Adam Sandler's 14 Best Roles Ranked

Adam Sandler has had a fascinating career. Beginning with his star-making role as a cast member on "Saturday Night Live," Sandler's early time in the spotlight was defined by baby talk, sing-songy jokes, and goofy yelling. Early on, Sandler primarily played overgrown and over-privileged man babies with hair-trigger tempers. Many of those performances are very, very funny, but they don't come with a particularly large amount of depth.

However, as Sandler has grown as an actor (particularly after leaving "Saturday Night Live" and becoming a fully-fledged movie star), he has taken on more dramatic acting roles, leading to critical acclaim and attention. Not that he doesn't still make comedies, of course; the whiplash you'll get looking at Sandler's filmography is almost overwhelming. Still, Sandler's overall film career is as varied as the performer himself. These are his 14 best roles, ranked from worst to best.

14. Bobby Boucher — The Waterboy

In addition to his comedic persona, Sandler is known for making high-concept comedies. One example of this is "The Waterboy" which follows Bobby Boucher, a waterboy for a college football team who lives with his overprotective and disapproving mother (Kathy Bates). While the players mock Bobby for his strong Cajun accent and sincere love of water, things change when Bobby's talent for tackling is accidentally shown during practice and Bobby gets promoted from waterboy to teammate. 

Though his mother doesn't approve of football, Bobby slowly gains his independence and discovers a new side of himself, attaining both education and a girlfriend. While "The Waterboy" was released during Sandler's prime, only three years after his departure from "Saturday Night Live," it features all the worst of Sandler's tendencies as a performer meshed into one character, making Bobby a character that wears thin a little faster than some of his others, and leaving "The Waterboy" ranked last on our list.

13. Danny — Just Go With It

One of the later-era Sandler comedies, "Just Go With It" features an even more convoluted plot than Sandler's earlier films. In "Just Go With It," Sandler stars as Danny, a plastic surgeon who was left at the altar when he was younger and now uses his wedding ring to pick up women. Things get complicated when he meets Palmer (Brooklyn Decker), a woman he wants to spend more than one night with. As a result, he asks his faithful assistant, Katherine (Jennifer Aniston) to pose as his ex-wife. As Danny and Palmer grow closer, the lies get more ridiculous, including that Katherine's kids are also Danny's, leading to a family vacation in Hawaii with Danny, Palmer, Katherine and her children.

While the trip is intended to show Palmer that Katherine is okay with Danny moving on, the fake relationship begins to feel more real. Throughout the trip, Danny and Katherine grow closer and realize they have feelings for each other beyond friendship. Sandler and Aniston have great chemistry and strong banter, but at times, his performance is a bit cold. Though Sandler is funny, his performance lacks some of the heart and charm of his more nuanced roles, leaving it near the bottom of our list.

12. Longfellow Deeds — Mr. Deeds

A remake of the 1936 Frank Capra film "Mr. Deeds Goes to Town," Sandler stars as the eponymous Mr. Deeds, a naïve small-town guy who dreams of writing greeting cards for Hallmark. Deeds' life turns upside down when he inherits a massive fortune from his unknown billionaire uncle. With the national spotlight on him as the heir to his uncle's media conglomerate, Deeds has to move to the Big Apple and step into his uncle's shoes while avoiding constant media attention. 

As a hometown hero, Deeds is not incredibly worldly, which leads to him falling in love with an undercover reporter going by Pam (Winona Ryder). As they get closer, the fake relationship becomes more real and Pam begins to feel more conflicted about her lies. On the whole, Sandler does a good job at playing a trusting but intelligent man, but "Mr. Deeds" lacks some of the humor and heart of his best performances.

11. Henry Roth — 50 First Dates

Like Meg Ryan and Tom Hanks before them, Adam Sandler and Drew Barrymore's romantic comedy pairings stand as a sort of unofficial cinematic universe. The second in the Adam Sandler-Drew Barrymore trilogy, "50 First Dates," follows Henry Roth, a veterinarian at an aquarium in Hawaii who passes his time romancing tourists until he meets an art teacher named Lucy (Barrymore) in a local restaurant. The two hit it off immediately and agree to have breakfast the next day, but when Henry shows up, Lucy doesn't remember meeting him. 

The restaurant owner tells Henry that Lucy has a rare form of amnesia due to a car accident, and only remembers the day of her injury. While Lucy manages to break through Henry's desire to only date tourists, Henry has to prove himself to Lucy's friends and family while also creating new ways to introduce himself to her. Though the premise hasn't aged well, reuniting with Barrymore is a winner for Sandler, who charms as a romantic lead and manages to rein in many of his wilder impulses for a more grounded and charming performance.

