The full ranking
Screwball banter, will-they-won't-they, and the small triumphs of finding the right person. The films that built and rebuilt the most reliable genre Hollywood has.
The Apartment (1960)
Billy Wilder's Best Picture winner. Jack Lemmon's lonely insurance clerk lets his bosses use his Manhattan apartment for affairs, hoping to climb the ladder, then falls for the elevator girl (Shirley MacLaine) who happens to be the boss's mistress. Sharp, devastating, and bittersweet, it's the rom-com in which the laughs hurt.
It Happened One Night (1934)
Frank Capra's screwball template and the first film to sweep the Big Five Oscars (picture, director, screenplay, actor, actress). A runaway heiress (Claudette Colbert) and a wisecracking reporter (Clark Gable) hitchhike from Florida to New York; the bus, the Wall of Jericho, and the carrot scene set the rules every romantic comedy since has played by.
The Princess Bride (1987)
Rob Reiner's swashbuckling fairy tale, adapted by William Goldman from his own novel. A farm boy (Cary Elwes) rescues his true love (Robin Wright) with help from a giant, a Spaniard, and the most quoted dialogue in 1980s cinema. The frame story with a sick kid and his grandfather (Peter Falk) makes it a love story about storytelling itself.
Roman Holiday (1953)
William Wyler's location-shot Roman idyll won Audrey Hepburn her debut Oscar. A bored European princess slips her handlers in Rome and spends a day with an American reporter (Gregory Peck), neither knowing how the other might exploit them. Vespa rides, the Mouth of Truth, and an ending of grown-up grace.
The Philadelphia Story (1940)
George Cukor's high-society farce, written by Donald Ogden Stewart from the Philip Barry play that resurrected Katharine Hepburn's career. A socialite's wedding plans are upended by her ex-husband (Cary Grant) and a tabloid reporter (James Stewart, who won an Oscar). The rare picture in which the talk is the action.
Annie Hall (1977)
Woody Allen's Best Picture winner reinvented the romantic comedy with split screens, subtitles, talking-to-camera asides, and a willingness to end unhappily. Allen's neurotic comic Alvy Singer and Diane Keaton's Annie meet, click, and slowly fall apart over the late 70s in New York. The film that made the genre safe for adults again.
Harold and Maude (1971)
Hal Ashby's pitch-black New Hollywood cult classic. A morbid teenager (Bud Cort) obsessed with staging fake suicides falls for a life-affirming 79-year-old (Ruth Gordon). The Cat Stevens songs, the Jaguar hearse, and the ending have given the film a fierce cross-generational following for half a century.
His Girl Friday (1940)
Howard Hawks's overlapping-dialogue masterwork. Cary Grant's editor schemes to keep his ace reporter and ex-wife (Rosalind Russell) from leaving the paper, and him, by feeding her one last story. The screwball formula refined into something close to a track meet, and still the gold standard for newsroom comedies.
Groundhog Day (1993)
Harold Ramis directs Bill Murray as a cynical TV weatherman doomed to relive February 2nd in Punxsutawney until he becomes a better man. A high-concept comedy that quietly became philosophy: AFI, theologians, and stand-ups all claim it as a foundational text. Andie MacDowell co-stars as the producer he learns to deserve.
When Harry Met Sally... (1989)
Nora Ephron's screenplay and Rob Reiner's direction created the modern American romantic comedy. Over twelve years and four New York scenes, Billy Crystal and Meg Ryan argue whether men and women can be friends without sex getting in the way. The deli scene, the New Year's Eve speech, and the Harry Connick Jr. soundtrack are now genre furniture.
Ranked across 6 sources: Time Out · 100 Best Romcoms of All Time, Ranked · 0.5x Weight (2026); Slashfilm · 15 Best Romantic Comedies of All Time, Ranked · 0.5x Weight (2024); Rolling Stone · 50 Greatest Romantic Comedies of All Time · 0.5x Weight (2024); Rotten Tomatoes · Tomatometer · Ranked by Critic Score · 0.5x Weight (June 2026); Rotten Tomatoes · Popcornmeter · Ranked by Audience Score · 1.5x Weight (June 2026); IMDb · Ranked by User Rating · 1.5x Weight (June 2026). Full scoring is on the Methodology tab above.
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