Instead of being a career-ending event for most comedians, getting fired from “Saturday Night Live” proved to be a turning point for Adam Sandler as it paved the way for him to establish himself as one of Hollywood’s top leading men. Following movies like “Billy Madison,” “Happy Gilmore,” “The Waterboy,” and “The Wedding Singer,” Sandler shared his unique brand of offbeat humor with audiences worldwide. These films, while enjoyed by many, were not universally praised by critics, and Sandler gained a reputation as an outcast among snobbish movie connoisseurs.
The dynamic shifted significantly with “Punch-Drunk Love,” a film directed by the revered figure in cinematography circles, Paul Thomas Anderson. Instead of completely veering away from his origins following his major critical success, Sandler has been oscillating between nuanced roles in art house films and traditional Happy Madison comedies. As his standing among serious film enthusiasts has improved, there’s been a reevaluation of his earlier works, revealing that the foundations of his dramatic performances were laid even in his most comedic roles. Few can claim both six Razzie Awards and an Independent Spirit Award, but such is the unconventional career trajectory of Adam Sandler. Here are 15 of his best movies, ranked.
15. The Waterboy
The film “The Waterboy” was influenced by one of Adam Sandler’s characters from “Saturday Night Live,” Canteen Boy, who was a water-loving boy scout in a well-known sketch with Alec Baldwin’s character, a predatory scoutmaster. In essence, the character can be likened to ‘Canteen Boy,’ as he shares a fondness for water and they both face a lot of teasing. However, what Sandler appreciates most about this character is his authenticity and kindness. This endearing individual resonated with viewers, and the offbeat comedy earned $190 million globally upon release.
In this role, Sandler portrays Bobby Boucher, a 31-year-old assistant for the University of Louisiana’s football squad. His emotional development has been hindered by his domineering mother, Mama (Kathy Bates), who despises football, referring to it as “The Devil.” Despite Coach Klein’s (Henry Winkler) wishes for Bobby to join the team, his mother refuses, fearing the impact of football. However, with assistance from his new girlfriend Vicky (Fairuza Balk), Bobby realizes and embraces his hidden ability in tackling when enraged, ultimately fulfilling his destiny.
Cast: Adam Sandler, Kathy Bates, Fairuza Balk, Jerry Reed, Henry Winkler
Director: Frank Coraci
Rating: PG-13
Runtime: 90 minutes
Where to watch: Hulu
14. Anger Management
Anger Management” was produced a year after “Punch-Drunk Love,” indicating that Adam Sandler wasn’t completely abandoning his comedic background for more serious, artistic endeavors. In essence, it’s a contrast to his more dramatic role, delving deeper into the simmering anger hidden behind his friendly demeanor. Notably, this film is a Happy Madison production, filled with humor through numerous goofy jokes and guest appearances by celebrities, including Rudy Giuliani, former mayor of New York City.
Following a heated altercation on an airplane escalating into a major tantrum, easygoing Dave Buznik is mandated to attend anger management sessions with Dr. Buddy Rydell (played by Jack Nicholson). Dr. Rydell employs some non-standard treatment methods, and soon enough, he becomes deeply involved in Dave’s life, particularly his romantic relationship with Linda (Marisa Tomei). The combination of Sandler and Nicholson proves to be a hilarious duo as they continuously outdo each other with their outrageous behavior.
Cast: Adam Sandler, Jack Nicholson, Marisa Tomei, Luis Guzmán, Woody Harrelson, John Turturro
Director: Peter Segal
Rating: PG-13
Runtime: 106 minutes
Where to watch: Hulu
13. Murder Mystery
Initially criticized for his Netflix contract following the poor reception of “The Ridiculous 6” with a zero percent rating on Rotten Tomatoes, Adam Sandler has also produced some of his finest works under this deal. One such film is “Murder Mystery,” which led to a sequel in 2023. In this movie, Sandler portrays Nick Spitz, a New York City police officer who embarks on a long-awaited European vacation with his wife Audrey (Jennifer Aniston). During their flight across the continent, they encounter an engaging billionaire (Luke Evans), who invites them to his uncle’s (Terence Stamp) wedding on a yacht. However, upon arriving at the celebration, the groom is found murdered, and the Spitzes are unexpectedly thrust into the role of amateur sleuths.
