Adam Sandler’s romantic comedies have entertained audiences for decades, spanning from iconic late ’90s hits to more recent Netflix releases. This ranking covers each of his rom-coms, evaluating which films succeed with charm and which fail to deliver, highlighting the varied appeal of Adam Sandler romantic comedies ranking.
From beloved cult classics like The Wedding Singer to newer releases such as Murder Mystery, Sandler’s rom-coms display a range of humor and emotional depth, creating a unique legacy within the genre.
The Least Favored: Films That Miss the Mark
11. The Do-Over (2016)
In this action-romantic comedy blend, Adam Sandler teams up with David Spade as two friends who fake their deaths to start fresh lives. Despite the premise, the romantic aspect is barely present, with the film focusing more on absurd action sequences and lacking emotional sincerity. Even the humor struggles to land effectively.
Streaming: Now available on Netflix.
10. Just Go With It (2011)
Featuring Sandler as a plastic surgeon who convinces his assistant, played by Jennifer Aniston, to impersonate his soon-to-be-divorced wife, this film revolves around deception and awkward scenarios. Though Sandler and Aniston share some chemistry, the storyline feels forced and drawn out, saying little beyond its surface charm.
Streaming: Available for rent on Prime Video and AppleTV.
9. Blended (2014)
Reuniting Adam Sandler with Drew Barrymore, this rom-com centers on two single parents whose families collide during a vacation. While the stars exhibit warm on-screen chemistry, the movie relies heavily on slapstick comedy and occasionally awkward plot developments that weaken its appeal.
Streaming: Available for rent on Prime Video and AppleTV.
Mixed Reactions: Films With Some Merit But Flaws
8. Murder Mystery (2019)
Netflix pairs Sandler again with Jennifer Aniston in this comedic tale of a couple entangled in a European murder investigation. More of a thriller with comedic elements than a typical romantic comedy, the mystery overshadows the romance, making the film less emotionally compelling despite the couple’s playful interactions. It also has a sequel, Murder Mystery 2 (2023).
Streaming: Available now on Netflix.
7. I Now Pronounce You Chuck & Larry (2007)
Starring Adam Sandler and Kevin James as firefighters pretending to be a gay couple to claim partner benefits, this film has not aged well, with some humor now considered offensive. Nonetheless, the movie attempts to deliver a message about love and acceptance, balancing humor with a degree of sincerity.
Streaming: Rentable on Prime Video and AppleTV.
6. The Week Of (2018)
Featuring Chris Rock, Rachel Dratch, and Jim Barone alongside Sandler, this film focuses on the chaos surrounding a father organizing his daughter’s wedding. Although it’s not a conventional romantic comedy, the themes of love and family, combined with a slower, more heartfelt pace, set it apart within Sandler’s work.
Streaming: Available for streaming on Netflix.
Noteworthy but Underrated: Films That Showcase Depth and Range
5. Spanglish (2004)
Despite mixed critical reception, Spanglish has gained a devoted fan base. Sandler portrays a chef navigating a challenging marriage, but the emotional core centers on his connection with a housekeeper, played by Paz Vega. This film highlights his ability to blend bittersweet romance with subtle humor, making it one of his more realistic and touching roles.
Streaming: Available to rent on Prime Video and AppleTV.
4. Punch-Drunk Love (2002)
Directed by Paul Thomas Anderson, this film is a departure from traditional romantic comedies. Sandler plays Barry, a socially awkward man who battles anxiety and anger while finding unexpected love. Quirky and artistic, it offers a glimpse of Sandler’s vulnerability and dramatic range, creating a unique romantic story.
Streaming: Available to rent on Prime Video and AppleTV.
The More Popular Choices: Films Blending Comedy and Romance Effectively
3. Big Daddy (1999)
A major early hit for Sandler, Big Daddy centers on Sonny Koufax, who unexpectedly becomes a caretaker for a child and experiences personal growth. The romantic subplot with Layla (Joey Lauren Adams) is heartfelt but subtle, making the film more about maturation than romance, packaged in Sandler’s signature goofy humor.
Streaming: Rentable on Prime Video and AppleTV.
2. 50 First Dates (2004)
One of Sandler’s most cherished films, this movie pairs him with Drew Barrymore as Henry, a man pursuing Lucy, a woman with short-term memory loss. The fresh and sweet concept tugs at the heartstrings, though some revisit it with mixed feelings due to ethical concerns about the character dynamics. Nevertheless, their chemistry makes it a memorable romantic comedy.
Streaming: Available to rent on Prime Video and AppleTV.
The Timeless Classic: The Best of Adam Sandler’s Rom-Coms
1. The Wedding Singer (1998)
This fan-favorite features Sandler as Robbie, a wedding singer left at the altar who discovers love with Julia, a waitress engaged to another man. Set in the ’80s, the film combines humor and heartfelt moments with exceptional Sandler-Barrymore chemistry. It is celebrated for balancing comedy and emotional warmth, standing as a peak example of Sandler’s franchised romantic comedies.
Streaming: Available for rent on Prime Video and AppleTV.
Audience Interaction and Future Outlook
With this ranking complete, fans are encouraged to share their favorite Adam Sandler romantic comedies and join the conversation on which films resonate most. As Sandler continues to blend romance with comedy across new projects, the enduring appeal of his rom-coms is likely to remain a topic of lively discussion among viewers.
