adam Sandler movies I adore far outweighs those I don’t. That said, I’m sticking to my self-imposed top 5 rule, even though I anticipate some spirited debates in the comments. Your number one might not even make my list, and my top pick might surprise you. Adam Sandler ranks among my top three favorite actors, and his unique blend of humor, heart, and relatability shines through in every role. I considered listing my other favorite actors here, but I’ll save that for another top 5 blog post—stay tuned!
1. Billy Madison (1995)
“You ain’t cool unless you pee your pants!” This iconic line encapsulates the absurd, quotable brilliance of Billy Madison. The premise is delightfully simple: a grown man, Billy Madison (Sandler), must repeat grades 1 through 12 to prove he’s worthy of inheriting his father’s multimillion-dollar company. Sandler’s childlike energy and knack for physical comedy make this early role a perfect showcase of his comedic roots. From the dodgeball scene to his rivalry with Eric (Bradley Whitford), every moment is packed with hilarity and heart. This movie remains a timeless classic that I revisit regularly, and it never fails to make me laugh.
2. Happy Gilmore (1996)
What happens when you combine Adam Sandler’s chaotic energy with the genteel sport of golf? You get Happy Gilmore, a comedy that’s as outrageous as it is unforgettable. Sandler plays Happy, a failed hockey player turned golfer, whose unorthodox style shakes up the PGA tour. The movie’s humor peaks in moments like Chubbs (Carl Weathers) losing his wooden hand to an alligator or the legendary brawl with Bob Barker (“The price is wrong!”). Sandler’s chemistry with co-stars like Julie Bowen and Christopher McDonald elevates this sports comedy to iconic status. It’s a hole-in-one for fans of Sandler’s slapstick brilliance.
3. The Waterboy (1998)
The Waterboy holds a special place in my heart as the first Adam Sandler movie I ever watched. As a kid, I must have seen it close to 100 times, and it still feels as fresh as ever. Sandler’s portrayal of Bobby Boucher, a socially awkward waterboy turned football star, is both hilarious and endearing. The film’s Southern charm, memorable characters (hello, Mama Boucher!), and absurd humor make it a standout. Plus, it’s the only reason most of us know the term “medulla oblongata.” This childhood classic is a testament to Sandler’s ability to create lovable underdog characters.
4. The Longest Yard (2005)
Yes, The Longest Yard is a remake, but Sandler’s take on this 1974 classic is one of the best remakes in cinematic history. Playing Paul “Wrecking” Crewe, a disgraced quarterback leading a team of prison inmates against the guards, Sandler brings his signature humor and surprising depth to the role. The sports theme resonates with me, as my love for athletics mirrors Sandler’s own passion, which shines through in his performance. The ensemble cast, including Chris Rock, Burt Reynolds, and James Cromwell, adds layers of humor and heart. This movie proves Sandler can balance comedy with grit.
5. Eight Crazy Nights (2002)
Eight Crazy Nights is an underrated gem in Sandler’s filmography. This animated, musical holiday movie follows Davey Stone, a troubled loner who finds redemption during Hanukkah. Sandler’s voice acting, combined with catchy songs like “Technical Foul,” brings a unique flavor to this heartfelt comedy. It’s goofy, irreverent, and packed with holiday spirit, making it a perfect watch for the season. If you haven’t seen it yet, consider this your technical foul—stream it ASAP! This film showcases Sandler’s versatility, blending his comedic roots with a touch of emotional depth.
Why Adam Sandler Movies Resonate
What makes Adam Sandler’s films so special? For me, it’s his ability to create characters that are flawed, relatable, and ultimately redeemable. His sports-related comedies, like Happy Gilmore and The Longest Yard, stand out because they tap into his genuine love for athletics, which adds authenticity to the roles. Even his “lesser” films, like Jack and Jill or Grown Ups 2, have a charm that keeps me entertained. I’m hard-pressed to name an Adam Sandler movie I dislike—his worst still outshines many other comedies.
Honorable Mentions
The list of Sandler movies that almost made the cut is long. Here are a few that could easily swap into the top 5 on any given day:
Big Daddy (1999): Sandler as a slacker-turned-father figure is both hilarious and touching.
50 First Dates (2004): A romantic comedy with heart, thanks to Sandler’s chemistry with Drew Barrymore.
Grown Ups (2010): A nostalgic ensemble comedy that captures lifelong friendships.
Click (2006): A surprisingly emotional blend of comedy and life lessons.
That’s My Boy (2012): An over-the-top guilty pleasure with Andy Samberg.
Anger Management (2003): Sandler and Jack Nicholson make for an unforgettable duo.
Mr. Deeds (2002): A charming remake with Sandler’s signature underdog vibe.
Let’s Hear From You!
I’m curious: what are your favorite Adam Sandler movies? Are there any you can’t stand? I struggle to find a Sandler film I don’t enjoy, but I’d love to hear your thoughts. Drop your top 5 in the comments, and let’s see how much we agree (or disagree)! Also, keep an eye out for my next top 5 blog, where I’ll rank my favorite actors. Spoiler: Sandler’s already secured a spot.
