Best Romantic Comedies

WTOP Film Critic Jason Fraley ranks the best romantic comedies of all time in the gallery below.

Not seeing your favorite movie? It’s probably in a different genre! Check out the full list here.

30. ‘500 Days of Summer’ (2009) – Marc Web

Zooey Deschanel has Joseph Gordon-Levitt snapping to “You Make My Dreams Come True” before his heartbreaking split screen of expectations vs. reality.

29. ‘What’s Up, Doc?’ (1972) – Peter Bogdanovich

Barbra Streisand and Ryan O’Neal delivered one of the ’70s top-grossing films with this screwball rom-com about four identical plaid bags, as O’Neal mocked his “Love Story” quote as “the dumbest thing I’ve ever heard.”

28. ‘Hitch’ (2005) – Andy Tennant

Will Smith plays a charming “date doctor” trying to set up a hopelessly dorky Kevin James, only to find it much harder to woo Eva Mendes’ jaded gossip columnist in the hectic dating culture of New York City.

27. ‘Pillow Talk’ (1959) – Michael Gordon

The best of the Rock Hudson-Doris Day pictures features an Oscar-winning script about a man and a woman who share a party line, and though they cannot stand each other in person, he has fun romancing her with his voice disguised.

26. ‘My Man Godfrey’ (1936) – Gregory La Cava

Carole Lombard plays a scatterbrained socialite who hires a poor “forgotten man” named Godfrey (William Powell) to become her wealthy family’s butler.

25. ‘Mr. Deeds Goes to Town’ (1934) – Frank Capra

Gary Cooper is sympathetic as a local yokel who inherits a fortune and falls head over heels for Jean Arthur, who is selling his gossip to the tabloids.

24. ‘Love Actually’ (2003) – Richard Curtis

After “Four Weddings and a Funeral,” Richard Curtis delivered this mosaic about eight London couples at Christmas, including Liam Neeson, Emma Thompson, Bill Nighy, Colin Firth, Hugh Grant and Kiera Knightley.

23. ‘The Palm Beach Story’ (1942) – Preston Sturges

Joel McCrea reunites with Preston Sturges after “Sullivan’s Travels” to play an inventor seeking funding for his next big idea, causing his resourceful wife Claudette Colbert to divorce him and marry a millionaire so she can send him the cash.

22. ‘Manhattan’ (1979) – Woody Allen

Black-and-white cinematography beautifully captured New York City fireworks set to the Gerswhins’ “Rhapsody in Blue,” but the subplot with Oscar-nominated Mariel Hemingway is now cringeworthy in hindsight.

21. ‘The Awful Truth’ (1937) – Leo McCarey

Cary Grant and Irene Dunne play a married couple who begin divorce proceedings, then start undermining each other’s attempts to find new lovers in this groundbreaking romantic comedy that won Leo McCarey an Oscar for Best Director.

20. ‘Something’s Gotta Give’ (2003) – Nancy Meyers

After Nora Ephron shattered the glass ceiling, Nancy Meyers dominated the genre with Jack Nicholson learning to stop chasing younger women and finding a woman closer to his own age, winning Diane Keaton a Golden Globe.

19. ‘Ninotchka’ (1939) – Ernst Lubitsch

“Garbo laughs!” That’s how MGM promoted Greta Garbo’s first comedic turn, playing a stern Russian sent to Paris on official business, only to fall for a capitalist who represents everything she is supposed to detest in this gem by Ernst Lubitsch.

18. ‘As Good as It Gets’ (1997) – James L. Brooks

Helen Hunt plays a single-mother waitress and Jack Nicholson plays a cranky author, who overcomes his O.C.D. impulses and bigoted tendencies to declare, “You make me want to be a better man.” Both won Oscars for their roles.

17. ‘The Lady Eve’ (1941) – Preston Sturges

Few filmmakers can rival the meteoric run of Preston Sturges from 1940-1944, including this high-concept gem starring Barbara Stanwyck as a con artist who falls for millionaire Henry Fonda, splits with him, then disguises herself to come back and taunt him.

16. ‘Pretty Woman’ (1990) – Garry Marshall

Despite the dated theme of a Pygmalion makeover for a “prostitute with a heart of gold,” there’s no denying the charm of Julia Roberts in her Golden Globe-winning role, erupting in a contagious laugh as Richard Gere closed a jewelry box on her hand.

15. ‘Trouble in Paradise’ (1932) – Ernst Lubitsch

The “Lubitsch Touch” was on full display in this masterpiece about a gentleman thief and lady pickpocket who unite to con a perfume company owner. The film benefited from pre-Code antics that would have been censored if released a few years later.

