The romantic comedy is the cinematic equivalent of comfort food. The genre wraps us in its cozy blanket against a dreary world; a warm embrace when we're down on luck and love.
Almost every film in history combines some element of romance and comedy, but we made specific parameters to cull the list down to true rom-coms only. Not everyone will agree with certain omissions from the list, but this is our best attempt at categorizing something as abstract and widespread as the romantic comedy genre.
First and foremost, the central plotline in the rom-com has to be a romantic relationship. This eliminates, for example, Bridesmaids. The film is hilarious. And boasts a fantastic romance. But the blossoming love between Annie (Kristen Wiig) and her policeman hubby (Chris O'Dowd) is relegated to the B plot — her platonic relationships with Lillian (Maya Rudolph) and the other bridesmaids take center stage.
We also factored in tone when creating this list. Deciding whether a film's tone qualifies it for the romantic comedy genre is far more subjective. It's one of those "I'll know it when I see it" situations. Take Edward Scissorhands or Eternal Sunshine of the Spotless Mind. Both would fall apart without the romance at the center of the plot. And both mix in the occasional clever laugh. But neither has the lighthearted fluffiness, the high-key lighting, the montages of trying on clothes set to a pop song, or any of those things that make you say "Now that's a rom-com."
With these factors in mind, let's get into it. Here's our ranking of the best romantic comedies ever made.
25. How to Lose a Guy in Ten Days (2003)
Paramount Pictures
Benjamin Barry (Matthew McConaughey), aiming to prove his prowess in winning any woman's heart in order to land a big break at work, accepts a challenge to make a woman fall in love with him within ten days. Meanwhile, Andie Anderson (Kate Hudson), assigned to write a column on all the ways to drive a man away, selects Benjamin as her unwitting subject. This sets the stage for a delightful clash of intentions as the two inadvertently develop feelings for each other.
24. Friends With Benefits (2011)
CTMG, Inc.
Not to be confused with No Strings Attached, starring Natalie Portman and Ashton Kutcher (the other 2011 comedy about friends who also have sex sometimes and try to continue their arrangement without falling in love), Friends With Benefits stars Justin Timberlake and future Mrs. Kutcher Mila Kunis playing the pals who embark on the strictly physical romance. The film explores the challenges of compartmentalizing matters of the heart with plenty of charm, skepticism, and, finally, hope.
23. My Big Fat Greek Wedding (2002)
IFC Films
Toula is a Greek-American woman who feels stifled by the overwhelming traditions of her close-knit Greek family. However, her life takes an unexpected turn when she falls in love with Ian, a non-Greek schoolteacher. The ensuing narrative navigates the comic clashes between Ian's reserved upbringing and Toula's vibrant, tradition-rich family dynamics.
22. Crazy Rich Asians (2018)
Warner Bros. Pictures
When Rachel accompanies Nick to his best friend's wedding in Singapore, she discovers his incredibly wealthy and influential family, who are deeply enmeshed in traditional values and expectations. Not only is it a delightful romantic comedy, but it's also a cultural phenomenon that addresses issues of identity, social status, and the tension between individual desires and family obligations.
21. Set It Up (2018)
Treehouse Pictures
Harper (Zoey Deutch) and Charlie (Glen Powell) are two overworked and underappreciated assistants who devise a plan to set up their demanding and controlling bosses, played by Lucy Liu and Taye Diggs, in the hopes of gaining a bit more personal time. As they concoct elaborate schemes to bring their bosses together, the pair's own connection deepens in this heartwarming and deeply underrated examination of love in the modern workplace.
20. 10 Things I Hate About You (1999)
Getty Images
A modern adaptation of William Shakespeare's play "The Taming of the Shrew," set in a high school setting. The story revolves around the spirited and outspoken Kat Stratford (Julia Stiles) and her younger sister Bianca (Larisa Oleynik). Their overprotective father enforces a rule that Bianca can only date if Kat does. Enter Patrick Verona (Heath Ledger), a rebellious but charming young man who is offered money to woo Kat and pave the way for Bianca's romantic pursuits.