10. Jim — Blended

The third entry in the Sandler-Barrymore trilogy, "Blended" follows Sandler as Jim, a widowed father of three girls who ends up on a blind date with Drew Barrymore's Lauren, a divorced mother of two boys. You might be able to guess where this "Brady Bunch"-esque story is headed, except that Jim and Lauren's first date goes horribly wrong in every way imaginable. Of course, life continues to throw them together until they wind up (again, through convoluted Sandler-ian means) on the same family vacation in South Africa.

While Jim and Lauren clash on many superficial fronts initially, they both have in common a deep and sincere love for their children, which Sandler portrays with an overall earnest bent. As they get to know each other — and each other's kids — they grow closer and begin to imagine new futures for themselves and their families. While the film itself belongs on the sillier end of Sandler's canon, his performance as a heartbroken widower and protective father overall feels surprisingly grounded and emotional. As always, Sandler's winning chemistry with Barrymore is a recipe for success.

9. Sandy Koufax — Big Daddy

Continuing the trend of casting adorable kids opposite the curmudgeonly Sandler, "Big Daddy" follows the comedian as Sandy Koufax, a former lawyer who lives off a settlement he won early in his career. Sandy is aimless and using the money to avoid adulthood and reality, which leads his girlfriend to break up with him. Meanwhile, Sandy's friend, Kevin (Jon Stewart), has a long lost and unknown son who surfaces when Kevin is out of town, leading Sandy to pose as Kevin and become a foster father to the young boy in order to prove his maturity to his ex-girlfriend.

Of course, the rash decision means that Sandy is anything but ready to be a father, leading him to teach the five-year-old Julian how to behave like an adult more than a child. As the film progresses, Sandy and Julian grow closer even as the reality of the situation looms large. While the film is incredibly goofy and Sandy is a character that can be a bit difficult to relate to, Sandler manages to find moments of honesty and real emotion as he starts to care about Julian, giving us early glimpses of the dramatic performer he would later become.

8. Billy — Billy Madison

As his first breakout film role, "Billy Madison" may go down as Sandler's most iconic character. A spoiled rich kid, Billy wants for nothing in life, and nothing is expected of him. However, when he learns his father's company is going to be handed over to his dad's smarmy employee Eric (Bradley Whitford), Billy decides that he's ready to step up and try to be an adult. Of course, in a very silly turn of events, Billy can only inherit the company if he proves to Eric and his father that he's taking it seriously by going back to school.

With the task of repeating first through twelfth grade in a matter of weeks to win the bet, Sandler is primed for lots of ridiculous hijinks, and his childish humor shines opposite the numerous straight-faced children. "Billy Madison" is Sandler at his Sandler-iest: incredibly goofy, silly, and full of hilarious gibberish. At times sarcastic and mean, Sandler manages to maintain a level of charm that keeps Billy endearing throughout and begins Sandler's legacy of winning performances alongside child actors.

7. Happy — Happy Gilmore

Part of the early Adam Sandler canon and easily one of his most famous roles, "Happy Gilmore" follows Sandler as the eponymous Happy, a wannabe professional hockey player who unfortunately isn't very good at the sport. However, Happy has lots of anger issues, and hockey is one of the only ways for him to channel his emotions. That is, until he accidentally discovers golf — and his talent for it. Happy's constant, barely controlled rage allows him to drive the ball and attracts media attention, leading him to gain a fresh nemesis, the incumbent champion Shooter McGavin (Christopher McDonald).

While Happy is outwardly angry, his grandmother, who raised him, is his anchor and emotional support, so Happy reluctantly becomes a golfer in order to save her house when it goes under foreclosure. As Happy skyrockets to fame, the pressure mounts to win the tournament and save his grandmother's house while outwitting Shooter. If "Billy Madison" spotlights Sandler's childishness, "Happy Gilmore" showcases his penchant for yelling and rage. While his performance lacks the emotional nuance of Sandler's later roles, Happy is a more grounded character with a pure motivation that makes him both relatable and timeless.

6. Robbie Hart — The Wedding Singer

The first and strongest of the Sandler-Barrymore trilogy and the best of the classic Sandler era of films, "The Wedding Singer" follows Sandler's Robbie Hart, a struggling wedding singer in 1985. A trope that Sandler's films later lean on, Robbie is left at the altar, but despite his heartbreak has to continue performing. When Robbie meets Julia (Drew Barrymore), a cater-waiter, they become fast friends, and he offers his expertise to help her plan her wedding. However, Robbie quickly falls for Julia, and tries to determine if she's really in love with her jerk of a fiancé, Glenn.

As the wedding date approaches, it's clear that Julia is with the wrong guy, but neither she nor Robbie know what to do. While many of Sandler's early movies have a romantic subplot, "The Wedding Singer" feels like his most straightforward romantic comedy in structure and execution, and showcases Sandler's ability to play more serious parts. In "The Wedding Singer," Sandler finds the exact right mix of charm, sarcasm, and self-deprecation, making him a winning romantic lead opposite Barrymore.

