Adam Sandler has had one of the most unique Hollywood careers of any actor. He gained notoriety as a cast member on Saturday Night Live from 1990 to 1995 and piggybacked off that fame to launch his film career in the mid-90s. Starring in zany comedies like Airheads (1994), Billy Madison (1995), and Happy Gilmore (1996), Sandler found success playing over-the-top but lovable characters. These roles have largely defined his career and have resulted in films of wildly varying quality, from some genuinely hysterical comedies to some of the lowest-rated movies ever made.
Related: Best Adam Sandler Films
However, even the best of these films, though funny, don’t showcase much depth and emotional range from Sandler. That has led many critics to dismiss him as an unserious actor, but his latest role as Stanley Sugarman in the Netflix original Hustle affirmed his impressive acting chops, making this the perfect time to look back at, and rank, the occasions Sandler has stepped out of his comfort zone to deliver dramatic performances.
'The Cobbler' (2014)
In The Cobbler, Sandler stars as a down-on-his-luck shoemaker who finds a magical sewing machine that allows him to physically become his customers whenever he wears their shoes. That strange premise is only a taste of a bizarre plot that involves hitmen, real estate conspiracies, and Steve Buscemi feeding Sandler’s character pickles.
The result is a movie that was panned by critics. Sandler’s performance is what holds the story together. However, his character spends large portions of the movie in other people’s shoes/portrayed by other actors.
'Spanglish' (2004)
Spanglish stars Paz Vega as Flor, a Mexican immigrant and single mother who becomes the housekeeper for a wealthy American family. Sandler plays the father, a renowned chef who begins to bond with Flor, as his neurotic wife (Tea Leoni) becomes increasingly distant. Despite its romantic comedy premise, the film instead focuses on parenting and cultural divides, particularly Flor's struggle to raise her daughter and instill cultural values, as Sandler’s wife, seemingly in the midst of a midlife crisis, continues to overstep boundaries while “parenting” Flor’s daughter.
Sandler’s performance was one of the few bright spots. His chemistry with Paz Verga is strong, and he was convincing as a caring father and jaded husband.
Related: Best Adam Sandler Comedies
'Funny People' (2009)
Perhaps Sandler’s most depressing film, Funny People is about George Simmons, a retired stand-up comedian who returns to the mic after being diagnosed with a rare and fatal blood disease. While struggling with the thought of his imminent death, he decides to befriend a struggling comic named Ira (Seth Rogen) and reconnect with an old flame (Leslie Mann). However, when the disease goes into remission, George gets a chance to re-evaluate his life and figure out what is truly important to him.
Writer-director Judd Apatow wrote the part specifically for Sandler, his former roommate, crafting a fictional, depressed version of him – a rich and famous comedian who has everything he could ever want except family, friends, and good health. Sandler clearly related deeply to the material, resulting in one of his strongest emotional performances. He was truly believable as a man dealing with an existential crisis, and his eyes brim with grief and regret.
'The Meyerowitz Stories' (2017)
After a long hiatus from serious roles, Sandler teamed up with writer-director Noah Baumbach (Marriage Story) in 2017 for The Meyerowitz Stories,portraying Danny, the eldest son of a narcissistic, undiscovered sculptor (Dustin Hoffman) who has recently retired from his life as an art professor. After Danny sends his daughter off to college, he comes back home to spend time with his dad and organizes a retrospective art show for his father's work with his sister Jean (Elizabeth Marvel). As the art show approaches, a family crisis brings them all together, including the youngest and favored son, Matt (Ben Stiller).
Sandler turns in one of the best performances of his career as a failed musician who resents his highly successful brother and feels unfulfilled due to the constant disproval of his father. In a stacked cast with plenty of standout performances, much of the film’s praise still centered around Sandler, highlighting just how good he was in the film.
'Hustle' (2022)
It’s well documented that Sandler is a passionate basketball fan who spends his free time playing pickup games with strangers at the park. That passion shines in his most recent film, Hustle, the story of a down-on-his-luck basketball scout Stanley Sugarman who discovers a talented but unknown player dominating pick-up basketball in Spain. After feeling disrespected by his team’s manager, Sugarman quits his job, becoming the player’s trainer and agent and betting it all on preparing him for the NBA Draft.
Hustle was deservedly praised for its emotional resonance and Sandler's nuanced performance as a weary, unfulfilled scout. The film focused on second chances and family, wherein Sandler elevates his fantastic performance with his powerful fatherly relationship with Bo (portrayed surprisingly well by actual NBA player Juancho Hernangomez). This is definitely one of Sandler’s best performances and is a feel-good movie well worth checking out on Netflix.
Related: Movies To Stream If You Loved Adam Sandler's 'Hustle'
'Reign Over Me' (2007)
Reign over Me stars Don Cheadle as Alan Johnson, a successful dentist who tries to help his former college roommate Charlie Fineman, a man who has isolated himself from society after losing his family in the terrorist attacks of Sept. 11. Sandler initially passed on the role, but eventually agreed, and it was not the wrong choice.
Sandler really shines in the role, with a heartbreaking portrayal of a tormented man attempting to avoid dealing with his trauma. He’s particularly devastating in the scene above where he finally opens up to Alan.
'Punch-Drunk Love' (2002)
Legendary director Paul Thomas Anderson turned his attention to Sandler with his 2002 dark-comedy/romance Punch-Drunk Love. As a huge fan of Sandler’s comedies, Anderson crafted a film that played on the typical tropes but subverted them in dramatic ways. The plot centers around anxious and lonely entrepreneur Barry Egan (Sandler) falling in love with his sister's co-worker, Lena Leonard (Emily Watson), while a con artist attempts to extort him.
Sandler’s role as Barry plays off what he does best but pokes deeper at the insecurities and external forces that forge such a character. His self-deprecating humor becomes full-on clinical depression. Sandler thrives as an anxious introvert with serious anger issues. Sandler's performance earned him a Golden Globe nomination and much-deserved critical acclaim. This was the first time Sandler proved he could thrive in a serious role, and it remains one of his best performances.
'Uncut Gems' (2019)
.jpg)
Easily taking the top spot is the Safdie Brothers’ 2019 drama-thriller Uncut Gems. In it, Sandler puts on an all-time memorable performance as Howard Ratner, a fast-talking jewelry dealer with a self-destructive gambling addiction. Filled to the brim with tension, this anxiety-inducing thriller is carried by Sandler’s mesmerizing performance, with the whole story revolving around his character and seldom a shot without him in the frame.
Audiences could truly feel the obsession in his eyes, as a man that craves constant gratification and is addicted to the thrill of risk. The audience loses Sandler in this role, to the point where we just see Howard. Sandler should have been nominated for an Oscar but was unfortunately snubbed. He did, however, pick up an Independent Spirit Award for his performance.
