The Best and Worst of Adam Sandler

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Updated September 17, 2023 88.8K votes 5.7K voters 50.2K views
Over 5.7K Ranker voters have come together to rank this list of The Best and Worst of Adam Sandler
Voting Rules
Movies that star Adam Sandler
Latest additions: Murder Mystery 2
Most divisive: Funny People

Differentiating between the best Adam Sandler movies and the worst Adam Sandler movies can be a simple matter of taste (or lack thereof) which is completely subject to interpretation. No one is ever going to accuse Adam Sandler of having movies that rank in the best movies ever, but there are at least a few Adam Sandler movies that can be ranked with the funniest movies of all time, so perhaps it's best to focus there.

Many consider Adam Sandler to be an idiot genius (or idiot/genius...or just an idiot), but the guy makes some funny movies. Happy Gilmore and Billy Madison, which came right at the start of Sandler's film career, are comic legends. On the other side of the legend coin are movies like Jack & Jill. 

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  • Happy Gilmore
    1

    Happy Gilmore

    Adam Sandler, Christopher McDonald, Julie Bowen
    3,690 votes
    • Released: 1996
    • Directed by: Dennis Dugan
    In Happy Gilmore, the title character, played by Adam Sandler, is a failed hockey player with an uncanny talent for golf. His powerful swing, honed from years of hockey playing, propels him into the professional golfing scene. As he battles to win the championship against his arrogant rival Shooter McGavin (Christopher McDonald), Happy also fights to save his grandmother's house from foreclosure. This sports-comedy flick, directed by Dennis Dugan, presents an unconventional approach to golf and life, showcasing Sandler's knack for physical comedy amid heartfelt moments.

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  • Big Daddy
    2

    Big Daddy

    Adam Sandler, Joey Lauren Adams, Jon Stewart
    3,553 votes
    • Released: 1999
    • Directed by: Dennis Dugan
    In Big Daddy, a comedic journey unfolds as Sonny Koufax (Adam Sandler), an unmotivated bachelor, unexpectedly becomes the guardian of a five-year-old boy, Julian (Cole and Dylan Sprouse). The movie, bestowed with the Blockbuster Entertainment Award for Favorite Comedy, navigates through Sonny's haphazard attempts at parenting. As he stumbles and fumbles, he learns life-altering lessons in responsibility and love. This comedy-drama, directed by Dennis Dugan, captures the chaos and hilarity ensuing from an unprepared man's transition into fatherhood while maintaining its light-hearted charm throughout.

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  • The Waterboy
    3

    The Waterboy

    Adam Sandler, Kathy Bates, Henry Winkler
    3,612 votes
    • Released: 1998
    • Directed by: Frank Coraci
    In the comedy film, The Waterboy, Bobby Boucher (Adam Sandler), a socially awkward water boy for a college football team, discovers his unique tackling skills and becomes a member of the team. His domineering mother (Kathy Bates) disapproves of this new path, creating tension between them. His coach (Henry Winkler), on the other hand, sees potential in Bobby's talent and encourages him to pursue it. As Bobby navigates his newfound fame and personal life struggles, he transforms from an underdog into an unlikely hero.

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  • Billy Madison
    4

    Billy Madison

    Adam Sandler, Darren McGavin, Bridgette Wilson-Sampras
    3,625 votes
    • Released: 1995
    • Directed by: Tamra Davis
    Billy Madison is a comedy flick that showcases the life of Billy Madison, a man-child played by Adam Sandler. He's an heir to a hotel empire, but his father (Darren McGavin) doubts his capability to take over. Hence, he's forced to go back to school, starting from kindergarten up to high school, in order to prove his worthiness. The movie takes viewers through hilarious situations as Billy navigates the education system and tries to win over his teacher Veronica Vaughn (Bridgette Wilson). This film marked a significant point in Sandler's career and is noted for its humorous portrayal of adult immaturity with a unique twist on the redemption narrative.

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  • 50 First Dates
    5

    50 First Dates

    Adam Sandler, Drew Barrymore, Rob Schneider
    3,354 votes
    • Released: 2004
    • Directed by: Peter Segal
    In the romantic comedy 50 First Dates, marine veterinarian Henry Roth (Adam Sandler) lives an uncommitted life in Hawaii until he meets Lucy Whitmore (Drew Barrymore). Tragically, Lucy suffers from short-term memory loss, unable to remember anything from the day before. Undeterred, Henry, smitten and determined, has to win her heart anew each day. Directed by Peter Segal with a supporting cast including Rob Schneider and Sean Astin, this film is a humorous yet touching exploration of love's persistence against adversity. Despite its comedic tones, it subtly sheds light on the challenges of living with a cognitive disorder.

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  • The Longest Yard
    6

    The Longest Yard

    Adam Sandler, Chris Rock, Burt Reynolds
    2,960 votes
    • Released: 2005
    • Directed by: Peter Segal
    The Longest Yard, a blend of comedy and sports drama, unfolds as former NFL quarterback Paul Crewe (Adam Sandler) lands in prison. With Warden Hazen's (James Cromwell) insistence, he forms a team of inmates to challenge the guards in a high-stakes football game. Inmates like Caretaker (Chris Rock) and Switowski (Bob Sapp) become key players. The plot thickens with grueling training, underdog spirit, and surprising alliances. This 2005 remake of the 1974 classic, directed by Peter Segal, brings together an ensemble cast in an engaging tale of redemption and resilience on the gridiron.

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