The movie ‘Murder Mystery’ can be seen as a comedic adaptation similar to Happy Madison productions of the classic ‘Thin Man’ series, featuring William Powell and Myrna Loy as sophisticated detective duo Nick and Nora Charles. It’s also one of the most entertaining movies in the Adam Sandler vacation film genre, where the storyline serves as an excuse for a getaway with his humorist companions. Much like a memorable vacation, ‘Murder Mystery’ is full of enjoyable moments.
Cast: Adam Sandler, Jennifer Aniston, Luke Evans, Terence Stamp, Gemma Arterton
Director: Kyle Newacheck
Rating: PG-13
Runtime: 97 minutes
Where to watch: Netflix
12. Hubie Halloween
Adam Sandler produced a timeless Halloween favorite with “Hubie Halloween,” which premiered on Netflix. The film focuses once again on a Sandler character, Hubie Dubois, who endures constant mockery from the people of Salem, Massachusetts. On Halloween night, Hubie steps up to become the town’s Halloween Assistant. However, this year, an actual murder mystery compels Hubie to rise to the occasion and prove himself as the hero Salem requires.
In his critique for USA Today, Brian Truitt compared “Hubie Halloween” to a small, delectable Baby Ruth candy bar found in a bag of treats – it’s sweet, sticky, nutty, and fulfilling. Essentially, this is a strong recommendation for the movie, as it doesn’t aim to revolutionize anything but instead offers just what fans of Adam Sandler have come to anticipate from Happy Madison Productions: A plethora of silliness and a generous dose of heart. It’s an ideal choice for those who prefer spending Halloween at home rather than going trick-or-treating.
Cast: Adam Sandler, Kevin James, Julie Bowen, Ray Liotta, Rob Schneider, June Squibb, Steve Buscemi
Director: Steven Brill
Rating: PG-13
Runtime: 103 minutes
Where to watch: Netflix
11. Click
In “Click,” Adam Sandler takes on the role of Michael Newman, an architect yearning for a work-life balance, specifically more time at home with his spouse (Kate Beckinsale) and children. He encounters an inventor (Christopher Walken), who bestows upon him a magical TV remote capable of manipulating the universe. Eager to leap over life’s tedious phases to reach the enjoyable parts sooner, Michael eventually discovers that he must cherish each moment bestowed upon him, including those he wishes to avoid.
Beneath each Adam Sandler comedy lies a tender spirit, often concluding with a moral emphasizing the value of family and companionship. This is true for the movie “Click,” which can be seen as a modern-day reinterpretation of “It’s a Wonderful Life” with a touch of the quirky humor typical of Happy Madison Productions. Notably, “Click” holds a unique position in Sandler’s filmography because it was his first (and currently only) production to receive an Oscar nomination – for best makeup, although it ultimately lost to “Pan’s Labyrinth.
As a gaming enthusiast, I’d put it this way: “Star-studded cast includes Adam Sandler, Kate Beckinsale, Christopher Walken, the legendary Henry Winkler, the Hoff himself – David Hasselhoff, Julie Kavner, and the versatile Sean Astin.
Director: Frank Coraci
Rating: PG-13
Runtime: 107 minutes
Where to watch: Tubi
10. Hustle
Adam Sandler’s fondness for basketball is evident, as he’s frequently spotted at public functions in attire more appropriate for a court than a formal event. This enthusiasm found a productive outlet in “Hustle,” where he garnered his initial SAG nomination for best actor. In the movie, he portrays Stanley Sugarman, a disheartened talent scout harboring aspirations of becoming a coach. During his time in Spain, he encounters Bo Cruz (real-life NBA player Juancho Hernangómez), who excels at street basketball. Convinced that Bo has the potential to go pro, Stanley brings him back to the U.S., setting off a journey towards redemption.
