With Hustle breaking Adam Sandler's Rotten Tomatoes score record, Sandler has never been more liked by movie critics than in this current phase of his career. Alongside his performance in Uncut Gems, it appears Sandler is finding a second wind with a more dramatic fare.
However, Sandler fans have seen peaks of his dramatic range in his other films as well, from heartfelt rom-coms like 50 First Dates to dramedies like Funny People. It only shows that comedians like Sandler also know how to challenge themselves with serious roles that further impress the audience and critics.
Happy Gilmore (1996)
Happy Gilmore follows an unsuccessful hockey player, who finds a newfound talent for golf. When his grandmother's house faces possible foreclosure, Gilmore embarks on an unlikely rise through the golf world to save her home.
As the titular character, Sandler blends the stakes of the movie with his signature slapstick humor, leading to memorable scenes like one opposite Bob Barker, Gilmore's pro-am partner. Critically panned when it was released, Happy Gilmore has held up as one of Sandler's more iconic comedic characters.
Billy Madison (1995)
Billy Madison tells the story of Sandler as the titular character, a childish heir to a Fortune 500 hotel company whose father bribed teachers so he would graduate high school. When his father loses confidence in Billy's ability to one day run the company, Billy offers to return to school to prove his competence.
One of the best movies written by Sandler, he dons his iconic voice to elevate scenes opposite children and define his comedic styling for decades to come. The film went on to be a commercial hit, proving Sandler's staying power beyond his Saturday Night Live fame.
50 First Dates (2004)
In his first Hawaii-based rom-com, 50 First Dates tracks a veterinarian Henry Roth, initially a playboy afraid of commitment, but falls in love with a woman that has short-term memory loss and his attempts to woo her over and over again.
The film's premise allows it to have more than its handful of visual jokes. However, the performance of Sandler as a man chasing love is ultimately what makes it compelling. Strengthened by his chemistry with Drew Barrymore, 50 First Dates is sprinkled with dramatic moments throughout.
Big Daddy (1999)
Against the backdrop of New York City, Big Daddy focuses on Sonny Koufax, a slacker with a law degree he doesn't use but finds his roommate's child dropped at his doorstep. While Sonny initially uses the kid to try and win his girlfriend back, the two develop a strong bond that leads Sonny to help take care of him.
While the rest of the film's set pieces add to the comedic story, it's the core heartfelt relationship between Sandler and the Sprouse twins that sold it to audiences. With less slapstick comedy compared to his other films, Sandler still manages to showcase his humorous flairs while also putting in a multi-layered performance.
Click (2006)
One of Sandler's first fantasy films, Click is about an architect who finds a remote that allows him to fast forward and reverse through different parts of his life. However, when the remote begins to override his choices, he must put family over his work and value his time with them.
Beginning with a comedic set-up, Click dives into deeper themes of commitment, family, and love as the film progresses. Even if these themes don't always connect, Sandler's ability to act comedically and dramatically simultaneously allows Click to shift tonally to a darker and more interesting place than with lesser performers.
The Wedding Singer (1998)
One of the best Adam Sandler-led rom-coms, The Wedding Singer looks at the relationship between Robbie, a singer, and Julia, a waitress, as they realize they should be with each other and not engaged to other people.
In their first collaboration together, Sandler and Barrymore pop off of the screen as mismatched lovers. Carrying his usual comedic charm, Sandler toned down his boyish instincts to give a convincing performance as a local rockstar turned wedding singer that drew filmmakers to cast him in more dramatic fare later in his career.
Funny People (2009)
Funny People is set in the stand-up comedy scene and follows George Simmons, a retired stand-up comedian who returns to the mic after being diagnosed with cancer. During his comeback, George reexamines his relationships and butts heads with his new assistant/aspiring comic Ira Wright.
Directed by Judd Apatow, Sandler finds the nuance in the laughs by creating a complicated character within a world in which he's familiar. Opposite a who's-who of his comedic contemporaries, Sandler's George stands out as a sad but lovable mess in Apatow's ode to comedians.
Punch-Drunk Love (2002)
Paul Thomas Anderson's most rewatchable film, Punch-Drunk Love revolves around Barry Egan, an anxious entrepreneur who falls in love with his sister's co-worker Lena. However, Barry's loneliness causes him to call a phone-sex line, leading to events that jeopardize his relationship with Lena.
Many critics saw Sandler's performance as a breakthrough from his usual fare up until that point, rating it higher than any of his previous films. This wasn't just due to Sandler's ability to subvert expectations, however, as the character of Barry withstands the test of time as one of his weightier, transformative roles.
Uncut Gems (2019)
Entrenched in the fast-paced world of the NYC Diamond District, Uncut Gems revolves around Howard Ratner, a fast-talking jeweler with a self-destructive gambling addiction. When Ratner believes he's got an opportunity to get out of financial ruin, he puts it all on the line for an uncut opal from Ethiopia.
Filled to the brim with unforgettable quotes, the high-tension thriller delivered Sandler some of the best reviews of his career. Sandler sets his comedy aside for a more neurotic, adrenalized, and often ironic performance, which surprised the audience and critics alike. While one of his most dramatic movies, Sandler proved his acting versatility in a more serious role, and if people did not notice this in his earlier works, they surely did in Uncut Gems.
Hustle (2022)
Based in the world of the NBA, Hustle depicts weary basketball scout Stanley Sugarman and his life searching for future star talent. While watching a pick-up game in Spain, Sugarman discovers an unknown player Bo Cruz and brings him back to the U.S. to prepare him for the NBA draft.
The clearest drama of Sandler's filmography, Hustle was praised for its authenticity and Sandler's researched, everyman performance. Unlike his other movies, Sandler takes a more personal and nuanced approach as the basketball scout. With the film focused on second chances and family, Sandler furthers his fantastic performance with an emotional weight that allows him to connect with Bo and build a father-son relationship on the court.