The release of Happy Gilmore 2 marked a significant milestone in Adam Sandler’s career, making this the ideal time to revisit other Adam Sandler must-watch movies. Since the original 1996 Happy Gilmore is widely celebrated as one of Sandler’s funniest films, the sequel’s success has reignited enthusiasm for his extensive filmography.
Although Adam Sandler’s comedies often receive mixed reviews, Happy Gilmore 2 has garnered surprisingly positive responses, holding a 63% score on Rotten Tomatoes and breaking multiple Netflix records. This blend of commercial success and respectful critical reception has amplified excitement for more movies starring Sandler. With his ongoing collaboration with Netflix, many fans are eager to explore his previous works while anticipating future releases.
Adam Sandler’s Halloween Adventure: Hubie Halloween (2020)
In Hubie Halloween, Sandler portrays a community volunteer who, despite being ridiculed by locals, finds himself tasked with solving a real murder on Halloween night. This film diverges tonally from the sports comedy style of Happy Gilmore 2, embracing elements of the horror genre mixed with comedy.
Interestingly, Hubie Halloween features Ben Stiller playing Hal L., the same unpleasant character he portrays in both Happy Gilmore films. Stiller’s memorable performance as Hal L. links the films distinctively, offering fans a familiar face in a fresh context. Additionally, Julie Bowen, who appears as Happy’s wife Virginia in Happy Gilmore 2, also stars in Hubie Halloween. Since her character dies early in Happy Gilmore 2, fans missing Bowen’s presence in the sequel can still enjoy her in this Halloween-themed comedy.
A Gripping Shift: The Crime Thriller Uncut Gems (2019)
Uncut Gems represents a departure from Sandler’s usual comedic style, presenting a tense crime thriller focused on a New York jeweler who wagers everything on a risky bet. The film is co-directed by Benny Safdie, who also plays the villain Frank Manatee in Happy Gilmore 2, highlighting a sustained creative partnership between Sandler and Safdie.
Safdie, primarily known as a director, has appeared in critically acclaimed movies like Oppenheimer and Licorice Pizza. His collaboration with Sandler in both Uncut Gems and Happy Gilmore 2 demonstrates a blending of intense dramatic storytelling and comedic performance. With an impressive 91% Rotten Tomatoes rating, Uncut Gems stands out as arguably one of Sandler’s finest works, particularly for viewers interested in his more serious acting roles.
Reliving Friendships in Grown Ups (2010)
Returning to classic comedy, Grown Ups centers on a group of childhood friends reuniting to honor their former basketball coach’s funeral, spending a weekend filled with humor and heartwarming moments at a cottage. This ensemble film features an all-star cast, including Kevin James, David Spade, Chris Rock, and Salma Hayek, adding to its widespread appeal.
The collaboration of such a popular cast helped Grown Ups become the highest-grossing live-action film in Sandler’s career. Fans of Happy Gilmore 2 will appreciate seeing another side of Sandler’s comedic skills, as well as the touching on-screen relationship with Cameron Boyce, who plays Sandler’s character’s son. Boyce tragically passed away in 2019, and a tribute to him was included in Happy Gilmore 2, making Grown Ups an especially meaningful watch.
Continuing the Laughter: Grown Ups 2 (2013)
Following the success of the first film, Grown Ups 2 reunites Sandler and the original cast for another fun-filled adventure. This time, Sandler’s character relocates his family from Los Angeles back to his hometown to reconnect with his lifelong friends, resulting in the same comedy-laden chaos fans enjoyed previously.
Like its predecessor, Grown Ups 2 performed well at the box office and also features Cameron Boyce reprising his role as Sandler’s son. This continuation offers more of the humor and heartfelt moments that resonate with fans of Happy Gilmore 2 and Sandler’s work in general.
Sports Comedy Highlight: The Longest Yard (2005)
Among Sandler’s sports-themed movies, The Longest Yard is a standout. In this 2005 remake of the 1974 film, Sandler plays Paul Crewe, a disgraced NFL quarterback imprisoned for point-shaving. In prison, Crewe organizes a football game between inmates and guards, combining action and comedy in an engaging sports tale.
The film boasts a strong supporting cast including Burt Reynolds—who led the original movie—alongside Chris Rock, Terry Crews, and well-known WWE wrestlers such as Bill Goldberg, Steve Austin, and Kevin Nash. For football fans, this movie offers an entertaining mix of sport and humor, showing how Sandler’s passion for sports has been a recurring influence throughout his acting career.
Classic Football Comedy: The Waterboy (1998)
The Waterboy features Sandler as Bobby Boucher, a shy water boy who turns into an unlikely hero for an underperforming college football team. After being fired, Bobby joins their rivals and leads them on an inspiring path to victory, blending charm, heart, and laughs in a traditional sports comedy format.
Released two years after the original Happy Gilmore, The Waterboy captures the early essence of Sandler’s comedic style that made him popular. Its feel-good storyline and iconic performances make it a vital addition for anyone looking to explore must-watch Adam Sandler movies after Happy Gilmore 2.
Heartwarming Humor in Big Daddy (1999)
Big Daddy introduces Sandler as Sonny, a man who adopts a five-year-old boy named Julian to prove his maturity to his ex-girlfriend. The movie explores their growing bond, mixing humor and heartfelt moments as Sonny struggles with his new parental role.
This film parallels Happy Gilmore 2 in its focus on family dynamics, as Happy is also shown trying to provide for his children, including efforts to support his daughter’s dance aspirations in Paris. Both films depict Sandler’s characters as flawed but ultimately loving fathers, making Big Daddy an emotionally resonant and entertaining choice for fans.
Early Success with Billy Madison (1995)
Billy Madison is the earliest film on this list, released before the original Happy Gilmore. Sandler stars as a spoiled wealthy child who must retake every grade from first through twelfth within 24 weeks to inherit his father’s fortune. His interactions with students across various ages fuel much of the film’s comedy.
This movie helped solidify Sandler’s reputation as a leading comedic actor and remains a fan favorite. Its blend of absurd humor and endearing moments make Billy Madison a foundational Adam Sandler must-watch movie, especially relevant after the excitement surrounding Happy Gilmore 2’s release.
These eight films illustrate the range and enduring appeal of Adam Sandler’s career, from heartfelt family stories to riotous comedies and gripping dramas. Whether viewers prefer classic laughter, sports antics, or serious performances, revisiting these titles after Happy Gilmore 2 offers a vibrant look at an actor who continues to shape comedy and film entertainment.
