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Every Valentine's Day, critics of romantic comedies emerge, dismissing the genre as repetitive or unrealistic. However, true rom-com enthusiasts know that these films offer a diverse spectrum of storytelling, from sharp wit to lighthearted charm. If you haven't found a rom-com you love, it's likely because you haven't found the right one yet. To help you out, we've compiled a list of 20 exceptional romantic comedies, perfect for both fans and skeptics, just in time for Valentine's Day.
1. It Happened One Night (1934)
Frank Capra, a legendary filmmaker, gifted us this timeless romantic comedy that remains a gold standard for odd-couple love stories. What stands out about It Happened One Night is its simplicity compared to modern rom-coms. Claudette Colbert and Clark Gable shine in intimate, unadorned settings, whether sharing a small room or hitchhiking on a roadside. Their chemistry makes this nearly century-old film a must-watch even today.
2. Ninotchka (1939)
While Greta Garbo is often remembered for her aloof demeanor, director Ernst Lubitsch brilliantly showcased her versatility in Ninotchka. The film tells the story of a stern Russian envoy (Garbo) who learns to embrace life's joys through her interactions with a charming nobleman (Melvyn Douglas). Despite its dated critique of pre-WWII Communism, the film's comedic moments, especially Garbo and Douglas's drunken escapades, remain timeless and endearing.
3. The Philadelphia Story (1940)
A masterpiece from George Cukor, The Philadelphia Story highlights the unparalleled talent of Katharine Hepburn. Playing a socialite torn between Cary Grant and Jimmy Stewart, Hepburn delivers a performance that outshines even these legendary actors. The film is a perfect blend of wit and charm, with unforgettable scenes like Stewart's drunken serenade while carrying Hepburn.
4. His Girl Friday (1940)
His Girl Friday stands out as one of the greatest workplace and reconciliation romances, largely due to the electric chemistry between Cary Grant and Rosalind Russell. Howard Hawks's iconic film is celebrated for its rapid-fire, overlapping dialogue, a groundbreaking technique at the time. However, what truly makes it a timeless romantic comedy is the undeniable spark between Grant and Russell. Their playful banter and intellectual rivalry, combined with their enthusiasm for the script's eccentricities, elevate the film to legendary status.
5. Roman Holiday (1953)
As the quintessential fairy tale romantic comedy, Roman Holiday captures the essence of a destination rom-com with its enchanting blend of star power, stunning locales, and William Wyler's masterful direction. Audrey Hepburn shines as a princess seeking a day of normalcy in Rome, while Gregory Peck's charisma and charm infuse the film with a sense of adventure and wonder that resonates with anyone who has ever dreamed of escaping their everyday life.
6. Desk Set (1957)
Katharine Hepburn and Spencer Tracy's legendary chemistry reaches its romantic comedy peak in Desk Set, a delightful enemies-to-lovers story. Directed by Walter Lang and penned by Phoebe and Henry Ephron, the film follows a brilliant research librarian (Hepburn) and an efficiency expert (Tracy) who initially aims to replace her with a computer but soon realizes her irreplaceable value. The rooftop lunch scene, where Tracy's character interrogates Hepburn in the freezing cold, is a standout moment of rom-com brilliance.
7.
The Apartment (1960)
Billy Wilder, often hailed as a pioneer of modern romantic comedies, delivered his magnum opus with The Apartment. While Some Like It Hot garners more attention, this film stands out for its nuanced, darker tone. Jack Lemmon and Shirley MacLaine bring depth and charm to Wilder and I.A.L. Diamond's understated script, creating a bittersweet yet vibrant narrative. The film's honest portrayal of love, coupled with iconic moments like Lemmon using a tennis racket to strain spaghetti, cements its place as a rom-com classic.
8. Some Kind of Wonderful (1987)
John Hughes, a master of teen comedies, is often celebrated for Pretty In Pink and Sixteen Candles. However, Some Kind of Wonderful, his later collaboration with director Howard Deutch, offers a more refined take on teen romance. This film revisits class-divide themes but with greater depth, presenting a realistic high school love story rather than a fairy tale. The compelling performances of Eric Stoltz, Lea Thompson, and Mary Stuart Masterson create one of cinema's most underrated love triangles.
9. Moonstruck (1987)
Norman Jewison and John Patrick Shanley's Moonstruck has become a cultural touchstone, delivering iconic moments that resonate even with those who haven't seen the film. Decades later, the line "Snap out of it!" remains unforgettable, and Cher's joyful morning-after scene, kicking a can through New York streets, perfectly captures the euphoria of falling in love. While Cher and Nicolas Cage shine, Olympia Dukakis, who won the 1988 Oscar for Best Supporting Actress, steals the show with her portrayal of a woman who understands the bittersweet complexities of enduring love.
