8 Times Adam Sandler Went Serious For A Movie And It Paid Off

Adam Sandler is a household name mainly known for his comedic range throughout the ’90s that included hits such as Billy Madison (1995), Happy Gilmore (1996), The Wedding Singer (1998), The Waterboy (1998), and Big Daddy (1999) — just to name a few. However, as his career continued to expand into the 21st century, so did his range of film genre he began starring in. Proving to be more than just the funny Sandman, he began showing audiences breakout dramatic performances in serious roles. Here is the brief but thorough breakdown of that dramatic deviation.

2002: Punch-Drunk Love

Photo: Sony Pictures Releasing

In 2002, Sandler made his first foray into dramatic work with Punch-Drunk Love. After starring in five smash movies in a row, Sandler hit his first commercial disappointment with 2000’s Little Nicky. While he was pragmatic enough to know to make another classic Sandler mainstream comedy with 2002’s Mr. Deeds, he also took the opportunity for a career transition with a more creatively ambitious choice.  

In Punch-Drunk Love, Sandler plays a business owner with social anxiety and a lonely life – a clear departure from his usual cool guy characters. In prior films, Sandler used anger as a comedic tool, but in this dramatic role, his sporadic rage is the result of repeated emotionally abuse at the hands of his family.  

The Paul Thomas Anderson-helmed drama didn’t turn a profit, but it received positive reviews, opening the door for Sandler to continue to explore dramatic roles. Roger Ebert noted that Sandler was “liberated from the constraints of formula” and revealed “unexpected depths as an actor.”

2004: Spanglish

Photo: Columbia PIctures

Director James L. Brooks cast Sandler in Spanglish after seeing him in Punch-Drunk Love. Sandler plays John, a chef in a popular Los Angeles eatery who strikes up a friendship with his housekeeper Flor (Paz Vega). The easy-going family man is a stark contrast to his wife Deborah (Tea Leoni), an insecure woman who masks her uncertainties by being controlling. His character also experiences darker and more complicated subject matters than audiences were used to seeing from Sandler, such as infidelity and anxiety. 

Spanglish fell short at the box office and received mixed reviews from critics, although Sandler did win critical approval for his thoughtful and moving performance.

2007: Reign Over Me

Photo: Columbia PIctures

In Reign Over Me, Sandler tackles dark subject matter in the role of Charlie Fineman, a man whose life is ruined after the loss of his wife and daughters in the 9/11 attacks. The role was easily Sandler’s heaviest dramatic role yet, as his character struggles with the concepts of loss, self-harm, and mental illness.

While critics took issue with portions of the film, Sandler’s performance was praised. Andrew Pulver of The Guardian noted that “without Sandler, Reign Over Me would be a gloopy, post-9/11 love-in, making cavalier use of a fine but helpless cast.”

2009: Funny People

Photo: Universal Pictures

For Funny People, Sandler teamed up with his former roommate, director Judd Apatow, for a dark comedy. Sandler plays George, a massively successful comedian turned movie star turned real jerk who is diagnosed with a terminal illness. Parallels to his own career made Sandler an interesting choice for the role, but this was the first time he played an unlikeable person, as all of his previous characters had their “good guy” moments. 

Despite his abrasive and destructive nature as George, Sandler’s innate likability makes the audience root for the character. Peter Travers from Rolling Stone described Sandler as “relaxed, focused, alert to nuance,” and called it “his best performance ever.”

2014: Men, Women & Children

Photo: Men, Women & Children

Directed by Jason Reitman and based on the novel of the same name, Men, Women & Children tackles the very modern problem of internet dependency. Sandler plays opposite Rosemarie DeWitt as a married couple stuck in a rut who are driven further apart by the romantic opportunities offered online.

Despite its big name cast, the film’s wide opening was abysmal and the film received mostly negative reviews. Still, Rafer Guzman of Newsday noted that “fine performances from Sandler and DeWitt help give the storyline an emotional underpinning.”

2015: The Cobbler

Photo: Image Entertainment

In Tom McCarthy’s The Cobbler, Sandler takes a swing at magical realism by playing a Jewish cobbler in New York with a mystical stitching machine that allows him to transform into different people and live a day in their shoes. The critics were especially harsh on both Sandler’s performance and the movie, with one noting, “Sandler had an opportunity to explore ethnicity, family and mortality. He botches the whole thing.”

While it only received a very limited release, it became Sandler’s biggest commercial flop ever, earning only $24,000 in its opening weekend.

2017: The Meyerowitz Stories

Photo: Netflix

Directed by Noah Baumbach, The Meyerowitz Stories stars Sandler, Ben Stiller, and Dustin Hoffman and became the darling of Cannes. In the film, Sandler plays a man whose marriage and professional life have fallen apart, so he must move back in with his father and his father’s third wife.

The film holds an excellent 93% fresh rating on Rotten Tomatoes, and much of the acclaim was directed at Sandler’s performance. A review of the film in The Atlantic was actually titled, “Adam Sandler Does His Best Work Yet.”

2019: Uncut Gems

Photo: A24

For his performance as Howard Ratner in Uncut Gems, Sandler received some of the best reviews of his career. Directed by Josh and Benny Safdie, the fast-paced drama finds Sandler as a jeweler whose gambling problem amounts to serious debt.

Michael O’Sullivan from The Washington Post noted that “Sandler is so good, so committed and so watchable that… you can’t take your eyes off the screen.” Joceyln Noveck from the Associated Press remarked on Sandler’s ability to connect emotionally, adding, “He deserves the accolades he’s getting, again proving that with the right material, he has an uncanny ability to reach deep within us.” And Deadline called him “a revelation” in the role.