19. Palm Springs (2020)
Hulu
Comedy, sci-fi, and love intermingle in this film starring Andy Samberg and Cristin Milioti. Nyles (Samberg) and Sarah (Milioti) are two wedding guests who find themselves trapped in a time loop, reliving the same day over and over again. As they navigate the repetitious existence and come to terms with their predicament, their initial antagonism evolves into a deep bond.
18. Silver Linings Playbook (2012)
The Weinstein Company
Pat Solitano (Bradley Cooper) is a man with bipolar disorder who has recently been released from a mental health institution after a violent incident. He is determined to get his life back on track and win back his estranged wife, despite her having obtained a restraining order against him. As Pat tries to rebuild his life, he meets Tiffany (Jennifer Lawrence), a young woman dealing with the death of her husband. Tiffany offers to help Pat reconnect with his wife in exchange for his participation in a dance competition, and the two form an unlikely bond.
17. The Apartment (1960)
The Mirisch Company
A classic of the genre that has left a lasting impact. To get a leg-up on his career, C.C. Baxter lends out his apartment to his superiors for their extramarital affairs. But his plans become complicated when he develops feelings for Fran Kubelik, an elevator operator who is romantically involved with his boss.
16. Clueless (1995)
CBS Photo Archive
An adaptation of Jane Austen's novel Emma set in a Beverly Hills high school during the 1990s. Cher Horowitz (Alicia Silverstone) is a wealthy and popular high school student who sees herself as a matchmaker and fashionista. Her comedic and often ill-fated attempts at sparking romance for others leads her to overlook a romance of her own with her former stepbrother Josh (Paul Rudd).
15. Bridget Jones's Diary (2001)
Miramax Films
Based on Helen Fielding's novel of the same name and known as a modern-day reinterpretation of Jane Austen's Pride and Prejudice, the film follows Bridget Jones (Renée Zellweger), a single, thirty-something woman living in London who is determined to improve her life. Bridget's journey is chronicled through her diary entries, where she candidly writes about her struggles with weight, career aspirations, and most importantly, her romantic pursuits, namely, her escapades with two very different men: her charming but unreliable boss, Daniel Cleaver (Hugh Grant), and the seemingly standoffish but ultimately kind-hearted Mark Darcy (Colin Firth).
14. Moonstruck (1987)
MGM
Set in an Italian-American community in Brooklyn, the widowed Loretta Castorini (Cher) agrees to marry her boyfriend Johnny Cammareri (Danny Aiello) despite not being passionately in love with him. However, complications arise when Loretta meets Johnny's estranged brother Ronny (Nicolas Cage), and sparks fly between them.
13. There's Something About Mary (1998)
Twentieth Century Fox
Ted Stroehmann (Ben Stiller) has been in love with his high school crush, Mary (Cameron Diaz) for years, but has lost touch with her since an excruciatingly cringe-inducing prom night mishap. As he embarks on a journey to win her heart, the film is marked by over-the-top humor, physical comedy, and a parade of Mary's eccentric suitors.
12. Pretty Woman (1990)
Getty Images
This Cinderella story follows Vivian Ward (Julia Roberts), a charismatic and street-smart sex worker in Los Angeles. Edward Lewis (Richard Gere), a wealthy businessman, hires Vivian for a week to accompany him to various events and functions. As the two spend time together, their initial differences start to dissolve.
11. Sleepless in Seattle (1993)
TriStar Pictures
Sam Baldwin (Tom Hanks) is a recently widowed architect struggling to move on from the loss of his wife. His young son Jonah calls into a late-night radio talk show to share his father's story, and the call reaches the ears of Annie Reed (Meg Ryan), a journalist in Baltimore. Annie becomes captivated by Sam's story and believes he might be the man of her dreams. This iconic tale of long-distance romance has made the film's title synonymous with the idea of being unable to sleep due to romantic longing and, in many ways, predicted the future of dating.
10. Groundhog Day (1993)
Sony Pictures Home Entertainment
Cynical and self-absorbed weatherman Phil Connors (Bill Murray) finds himself trapped in a time loop, repeating the same day—Groundhog Day—over and over again in the small town of Punxsutawney. He first uses the opportunity to engage in all manners of hedonistic activity before deciding to use his unlimited do-overs to perfect the art of wooing his dream girl, Rita (Andie MacDowell).