14. ‘There’s Something About Mary’ (1998) – Farrelly Brothers

“Is that hair gel?” Cameron Diaz and Ben Stiller had us in stitches with a jammed zipper emergency: “We’ve got a bleeder!”

13. ‘Harold & Maude’ (1971) – Hal Ashby

In “There’s Something About Mary,” Cameron Diaz title character calls “Harold & Maude” the greatest love story of our time. That’s hyperbole, but Hal Ashby memorably directs to an ageless Cat Stevens soundtrack.

12. ‘Say Anything’ (1989) – Cameron Crowe

Few movie images are more iconic than John Cusack’s Lloyd Dobbler outside his lover’s bedroom window, hoisting a boom box to blare Peter Gabriel’s “In Your Eyes” in this irresistible rom-com by Cameron Crowe.

11. ‘Sleepless in Seattle’ (1993) – Nora Ephron

Nora Ephron’s directorial debut cast Tom Hanks as a Seattle widower whose son calls a radio talk show to find his father a partner, catching the ear of Baltimore journalist Meg Ryan, who agrees to meet him atop the Empire State Building.

10. ‘The Shop Around the Corner’ (1940) – Ernst Lubitsch

The original “You’ve Got Mail” came well before email correspondence, as Jimmy Stewart and Margaret Sullavan left hand-written notes in post-office boxes, not knowing that these anonymous pen pals are actually co-workers who despise each other.

9. ‘Roman Holiday’ (1953) – William Wyler

Audrey Hepburn went from unknown to Oscar winner as a restless Princess Ann who goes undercover as a peasant to romp around Rome with Gregory Peck in this reverse-Pygmalion tale that plays like the opposite of her role in “My Fair Lady.”

8. ‘Bringing Up Baby’ (1938) – Howard Hawks

Cary Grant and Katharine Hepburn were absolutely adorable as a hapless paleontologist and a scatterbrained heiress who fall in love while searching for their pet leopard Baby in Howard Hawks’ screwball comedy of phallic bone symbolism.

7. ‘Jerry Maguire’ (1996) – Cameron Crowe

Equal parts weepy romance (“You had me at hello”) and hilarious comedy (“Show me the money!”), Crowe crafted an instant rom-com classic as Renee Zellweger falls for fired colleague Tom Cruise, a sports agent for Oscar-winning football star Cuba Gooding Jr.

6. ‘The Apartment’ (1960) – Billy Wilder

Cameron Crowe’s favorite movie is Billy Wilder’s rom-com “The Apartment,” a Best Picture winner about a hypochondriac (Jack Lemmon) who climbs the company ladder by loaning his apartment to his boss to have trysts with his mistress (Shirley MacLaine).

5. ‘The Philadelphia Story’ (1940) – George Cukor

Labeled box-office poison after her misunderstood work in “Bringing Up Baby” (1938), Katharine Hepburn rebounded with her career best, forming the most star-studded love triangle in history between Cary Grant and Jimmy Stewart (“Oh, C.K. Dexter Haven!”).

4. ‘His Girl Friday’ (1940) – Howard Hawks

Howard Hawks crafted arguably the greatest screwball comedy of all time as Cary Grant’s newspaper editor tried every trick in the book to keep his ace reporter and ex-wife Rosalind Russell from re-marrying, marking a proto-feminist gender shift after “The Front Page.”

3. ‘It Happened One Night’ (1934) – Frank Capra

Two (hitchhiker) thumbs up for Capra’s pioneering rom-com, as Clark Gable and Claudette Colbert made the “Walls of Jericho” come tumbling down in one of only three films to win the “Big Five” Oscars: Best Picture, Director, Actor, Actress and Screenplay.

2. ‘Annie Hall’ (1977) – Woody Allen

The world fell for Diane Keaton’s wardrobe in this inventive Best Picture, using direct address, split-screens, out-of-body experiences, subtitles of character thoughts, animated visions and even famous figures stepping in from off screen to correct the record.

1. ‘When Harry Met Sally’ (1989) – Rob Reiner

Billy Crystal and Meg Ryan were never better than as the title lovers who evolve from hating to loving each other in this perfect rom-com by writer Nora Ephron and director Rob Reiner, whose mother delivers the orgasmic line: “I’ll have what she’s having.”

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Jason Fraley

Hailed by The Washington Post for “his savantlike ability to name every Best Picture winner in history," Jason Fraley began at WTOP as Morning Drive Writer in 2008, film critic in 2011 and Entertainment Editor in 2014, providing daily arts coverage on-air and online.

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