Adam Sandler has proven to have quite a bit of range in his acting. For decades he’s made his mark in different areas of the entertainment biz, from his early days in standup comedy and Saturday Night Live to dramatic endeavors like Uncut Gems and Hustle (which is one of the best sports movies on Netflix right now), and even family friendly projects like You Are So Not Invited to My Bat Mitzvah and Leo. But another genre that the Sandman can claim mastery in is romantic comedy, and we’ve compiled a list of Sandler's standouts among the best rom-coms of all time.
Adam Sandler’s name pops up quite a few times in the world of romantic comedies, so regardless of if you think Drew Barrymore or Jennifer Aniston is the better love interest for him, there’s simply no denying that he has the charisma to capture audiences’ hearts. Below are Sandler’s 9 best romantic comedies, ranked from worst to best.
9. Blended (2014)
When you think of the most iconic rom-com partners, Meg Ryan and Tom Hanks come to mind, as well as Julia Roberts and Richard Gere. Adam Sandler and Drew Barrymore undoubtedly belong in that conversation as well. Blended is the third (and most recent) of their romantic comedies — unless they decide to make another movie together — which sees single parents Jim and Lauren decide not to see each other again after an unsuccessful blind date. However, those plans go out the window when they end up staying with their respective children at the same African safari resort.
Rent or buy Blended on Amazon Prime Video.
8. Just Go With It (2011)
It’s Adam Sandler’s charm, as well as his chemistry with Jennifer Aniston, that make Just Go With It enjoyable despite a morally deficient premise. Sandler plays Danny, a plastic surgeon who pretends to be in an unhappy marriage in order to attract the sympathies of women. However, when he meets Palmer (Brooklyn Decker), he wants to end the ruse, and he enlists the help of his assistant Katherine (Aniston), convincing her to pretend to be the wife who is divorcing him. Somehow things don’t go quite according to plan.
Stream Just Go With It on Starz.
Rent or buy Just Go With It on Amazon Prime Video.
7. Mr. Deeds (2002)
Not quite your traditional romantic comedy, Mr. Deeds still fits the bill with its romance being a central story amidst the absurdity. Adam Sandler’s Longfellow Deeds goes from a beloved owner of a pizzeria to an instant multi-billionaire after the death of a distant uncle. As he sets about using his new fortune to help improve the lives of others, he falls for Babe Bennet (Winona Ryder), an opportunistic reporter posing as school nurse Pam Dawson. While not loved by critics, Sandler still sells this early-aughts flick, which includes the obligatory grand gesture to seal its romance.
Rent or buy Mr. Deeds on Amazon Prime Video.
6. Spanglish (2004)
There were several signs earlier in Adam Sandler’s career that he was capable of more than manchild, sophomoric humor, and Spanglish was one of those. The story centers around Flor (Paz Vega), a single mother who moves from Mexico to Los Angeles in search of a better life. Despite a language barrier, she begins housekeeping for the Claskys, ultimately forming a bond with John (Sandler). Despite bombing at the box office, Spanglish received praise for Sandler and Vega’s performances.
Rent or buy Spanglish on Amazon Prime Video.
5. Big Daddy (1999)
While certainly capable of more dramatic roles, Adam Sandler may have shined the brightest in his decidedly unserious roles of the ‘90s, as proven by Big Daddy, which was 1999’s seventh highest-grossing movie domestically (and 12th worldwide, per Box Office Mojo). The Sandman plays Sonny, a thirtysomething slacker who decides that caring for his out-of-town roommate’s 5-year-old son Julian (Cole and Dylan Sprouse) is the best way to win back his ex-girlfriend. The joke’s on Sonny, as he actually does grow up, bonding with Julian, and becoming emotionally mature enough to engage in a new and healthy relationship with Layla (Joey Lauren Adams).
Rent or buy Big Daddy on Amazon Prime Video.
4. Billy Madison (1995)
While it contains many of Adam Sandler’s funniest movie quotes, Billy Madison is not considered a rom-com by everyone’s standards. However, the relationship plot here is more in the forefront than some of his other comedies and therefore deserves a place on this list. Sandler stars as the titular character, who must repeat kindergarten through 12th grade in order to prove he’s smart enough to inherit his father’s chain of hotels. Billy ends up falling for third-grade teacher Veronica Vaughn (Bridgette Wilson), who rebuffs him at first but then becomes integral to keeping him on the right track when others try to derail him.
Stream Billy Madison on Starz.
Rent or buy Billy Madison on Amazon Prime Video.
3. 50 First Dates (2004)
In 50 First Dates — the second joint venture of Adam Sandler and Drew Barrymore — Sandler plays commitment-phobic Henry, who decides to change his womanizing ways after spending a perfect day with Barrymore’s Lucy. However, he soon learns that due to a terrible car accident, Lucy loses her memory each night when she goes to sleep, effectively living the same day over and over. Henry shows incredible tenderness, patience and determination in the lengths he goes to make their relationship work day after day, making this one of Sandler’s best. Not to mention, 50 First Dates’ ending is one we’re still contemplating all these years later.
Stream 50 First Dates on Starz.
Rent or buy 50 First Dates on Amazon Prime Video.
2. Punch-Drunk Love (2002)
Punch-Drunk Love is possibly our earliest indication that the comedian would be great in a dramatic role, as Adam Sandler plays Barry, a troubled and socially awkward man who falls for one of his seven sisters’ co-workers, Lena (Emily Watson). In true Paul Thomas Anderson fashion, the comedy is dark in its exploration of loneliness and the unfolding of an unconventional love story, but the humor is there nonetheless with a charming and critically acclaimed performance from Sandler. Decades later, many consider Punch-Drunk Love to be one of the actor’s best movies.
Rent or buy Punch-Drunk Love on Amazon Prime Video.
1. The Wedding Singer (1998)
Adam Sandler’s first movie with Drew Barrymore — The Wedding Singer — is widely considered the best of their three, and one of the best movies of the ‘90s overall. Set unmistakably and hilariously in the 1980s, the heartbroken wedding singer Robbie Hart (Sandler) strikes up a friendship with a waitress, Julia (Barrymore), who is planning her own wedding. Their attraction becomes undeniable, culminating in the grandest of grand gestures on an airplane with the help of passengers, the flight crew and Billy Idol (naturally).
Rent or buy The Wedding Singer on Amazon Prime Video.
Adam Sandler’s career has taken him in a lot of different directions, genre-wise, and lucky for us, Hollywood learned early on how well his authenticity and humor lended themselves to leading roles in romantic comedies.