In a somewhat surprising turn, one of Adam Sandler’s Netflix projects, titled “Hustle”, has received some of his most positive reviews yet. This may not seem like much given that it competes with films such as “The Do-Over” and “Sandy Wexler”. However, David Ehrlich from Indiewire was quite enthusiastic, remarking that if Sandler continues to work diligently, the man who was once synonymous with Netflix’s embrace of mediocrity could potentially become their most valuable asset.
Starring: Adam Sandler, Queen Latifah, Juancho Hernangómez, Ben Foster, Robert Duvall
Director: Jeremiah Zagar
Rating: R
Runtime: 118 minutes
Where to watch: Netflix
9. Big Daddy
Most Adam Sandler films feature a character who is immature and must reluctantly grow up, which is poignantly demonstrated in the film “Big Daddy.” This was one of Sandler’s early attempts to blend emotion with humor. In this movie, he portrays Sonny Koufax, a 32-year-old man who urgently wants to prove his maturity after his girlfriend (Kristy Swanson) leaves him. To show he can be responsible, he agrees to look after the long-lost son of his roommate (Jon Stewart), Julian (Cole Sprouse and Dylan Sprouse). Despite his ex’s disapproval, Sonny continues caring for Julian when he finds out that the boy will be placed in foster care.
Despite Sandler receiving a Razzie for worst actor, his portrayal in “Big Daddy” showcases a path towards his later, more grounded dramatic roles. Notably, Paul Thomas Anderson is an acknowledged admirer of the film, and this likely influenced his decision to cast Sandler in “Punch-Drunk Love.
Characters: Adam Sandler, Joey Lauren Adams, Jon Stewart, Rob Schneider, Cole Sprouse and Dylan Sprouse, along with Leslie Mann
Or
Actors/Actresses: Adam Sandler, Joey Lauren Adams, Jon Stewart, Rob Schneider, Cole Sprouse and Dylan Sprouse; also featuring Leslie Mann.
Director: Dennis Dugan
Rating: PG-13
Runtime: 93 minutes
Where to watch: Netflix
8. 50 First Dates
In terms of significant creative partners, Drew Barrymore ranks high for Adam Sandler, following the likes of Rob Schneider, having collaborated on just three films together. Ranging from the success of “The Wedding Singer” to the less successful “Blended,” their joint productions include “50 First Dates,” a film where Sandler portrays Henry Roth, a Hawaiian marine veterinarian who develops feelings for art teacher Lucy Whitmore (Barrymore). However, their relationship is complicated by Lucy’s short-term memory loss, causing her to forget the events of each day upon waking.
Despite its seemingly insoluble premise, “50 First Dates” manages to thrive, largely due to the captivating chemistry between Sandler and Barrymore. As with most of Sandman’s films, there’s a warm, sugary core at the heart of this movie, making it delightful to witness Henry’s tireless efforts to win Lucy’s affection time and again.
Cast: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin, Dan Aykroyd
Director: Peter Segal
Rating: PG-13
Runtime: 99 minutes
Where to watch: Netflix
7. Funny People
Over the past few years, Adam Sandler has filmed several standup specials, which might be seen as compensating for the fact that he hadn’t done any before getting a job on “Saturday Night Live.” This background makes his portrayal in Judd Apatow’s film “Funny People,” a complex and moving dramedy, even more poignant. In many aspects, “Funny People” functions as a commentary on Sandler’s entire career, delving into his life as a comedian, an actor, and as an individual.
In a new take, Sandler portrays George Simmons, a renowned comedian who receives a devastating cancer diagnosis. Facing his impending mortality, he re-enters the standup scene and enlists an up-and-coming comic (Seth Rogen) as his joke writer. As fate would have it, he discovers that his illness is in remission, prompting him to reconcile with a former love (Leslie Mann), who’s now married with children. Much like the poignant humor found in the works of James L. Brooks, whom Sandler collaborated with on “Spanglish,” “Funny People” skillfully blends laughter and sorrow, making comedy out of pain and finding pathos within humor.
