Every Adam Sandler Movie, Ranked Best To Worst By Fans (2024)

Happy Gilmore is a cult classic that blends sports, comedy, and a touch of heart in a way only Adam Sandler can. In this hilarious tale, Sandler stars as Happy Gilmore, a failed hockey player who discovers a unique talent for golf. His unconventional approach brings chaos to the serene game, especially when he clashes with the arrogant pro Shooter McGavin. The film co-stars Christopher McDonald as McGavin and Julie Bowen as the love interest, Virginia Venit. Upon its release in 1996, Happy Gilmore received mixed reviews from critics but was a hit with audiences, quickly becoming a beloved staple of '90s comedy. Its memorable one-liners and outrageous scenes have ensured its status as a fan favorite, enduring in popularity years after its release.

Billy Madison is a quintessential Adam Sandler comedy that has firmly embedded itself in the hearts of his fans. Sandler plays the titular character, a carefree and immature heir to a hotel fortune, who must go back to school to prove his worthiness to run the family business. From kindergarten to high school, Billy's hilarious and heartwarming journey to adulthood is filled with absurd challenges and laugh-out-loud moments. The film co-stars Bridgette Wilson as the love interest Veronica Vaughn, and Darren McGavin as Billy's disapproving father. Released in 1995, Billy Madison garnered mixed critical reviews but was an instant hit with audiences, solidifying Sandler's status as a comedy superstar and spawning countless quotes that remain popular in pop culture lexicon.

The Waterboy is one of Adam Sandler's most endearing and successful comedies, where he stars as Bobby Boucher, a socially awkward waterboy for a college football team who discovers his unique talent for tackling. This leads him from the sidelines to becoming the team's most valuable player. The film features a standout performance by Kathy Bates as Bobby's overprotective mother, with Henry Winkler as the kindly Coach Klein, who gives Bobby his chance. Since its release in 1998, The Waterboy struck a chord with audiences for its heartwarming underdog story peppered with Sandler's signature comedic style. Critics gave it mixed reviews, but it was a box office hit, further cementing Sandler’s place in the comedy zeitgeist with its memorable lines and scenes.

Big Daddy marks another hit in Adam Sandler's repertoire, showcasing a softer side of the comedian that resonated well with audiences. In the film, Sandler plays Sonny Koufax, a lazy law school grad who adopts a five-year-old boy to impress his girlfriend, only to learn valuable lessons about responsibility and love. The film coasts on the charming dynamic between Sandler and the young actor Cole Sprouse, who plays the adorable Julian. Released in 1999, Big Daddy received mixed reviews from critics who were divided on its sentimental approach versus Sandler's typical slapstick humor. However, the film was a box office success, appealing to a wide audience for its heartwarming storyline and proving Sandler's ability to pull at the heartstrings while delivering laughs.

50 First Dates is a heartwarming blend of comedy and romance that deviates from Adam Sandler's usual comedic style. Sandler stars as Henry Roth, a veterinarian living in Hawaii, who falls for Lucy Whitmore, played by Drew Barrymore. The twist? Lucy suffers from short-term memory loss, forgetting him the next day. The movie follows Henry's attempts to make Lucy fall in love with him every single day. Released in 2004, the film was praised for the undeniable chemistry between Sandler and Barrymore, echoing their success in The Wedding Singer. Critics gave it mixed reviews, appreciating its sweet nature but questioning its comedic elements. Despite this, 50 First Dates was a box office hit, cherished for its unique love story and became one of the most memorable romantic comedies of the 2000s.

The Wedding Singer is a beloved rom-com that stands out in Adam Sandler's filmography, thanks to its engaging mix of humor, heart, and 80s nostalgia. Sandler shines as Robbie Hart, a wedding singer with a broken heart, who finds a kindred spirit in Julia Sullivan, portrayed by Drew Barrymore, a waitress engaged to the wrong guy. Set against the vibrant backdrop of the 1980s, their budding romance is both sweet and hilariously quirky. Released in 1998, the film received positive reviews for its charming leads and the palpable chemistry between Sandler and Barrymore. Praised for its clever use of 80s music and culture, The Wedding Singer was not only a box office success but also solidified its place as a feel-good classic, beloved by fans and critics alike.