10. When Harry Met Sally… (1989)
No romantic comedy list is complete without Rob Reiner's timeless exploration of friendship and love. Written by Nora Ephron and starring Billy Crystal, Meg Ryan, and Carrie Fisher, this film has become the gold standard for rom-coms. Its blend of witty dialogue, philosophical musings on relationships, and a heartfelt climax has influenced nearly every romantic comedy made in the past 35 years.
11. Defending Your Life (1991)
Albert Brooks masterfully blends humor and romance in this imaginative tale set in the afterlife. While his signature critique of consumer culture is present, Defending Your Life ultimately shines as a celebration of love's ability to conquer fear. By the film's end, cynicism gives way to pure joy, underscored by Meryl Streep's captivating performance as Brooks's love interest.
12. Boomerang (1992)
Eddie Murphy's venture into romantic comedy, despite some dated humor, remains one of his standout performances. Directed by Reginald Hudlin, Boomerang features an all-star cast, including Halle Berry and the unforgettable Grace Jones. The film follows Murphy as he meets his match in Robin Givens, a woman who outplays him at his own game. With sharp dialogue, standout performances, and a legendary scene-stealing turn by Eartha Kitt, Boomerang is a timeless rom-com ahead of its era.
13. Four Weddings and a Funeral (1994)
Richard Curtis, known for rom-com gems like Notting Hill and Love Actually, crafted one of his finest works with this Mike Newell-directed classic. The film follows a group of friends through life's milestones, with Hugh Grant delivering a career-defining performance as the endearingly awkward romantic lead. Its blend of humor, heart, and charm has made it a beloved staple of the genre.
14. Clueless (1995)
For many who grew up in the 1990s, Amy Heckerling's Clueless remains the ultimate rom-com benchmark. A modern take on Jane Austen's Emma, the film feels timeless despite its '90s slang and fashion. Its witty dialogue, iconic costumes, and memorable soundtrack are unforgettable, but what truly endures is its heartfelt story of a young woman (Alicia Silverstone) discovering what she truly desires.
15. You've Got Mail (1998)
Nora Ephron, a luminary of modern romantic comedies, delivers one of her most enduring works with You've Got Mail. Building on themes from Sleepless In Seattle, the film explores connection in a digital age, proving that love can transcend physical barriers. Inspired by the 1937 play Parfumerie and its 1940 adaptation The Shop Around the Corner, the film thrives on the chemistry of Tom Hanks and Meg Ryan, who make their characters' unlikely romance feel destined.
16. But I'm a Cheerleader (1999)
Jamie Babbit's But I'm a Cheerleader stands out as a unique and vibrant cult classic. Natasha Lyonne and Clea DuVall deliver heartfelt performances as two women who find love while enduring a gay conversion therapy camp. Supported by standout roles from Cathy Moriarty, Melanie Lynskey, and RuPaul, the film contrasts its bright, hyper-stylized world with the emotional depth of its characters, celebrating self-discovery and love on one's own terms.
17. The 40-Year-Old Virgin (2005)
The 2000s introduced a wave of raunchy comedies about immature men, but Judd Apatow's directorial debut stands out as a romantic comedy gem. What could have been a one-note joke transforms into a heartfelt story, thanks to Apatow's direction and a stellar cast led by Steve Carell. His character overcomes romantic insecurities not through gimmicks but through genuine warmth and kindness. Catherine Keener's casting as the love interest elevates the film to classic status.
18. It's Complicated (2009)
As Nora Ephron's influence waned, Nancy Meyers became the torchbearer for sophisticated, emotionally rich romantic comedies. While Something's Gotta Give and The Holiday are beloved, It's Complicated stands as Meyers's most refined work. The film explores the complexities of middle-aged love, with Meryl Streep delivering a stellar performance alongside Steve Martin, Alec Baldwin, John Krasinski, and Zoe Kazan, all of whom bring warmth and depth to the story.
19. The Big Sick (2017)
Inspired by the real-life romance of Kumail Nanjiani and Emily V. Gordon, The Big Sick explores how love endures even when life—and the specter of death—intervenes. Directed by Michael Showalter, known for Wet Hot American Summer, the film balances absurd humor with heartfelt emotion, highlighting the strangeness of the journey while delivering a deeply moving payoff.
20. Palm Springs (2020)
A standout romantic comedy for 2020, Palm Springs brilliantly captures the challenge of finding connection in a monotonous world. Andy Samberg and Cristin Milioti shine as a couple navigating a time loop, using the premise as both a metaphor for long-term relationships and a clever narrative device. Their chemistry and the film's inventive storytelling ensure its place as a modern rom-com classic.