Cast: Adam Sandler, Seth Rogen, Leslie Mann, Eric Bana, Jonah Hill, Jason Schwartzman
Director: Judd Apatow
Rating: R
Runtime: 146 minutes
Where to watch: Max
6. Billy Madison
As a gamer, I remember my early roles in films like “Airheads” and “Mixed Nuts,” but it was “Billy Madison” that truly cemented me as the leading man. In this movie, I play Billy Madison, a character who’s as dimwitted as he is a hotel heir. My father, portrayed by Darren McGavin, has had enough of my lazy ways and decides to put his foot down. You see, I’ve never actually attended school because I could always skip it with my dad’s money. But now, my father challenges me to redo my entire education, from first grade all the way through 12th, in just 24 weeks. If I can’t manage it, I stand to lose control of our family empire to Eric Gordon, a cunning vice president played by Bradley Whitford. It’s like a real-life video game level I have to conquer!
Under the pen of Sandler and Tim Herlihy, “Billy Madison” marked the debut of Sandman’s distinct filmmaking style. The hallmarks that would become synonymous with his work – the immature protagonist, absurd humor, and eccentric sidekicks – are all evident in this movie. With “Billy Madison,” Sandler launched his career by scoring a box office success.
Cast: Adam Sandler, Bradley Whitford, Josh Mostel, Bridgette Wilson, Norm Macdonald, Darren McGavin
Director: Tamra Davis
Rating: PG-13
Runtime: 89 minutes
Where to watch: Peacock
5. Happy Gilmore
On an individual joke-by-joke analysis, “Happy Gilmore” could be Adam Sandler’s funniest comedy. This film is particularly revealing as it exposes the anger that lies beneath many of his characters. Despite his name suggesting happiness, golf player Happy Gilmore (Sandler) is actually quite angry, especially about his inability to skate. When his grandmother (Frances Bay) is threatened with eviction, he takes up professional golfing to earn enough money to cover her mortgage. With the aid of his one-armed coach, Chubbs (Carl Weathers), and his girlfriend, Virginia (Julie Bowen), Happy transforms his anger into a golf swing potent enough to outdo Shooter McGavin (Christopher McDonald).
In the movie “Happy Gilmore,” Adam Sandler delivers some of his funniest moments, with a memorable brawl between him and Bob Barker, known for hosting “The Price is Right.” However, beneath the humor lies a deeper exploration of his on-screen character – a grown man with developmental issues who is both charmingly naive and explosively volatile. This duality is evident in Sandler’s finest performances, and Happy Gilmore is undoubtedly one of them.
Cast: Adam Sandler, Christopher McDonald, Julie Bowen, Carl Weathers
Director: Dennis Dugan
Rating: PG-13
Runtime: 92 minutes
Where to watch: Amazon Prime
4. The Meyerowitz Stories (New and Selected)
In the cinematic marvel that boasts an array of Academy Award winners, it’s Adam Sandler who truly shines in Noah Baumbach’s “The Meyerowitz Stories (New and Selected)”. I step into the shoes of Danny Meyerowitz, a man who finds himself back under the same roof as my father, Harold – a renowned sculptor and retired professor, played by Dustin Hoffman. My father shares this home with Maureen, his free-spirited wife portrayed by Emma Thompson.
After a tumultuous divorce, I return to find my successful financier brother Matthew (Ben Stiller) and our sister Jean (Elizabeth Marvel) also back home. The occasion is a retrospective of our father’s work. But when Harold takes a fall, we, his children, are suddenly confronted with the harsh reality of possibly losing him forever.
In typical Baumbach fashion, “The Meyerowitz Stories” exhibits intelligence, wit, and a certain spikiness. Adam Sandler portrays the film’s emotional core as a man scarred by his domineering father, striving to shield his daughter Eliza (Grace Van Patten) from similar harm. This is another instance of Sandler demonstrating his acting range, moving beyond the slapstick humor that brought him initial fame.