5. John Clasky — Spanglish

Written and directed by Hollywood legend James L. Brooks, "Spanglish" follows the story of a mother, Flor (Paz Vega), and her daughter, who immigrate to California from Mexico. The film examines Flor's struggle to protect her daughter when she begins working for the Claskys, a wealthy white family, as their lives become increasingly entangled. Sandler plays John, the Clasky patriarch and a renowned chef whose wife is at once manic and cold and entirely distant from her husband. As John and Flor grow closer, things get more complicated for their respective families.

"Spanglish" is the first entry on our list that's a departure from Sandler's traditional brand of comedy, as he began to shift into more dramatic roles at this point in his career. Sandler delivers a gentle and nuanced performance with only occasional flashes of his trademark, goofy yelling. While he handles the film's romance with his classic charm, Sandler particularly excels in his role as a father, at turns heartbroken and loving.

4. George Simmons — Funny People

Judd Apatow's tribute to standup comedy, "Funny People" follows a not-so-subtle fictional version of Sandler named George Simmons. Simmons is a rich and famous comedian who has everything he could ever want except family, friends ... and his health. At the beginning of the film, George receives a terminal cancer diagnosis that sends him back to his first and one true love, stand-up comedy. While he basically bombs, Ira Wright (Seth Rogen) goes up after him, leading the two to connect as George hires Ira to be his assistant and joke writer.

As George navigates his health crisis, he continues to look back on the "what if" moments in his life and reconnects with his long lost love, Laura (Leslie Mann), who is now married with children. As the two grow closer, Ira has to decide whether to intervene and protect George or potentially risk their friendship. Apatow wrote the part specifically for Sandler, his former roommate, and it works well; the film uses Apatow's old footage of Sandler throughout and incorporates their inside jokes to make the character feel much more lived in. Overall, perhaps due to his closeness to the material, Sandler imbues George with a sense of grief and ennui, even as his dry sarcasm brims on the surface.

3. Danny — The Meyerowitz Stories

Regardless of whether it's a comedic or dramatic role, Sandler's best performances are those that are grounded and natural. Writer-director Noah Baumbach and Sandler make an excellent pair as a result. In "The Meyerowitz Stories," Sandler plays Danny, the eldest son of a narcissistic but undiscovered sculptor named Harold (Dustin Hoffman). After Danny gets separated and sends his own child off to college, he comes back home to spend time with his dad and works with his sister Jean (Elizabeth Marvel) to organize a retrospective art show for their father's work.

As the art show approaches, a family crisis brings them all together, including the youngest and favorite son, Matt (Ben Stiller). The film mostly follows the family dynamics of the siblings in relation to their father, and due to its naturalistic style features lots of drier comedic moments. It seems like a role Sandler couldn't have played when he was younger, both because of the emotional subtlety and the life experience required. Regardless, Sandler turns in one of the best performances of his career.

2. Barry Egan — Punch-Drunk Love

Considered to be Sandler's breakout dramatic acting role, Paul Thomas Anderson's "Punch-Drunk Love" is a peculiar and intimate character study centered on Sandler's Barry Egan, a depressed and anxious salesman with numerous eccentricities. Barry is a lonely guy who spends most of his time buying excessive amounts of pudding as part of a Healthy Choice scheme to earn frequent flier miles. Barry's world collapses when, in a moment of extreme loneliness, he calls a phone sex line and is then blackmailed by the sex worker the next day.

As Barry tries to ignore it, he meets a new, real woman, Lena (Emily Watson), who likes Barry despite his anger issues and tenuous relationship with reality. Sandler's performance earned him his first (and to date only) Golden Globe nomination and much critical acclaim. On the whole, his performance is nuanced and grounded and adds a new facet to his anger and emotional range.

1. Howard Ratner — Uncut Gems

The most recent film on our list also wins the top spot. An older Sandler is at home in "Uncut Gems" as Howard Ratner, a jewelry dealer and gambling addict working to repay his debts. Upon the receipt of a rare and raw opal, Howard believes all of his financial problems will be solved and his debts can be repaid, but keeps digging himself deeper by placing new bets to try to make more money. The situation grows more complicated when NBA star Kevin Garnett comes to his jewelry store and falls in love with the opal, which is already set for auction. 

Sandler's generally unhinged personal works well as the centerpiece of "Uncut Gems," a twisty and suspenseful gut punch of anxiety brimming with immediacy and tension. His performance could easily feel like a shtick with his tracksuit, goatee, gold chains, and tinted glasses. However, Sandler manages to utilize the more grating parts of his comedic persona to incredible dramatic effect, making Howard the best role of his career — at least so far.