Adam Sandler’s Classic Hits: Top 5 Comedy Films That Defined a Generation

Adam Sandler’s Classic Hits: Top 5 Comedy Films That Defined a Generation

Adam Sandler may have had his fair share of ups and downs, but his legacy in comedy was solidified during the late ’90s, when he churned out hit after hit that became instant classics. These films filled with goofy characters, over-the-top antics, and endlessly quotable lines made him the undisputed king of comedy for a generation. Sure, our parents may have rolled their eyes, but kids, teens, and young adults laughed until they cried, watching these movies on repeat. While Sandler's appeal seemed to wane in the 2000s as his angry, ridiculous characters became harder to digest (Jack and Jill, That's My Boy), he’s recently had a resurgence. With Netflix deals and some surprisingly strong performances in serious roles (Uncut Gems, Spaceman), Sandler has proved he’s more versatile than people thought. But there’s no denying that comedy is what he’s best known for and loves most. Here’s a look back at five of his all-time greatest comedy classics.

1. Happy Gilmore (1996)

Happy Gilmore isn’t just a funny movie; it’s a masterclass in Sandler’s brand of ridiculous, lovable aggression. Sandler stars as Happy, a failed hockey player who discovers an unexpected talent for golf. From his wild swings on the green to his epic brawls with Bob Barker, this film embodies Sandler's knack for blending slapstick with genuine heart. Happy is a hot-headed underdog you can’t help but root for, and the film’s bizarre mix of golf and hockey makes for some of the funniest sports scenes in movie history. If you've ever yelled "the price is wrong!" in a moment of frustration, you have Happy Gilmore to thank.

2. Billy Madison (1995)

In Billy Madison, Sandler plays the spoiled man-child Billy, who must redo grades 1 through 12 to inherit his father’s company. It’s pure, unfiltered Sandler chaos, from silly songs to a penguin hallucination that’s hard to forget. The humor is absurd, juvenile, and downright silly, but that’s exactly what made it a hit with younger audiences. Sandler’s portrayal of a grown man trying to navigate elementary school was fresh and outlandish, and it’s packed with quotable lines. Sure, the premise is a bit out there, but Sandler’s infectious energy and unapologetically goofy antics make it one of his most memorable roles.

3. The Wedding Singer (1998)

The Wedding Singer shows Sandler at his most charming, proving he’s not just a caricature but a lovable leading man. Set in the ’80s (with all the big hair and neon to prove it), Sandler plays Robbie, a wedding singer left heartbroken at the altar who finds himself falling for Julia (Drew Barrymore). Sandler and Barrymore have undeniable chemistry, making this romantic comedy an instant favorite. This film is different from his other hits because it mixes genuine sweetness with humor, giving Sandler a chance to play a character who’s goofy but also tender and relatable. Plus, the soundtrack is a nostalgic treat for anyone who loves ’80s music.

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4. Big Daddy (1999)

In Big Daddy, Sandler plays Sonny, a man with questionable maturity who decides to adopt a young boy to impress his ex-girlfriend. But what starts as a half-baked plan turns into a heartfelt story about fatherhood. Big Daddy balances Sandler’s crude humor with a surprisingly touching narrative, making it one of his most beloved comedies. Watching Sonny’s unconventional approach to parenting—from letting his kid dress however he wants to teaching him to handle bullies—is both funny and endearing. It’s a film that shows Sandler’s softer side without losing the laughs, proving that beneath the goofy exterior, there’s a lot of heart.

5. The Waterboy (1998)

The Waterboy may be one of Sandler's silliest films, but it's also one of his most iconic. As Bobby Boucher, a socially awkward water boy who unexpectedly becomes a football star, Sandler fully embraces the character’s eccentricity—complete with a thick Cajun accent. The film is ridiculous from start to finish, but Sandler’s commitment to Bobby’s oddball innocence makes it undeniably entertaining. With the support of legends Henry Winkler and Kathy Bates, this is a movie you’ll find yourself quoting for years to come. The Waterboy captures Sandler at his unfiltered best: it's over-the-top, absurd, and laugh-out-loud funny, even if you can’t help but groan at just how silly it all is.

Adam Sandler’s comedies from the ’90s weren’t just films; they were cultural events, shaping a generation’s sense of humour with absurd scenarios and unforgettable characters. While his career has had its ups and downs, these classics remind us why we fell in love with Sandler’s unique blend of humour in the first place. Whether he's angrily swinging a golf club, repeating first grade, or charming us at a wedding, Sandler's comedic magic is undeniable. Here’s hoping his recent resurgence brings back a bit of that original charm.