Cast: Adam Sandler, Ben Stiller, Dustin Hoffman, Emma Thompson, Elizabeth Marvel
Director: Noah Baumbach
Rating: TV-MA
Runtime: 112 minutes
Where to watch: Netflix
3. The Wedding Singer
Among Adam Sandler’s early movies, “The Wedding Singer” is arguably his best at combining zany humor with genuine emotional sincerity. It has also been remarkably re-evaluated as a timeless piece, leading to a Tony-nominated Broadway musical adaptation. Given its narrative structure and charm, it’s not surprising that it translates so well to the stage, as it shares characteristics with classic dance films like those of Fred Astaire and Ginger Rogers, but with a distinctly Happy Madison twist.
1985 serves as the backdrop for my account of a heartwarming tale, where I find myself in the shoes of Robbie Hart, a wedding singer from New Jersey. My own dreams of marital bliss are shattered when my fiancee Linda calls off our wedding, leaving me heartbroken. However, fate leads me to Julia Sullivan, a sweet-natured waitress who’s already promised to another man – Glenn Gulia. Despite agreeing to sing at their nuptials, I harbor a secret hope of winning Julia’s affection instead. From the moment my character shares the screen with Julia (played by Drew Barrymore), it’s clear where “The Wedding Singer” is headed, yet we can’t help but cheer them on as they navigate their way towards love.
Cast: Adam Sandler, Drew Barrymore, Christine Taylor
Director: Frank Coraci
Rating: PG-13
Runtime: 97 minutes
Where to watch: Peacock
2. Punch-Drunk Love
As a devoted fan, I must say that when Adam Sandler ventured into the realm of “Punch-Drunk Love,” it was like witnessing a remarkable shift in gears. But what truly makes Paul Thomas Anderson’s artistic masterpiece stand out is its essence – it’s an Adam Sandler film, just one with deeper layers and keen insights. In this movie, Sandler portrays Barry Egan, a man who’s deeply melancholic and occasionally erupts in unexpected bursts of aggression. He finds himself smitten by the ethereal Lena Leonard (Emily Watson), and strives to amass enough frequent-flyer miles from a Healthy Choice food promotion to reunite with her in paradise. However, their budding romance is put to the test by the cunning phone sex scammers masterminded by mattress magnate Dean Trumbell (Philip Seymour Hoffman).
In his review, Roger Ebert noted that when directed by someone who sees beyond the typical Sandler persona as a mask for a complex outsider character, Sandler showcases layers and nuances we might have sensed but never clearly perceived, resulting in a performance that earned him his first Golden Globe nomination.
Cast: Adam Sandler, Emily Watson, Philip Seymour Hoffman, Luis Guzmán
Director: Paul Thomas Anderson
Rating: R
Runtime: 95 minutes
Where to watch: Amazon Prime
1. Uncut Gems
It’s surprising to think that 20 years after receiving a Razzie for “Big Daddy,” Adam Sandler would go on to win an Independent Spirit Award for “Uncut Gems.” However, considering the diversity of his film career spanning both commercial flops and critically-acclaimed indie films, this progression seems fitting. In this movie, Sandler portrays Howard Ratner, a jeweler in New York’s Diamond District who has accumulated significant debt from betting on basketball games. He believes the solution to his financial woes lies in a rare black opal, which he hopes will provide enough funds to pay off his ruthless loan shark brother-in-law (Eric Bogosian). As Howard’s troubles escalate, he only manages to dig himself further into the self-created pit of debt.
As a gaming enthusiast, I’d put it like this: “Playing ‘Uncut Gems’ feels like the peak of Adam Sandler’s abilities, showcasing both his frustrating and fascinating sides that have kept us hooked for over three decades.” This reflects Oliver Jones’ perspective from The Observer, where he describes Sandler’s career as a love-hate relationship with critics.
Cast: Adam Sandler, LaKeith Stanfield, Julia Fox, Kevin Garnett, Idina Menzel, Eric Bogosian
Directors: Josh Safdie, Benny Safdie
Rating: R
Runtime: 135 minutes
Where to watch: Amazon Prime
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2025-05-19 14:34