9. 500 Days of Summer (2009)
Fox Searchlight Pictures
Greeting card writer Tom Hansen (Joseph Gordon-Levitt) falls head over heels for his co-worker Summer Finn (Zooey Deschanel). The film is divided into 500 days, jumping back and forth in time to various moments in Tom and Summer's relationship, and made the "manic pixie dream girl" a trope of the late 2000s.
8. To All the Boys I've Loved Before (2018)
Netflix
High school junior Lara Jean Covey (Lana Condor) writes secret love letters to all of her past crushes but never intends to send them. However, her world is turned upside down when the letters are accidentally sent out, revealing her innermost feelings to her former crushes, including her sister's ex-boyfriend Josh (Israel Broussard) and popular jock Peter Kavinsky (Noah Centineo).
7. Bros (2022)
Universal Studios
Bobby (Billy Eichner) is a neurotic podcast host who settles for ultimately awkward and unfulfilling Grindr hookups instead of committing to a loving relationship. But that all changes when he crosses paths with the equally non-committal Aaron (Luke Macfarlane). It's a hilarious look at an LGBTQ+ dating scene lacking in accurate modern portrayals and a heartfelt and passionate revelry of the community's progress — and it throws a caustic side-eye at those who continue to deny its acceptance.
6. Say Anything (1989)
20th Century Fox Home Entertainment
A realistic portrayal of young love and a zeitgeist-definer for Gen Xers. The story centers around Lloyd Dobler (John Cusack), an optimistic and unconventional high school graduate, who falls in love with Diane Court (Ione Skye), the class valedictorian and aspiring scholar. Despite their differing backgrounds, Lloyd's laid-back attitude, and Diane's overprotective father's disapproval, they embark on a tender and passionate romance during the summer before college.
5. The Big Sick (2017)
WHILE YOU WERE COMATOSE, LLC
The film is based on the real-life love story of Kumail Nanjiani (who also stars in the film) and Emily V. Gordon, who co-wrote the screenplay. The story follows Kumail, a Pakistani-American comedian and aspiring stand-up, who meets Emily (Zoe Kazan), an American grad student, at one of his comedy shows. Their relationship blossoms, but complications arise due to Kumail's traditional Muslim family's expectations of an arranged marriage. When Emily falls seriously ill and is placed in a medically induced coma, Kumail finds himself spending time with her parents, played by Ray Romano and Holly Hunter, with whom he forges a unique and personal bond.
4. Bull Durham (1988)
Metro-Goldwyn-Mayer Studios Inc.
Equal parts rom-com and sports film, the story follows Crash Davis (Kevin Costner), a veteran catcher who is assigned to mentor a talented but raw rookie pitcher named "Nuke" LaLoosh (Tim Robbins) in the minor leagues. The team also attracts the attention of Annie Savoy (Susan Sarandon), a passionate baseball fan who engages in a unique ritual of choosing a new player each season to have a romantic affair with.
3. Annie Hall (1977)
Bettmann
One of Woody Allen's most iconic works, the film is anchored by Alvy Singer (Allen), an overanxious comedian, and his tumultuous relationship with the free-spirited and quirky Annie Hall (Diane Keaton). Through a non-linear narrative, Alvy reflects on his past relationships, his experiences with Annie, and the reasons for their breakup.
2. Four Weddings and a Funeral (1994)
Metro-Goldwyn-Mayer Studios Inc.
A British bachelor named Charles (Hugh Grant) frequently attends weddings but struggles to find lasting love himself. Over the course of several years, the film takes viewers through four weddings and, as the title suggests, one funeral. Throughout these events, Charles reconnects with Carrie (Andie MacDowell), an American woman with whom he shares a series of missed opportunities and chance encounters. Hugh Grant is considered the King of Rom-Coms and this is largely regarded as his best role in the genre.
1. When Harry Met Sally... (1989)
Twentieth Century Fox
Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) meet as recent college graduates on a road trip from Chicago to New York. Over the course of several years, they cross paths multiple times, each encounter revealing their evolving views on love. The film features some of the most iconic and riotous scenes in film history, most notably when Sally demonstrates in the middle of a crowded diner how well women can fake an orgasm, to which another customer famously replies, "I'll have what she's having." In addition to the humor, the film is celebrated for its poignant and realistic examination of the nuances of male-female relationships.
