The 1960s were a golden era for romantic comedies. The decade blended old Hollywood charm with emerging modern attitudes toward dating, marriage, and independence. It was a period where glossy studio polish met changing cultural values, creating romcoms that were stylish, witty, and surprisingly timeless. From Doris Day classics to sharp New York stories, the 60s delivered some of the genre’s most iconic moments.
Here are the best romantic comedies of the 1960s that still hold up today.
Pillow Talk (1959, wide release 1960)
Doris Day and Rock Hudson helped define the modern romcom template in this story of two feuding New Yorkers who share a party line. The innuendo is clever, the chemistry is effortless, and the film’s success helped shape the romantic comedies that followed throughout the decade.
Where to watch: Available to stream; sold on physical media and digitally.
The Apartment (1960)
Billy Wilder’s bittersweet classic balances romance and melancholy with rare finesse. Jack Lemmon and Shirley MacLaine play two lonely souls trying to find connection in a cold corporate world. It won Best Picture and remains one of the most emotionally layered romcoms ever made.
Where to watch: Available to stream; sold on physical media and digitally.
That Touch of Mink (1962)
Doris Day and Cary Grant headline this polished tale of mismatched expectations. Day plays a woman seeking love and commitment, while Grant’s wealthy bachelor wants something far more casual. The film’s charm comes from their comedic tug of war and Grant’s impeccable timing.
Where to watch: Available to stream; sold on physical media and digitally.
Charade (1963)
Part romance, part thriller, part Audrey Hepburn at her most stylish. Hepburn and Cary Grant spark in this caper about a widow on the run and the mysterious man trying to protect her. It is equal parts flirtation and suspense, wrapped in Parisian glamour.
Where to watch: Available to stream; sold on physical media and digitally.
Barefoot in the Park (1967)
Based on Neil Simon’s hit play, this story of newlyweds adjusting to their tiny New York apartment is filled with warm humor and gentle conflict. Robert Redford and Jane Fonda bring the script to life with perfect comedic rhythm.
Where to watch: Available to stream; sold on physical media and digitally.
How to Steal a Million (1966)
Audrey Hepburn and Peter O’Toole star in this lighthearted heist romance about a daughter trying to protect her father’s reputation. Their chemistry and the film’s breezy tone make it one of the decade’s most charming escapist romcoms.
Where to watch: Available to stream; sold on physical media and digitally.
Send Me No Flowers (1964)
The final Doris Day and Rock Hudson pairing sees Hudson incorrectly convinced he is dying. The misunderstanding spirals into matchmaking chaos as he tries to secure a future husband for Day’s character. Light, silly, and full of the duo’s signature charm.
Where to watch: Available to stream; sold on physical media and digitally.
Breakfast at Tiffany’s (1961)
Audrey Hepburn’s most iconic role is part comedy, part romance, and part character study. While some elements have aged unevenly, the central chemistry between Hepburn and George Peppard and the film’s stylish New York setting remain irresistible.
Where to watch: Available to stream; sold on physical media and digitally.
Come September (1961)
Rock Hudson, Gina Lollobrigida, Sandra Dee, and Bobby Darin headline this ensemble romcom set at an Italian villa. It is colorful, sunny, and delightfully carefree, capturing the spirit of early 60s travel comedies.
Where to watch: Available to stream; sold on physical media and digitally.
The Thrill of It All (1963)
Another Doris Day favorite, this one centers on a housewife who accidentally becomes a successful TV spokesperson. Her rising fame upends her marriage to a doctor played by James Garner. It is a funny, charming look at celebrity culture long before the influencer era.
Where to watch: Available to stream; sold on physical media and digitally.
Why 1960s RomComs Still Matter
The 60s marked a transition from old-fashioned courtship stories to modern romance. Characters were more independent, relationships were more complicated, and comedy often came from generational shifts rather than simple misunderstandings. These films shaped the romcoms that followed and helped establish many of the genre’s most enduring tropes.
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