Adam Sandler has been a significant figure in Hollywood ever since his breakthrough on Saturday Night Live in the early 1990s. He became a box office powerhouse as one of cinema's most dependable comedy stars. Sandler's films though often missed critical praise became frequently quoted favorites among fans.
In the 21st century Sandler's career experienced both peaks and valleys. Some of his comedies were even called the worst of their respective decades. However he also broadened his acting range taking on diverse roles and collaborating with respected directors. With a profitable deal at Netflix and numerous projects underway the Sandman shows no sign of slowing down. Therefore it is a good moment to revisit the most vital movies of his career.
Ranking 10 Must-See Adam Sandler Films Reflecting His Career
From Waterboy's Goofy Charm to Uncut Gems' Intensity
Here are 10 essential Adam Sandler movies that showcase his comedic talent dramatic range and enduring appeal:
1. Uncut Gems (2019): Sandler's High-Stakes Thriller
It is always interesting when comedic actors explore darker roles. Audiences appreciated it when Robin Williams did it in One Hour Photo or Steve Carell in Foxcatcher. They were completely taken by Sandler in the Safdie Brothers' gambling thriller Uncut Gems. The movie unsettles viewers from the start and maintains that tension for over two hours. Sandler plays Howard a jeweler in New York's Diamond District with a serious gambling problem. He displays a wound-up anxiety unseen in his earlier performances.
The Safdies heighten the tension similar to their heist thriller Good Time and Sandler is perfect throughout. He constantly keeps viewers on edge hoping his character will make sound choices before his addiction overwhelms him. It is a fully committed performance that was unfortunately overlooked by major awards but it proves Sandler remains a consistently underestimated actor.
2. Punch-Drunk Love (2002): An Arthouse Rom-Com Surprise
The collaboration between Sandler and director Paul Thomas Anderson known for Boogie Nights and Magnolia was unexpected. Even now the film feels somewhat out of place in the director's filmography. However they proved to be an ideal pairing for Punch-Drunk Love a melancholic romantic comedy that goes beyond typical genre clichés. Sandler portrays Barry a socially isolated man prone to sudden anger. He encounters Emily Watson's Lena and their romance unfolds filled with odd moments including a memorable appearance by Philip Seymour Hoffman.
While this arthouse romantic comedy was not a box office success its reputation has grown among filmmakers. It also convincingly showed Sandler's potential for greater acting depth than previously recognized. Sandler mentioned in retrospect that this film directly influenced his career expansion beyond broad comedies.
3. The Wedding Singer (1998): Sandler's Romantic Comedy Peak
Back when romantic comedies frequently graced theaters Sandler was a top earner in the genre. Drew Barrymore was his most successful co-star. Even if their films were not always critically acclaimed the two actors consistently enhanced each other's performances. The Wedding Singer stands as their finest collaboration and a career highlight for Sandler.
Sandler plays Robbie Hart a wedding singer heartbroken after being jilted at the altar. He then finds new love with Barrymore's character Julia a waitress who is also engaged. The movie retains much of the silly humor characteristic of Sandler's work at that time. Yet it also allowed him to demonstrate more dramatic ability than he had previously been given. The Wedding Singer showcased Sandler's subtle range years before art-house directors recognized it and it did so while still including a rapping grandmother.
4. The Meyerowitz Stories (New and Selected) (2017): Underrated Dramatic Performance
Sandler's most underappreciated performance is in this dramedy about a troubled New York family. The Meyerowitz Stories centers on a family led by Dustin Hoffman as a retired art professor. Sandler plays Danny the older brother at a life turning point after divorce. Ben Stiller is his more successful brother Matthew. Sandler and Stiller compete for their father's approval and the two comedic actors share wonderfully tense chemistry alongside Hoffman who hides his character's insecurities behind criticism.
Sandler has repeatedly demonstrated his ability to excel beyond the exaggerated characters that made him famous. Reign Over Me though uneven film addressing post-9/11 grief is elevated by Sandler’s acting. Spaceman's bizarre concept is grounded by Sandler's naturalistic approach. Noah Baumbach the director effectively uses Sandler's strengths such as comedic frustration and musical talent to serve a relatable character. They apparently enjoyed working together as they are collaborating again on another Netflix project with George Clooney.
5. Happy Gilmore (1996): Pure Sandler Comedy Gold
Forget about surprising dramatic performances. What audiences truly enjoy is Adam Sandler being funny. He has never been funnier than in Happy Gilmore. As an aggressive hockey player who turns to golf to save his grandmother's house Sandler’s distinct comedic timing and style have never been better used. Also his scene getting punched by Bob Barker is comedic brilliance. No further explanation needed.
The movie's humor is amplified by excellent supporting performances. Carl Weathers plays on his sports movie persona as Sandler's golf mentor. Comedy pros Ben Stiller and Joe Flaherty both have hilarious smaller parts. However the MVP award goes to Christopher McDonald as Shooter McGavin. He is one of the best comedic villains ever with a questionable breakfast choice. It is unlikely that the planned Netflix sequel can recapture the comedic magic of this original. Yet Sandler's achievement with this comedy classic remains secure.
6. Hustle (2022): Sandler's Winning Sports Story
Sports have been a significant theme in Sandler's movie career. Hustle his latest sports film stands out because it is not a wacky comedy. It is genuinely well-made. Sandler plays an NBA talent scout whose career has taken a personal toll. When he discovers a raw talent in a Spanish basketball player (played by real-life sports star Juancho Hernangómez) he finds renewed purpose in his life and career.
It is the kind of underdog sports story that easily appeals to audiences. Sandler’s subtle performance and natural charm elevate it beyond sports movie clichés. Hustle is among the best Sandler films from his long-term Netflix deal and ranks high among his more serious performances.
7. Funny People (2009): Self-Reflection and Industry Humor
Sandler has rarely cared about critics' opinions of his work. He enjoys making movies with his friends and having fun. There is nothing inherently wrong with that. Only once has Sandler shown genuine self-reflection in his career in Judd Apatow's Funny People. Sandler plays a fictionalized version of himself (without wife and kids) a once-loved comedian now known for bad high-concept films who receives a life-changing medical diagnosis.
Apatow pairs Sandler with Seth Rogen as an aspiring comedian who Sandler takes under his wing. Not everything in the movie works perfectly. Apatow's directing had become somewhat self-indulgent by this point and the film is too long. However there is still sharp humor about Sandler's career and the entertainment industry in general. The biggest irony is how quickly Sandler returned to the juvenile comedies this film largely mocked proving he always gets the last laugh.
8. Billy Madison (1995): Sandler's Absurdist School Days
Sandler's first major lead role Billy Madison is his childish comedic persona at its most surreal. The movie's premise is so ridiculously brilliant. Sandler plays Billy Madison a spoiled rich kid who must repeat all his primary and secondary education classes to inherit his family's fortune.
The absurd plot simply serves as a stage for Sandler's antics in various school settings and that is enough to sustain the entire movie. The weakest of Sandler’s high-concept comedies feel like poorly written sketches stretched too thin. But Billy Madison manages to consistently surprise viewers with its bizarre plot twists and random jokes keeping it fresh and consistently funny.
9. Hotel Transylvania (2012): Sandler's Animated Monster Mash
Sandler has extended his wacky performances into animation. While his first animated film Eight Crazy Nights should be forgotten his second animated venture resulted in a popular family-friendly Halloween series. Hotel Transylvania was the first feature film directed by Genndy Tartakovsky an animation icon known for series like The Powerpuff Girls Dexter's Laboratory and Samurai Jack.
Tartakovsky's signature fast-paced style was a perfect match for Sandler’s over-the-top delivery as Dracula here portrayed as a goofy dad running a hotel exclusively for monsters. The visual jokes are rapid-fire and the classic monster characters are voiced by Sandler’s usual associates like Kevin James as Frankenstein. Sandler is well-suited to playing the madcap Drac and surprisingly adds some depth to the character's sad backstory.
10. The Waterboy (1998): Sandler's Man-Child Peak
Sandler was a reliable comedy hit-maker from the late 1990s into the 2000s. Though most of his films lacked critical acclaim they were popular with audiences. The formula often involved Sandler as a character often with a funny voice stuck in arrested development a man-child. The epitome of this character is Bobby Boucher the H2O-loving mama's boy in the college football comedy The Waterboy.
Sandler's second collaboration with director Frank Coraci The Waterboy relies on physical comedy and Sandler's penchant for broad character acting. In that context the movie surpasses Sandler's similar efforts in films like Little Nicky or Hubie Halloween. As Boucher Sandler is the ultimate underdog a simple man with an overprotective mother who discovers a talent for football when he releases years of suppressed anger. Added to this are hilarious supporting performances from Kathy Bates and Henry Winkler resulting in a silly comedy with just enough heart.
Adam Sandler's Enduring Appeal and Recent SNL Appearance
From Netflix Success to Red Carpet PDA with Wife Jackie
Adam Sandler's enduring presence was recently highlighted during the SNL 50th anniversary celebrations . He and his wife Jackie Sandler showed public affection at the SNL50: The Homecoming Concert event in New York City on February 14. Adam and Jackie shared a passionate kiss on the red carpet.
Adam dressed casually in a printed shirt dark jacket light-colored pants and sneakers while Jackie looked elegant in a black pantsuit. Later that evening Adam appeared onstage at the concert joined by former SNL cast members and other stars.
Adam and Jackie met on the set of Big Daddy in 1999 and married in 2003. They have two daughters Sadie and Sunny who both recently appeared with them in the 2023 Netflix film You Are So Not Invited to My Bat Mitzvah.
Adam rose to fame on SNL from 1990 to 1995. He recently guest-starred on a January episode hosted by Timothée Chalamet and in a December episode with Chris Rock. His SNL anniversary concert appearance came as the show celebrated its 50th season marked by a three-hour special broadcast. Sandler even jokingly mentioned ditching his signature basketball shorts for the special SNL event a nod to his casual style.
Adam Sandler's career showcases a fascinating blend of broad comedy and surprising dramatic depth. From early hits like Billy Madison and Happy Gilmore to acclaimed performances in Punch-Drunk Love and Uncut Gems Sandler has proven his versatility and staying power in Hollywood. His recent projects and public appearances confirm his continued relevance and appeal to audiences.