The 1950s are often remembered as a time marked by wholesome family values. But that doesn't mean that the decade's moviegoers were opposed to a good love story. Quite the opposite, in fact – the '50s boast some of the most iconic romantic comedies of all time. Some of these heartwarming comedies prove the age-old adage that opposites attract while other top 1950s romantic comedies feature complicated love triangles. All of them starred actors and actresses that were household names then, and whose legacy continues today.
What film should be named the greatest on this list of the best '50s romantic comedies? The animated classic Lady and the Tramp may feature canine lead characters, but the laughter and love at the heart of the film are universal. The legendary actress Peggy Lee provided many of the voices in this Disney masterpiece. Audrey Hepburn's films Funny Face, Sabrina, and Roman Holiday helped solidify her as one of the great romantic leading ladies of the 1950s. Marilyn Monroe was another incredibly popular romantic comedy star in the 1950s. Her movies Gentlemen Prefer Blondes and The Seven Year Itch showcased the seductive beauty and charisma that made her an icon.
It's up to you to decide the best romantic comedy from the 1950s. Grab some popcorn, vote your favorite films up the list, and add any that are missing.1
10316Roman Holiday
Audrey Hepburn, Gregory PeckReleased: 1953
Directed by: William Wyler
Roman Holiday is a 1953 American romantic comedy directed and produced by William Wyler. It... more2
9621Sabrina
Audrey Hepburn, Humphrey BogartReleased: 1954
Directed by: Billy Wilder
Sabrina is a 1954 American romantic comedy film directed by Billy Wilder, adapted for the... more3
8815Singin' in the Rain
Debbie Reynolds, Gene KellyReleased: 1952
Directed by: Stanley Donen, Gene Kelly
Singin' in the Rain is a 1952 American musical comedy film directed by Gene Kelly and Stanley... more4
8618Pillow Talk
Doris Day, Rock HudsonReleased: 1959
Directed by: Michael Gordon
Pillow Talk is a 1959 Eastmancolor romantic comedy film in CinemaScope directed by Michael... more5
6813Some Like It Hot
Marilyn Monroe, Jack LemmonReleased: 1959
Directed by: Billy Wilder
Some Like It Hot is a 1959 American comedy film set in 1929, directed by Billy Wilder,... more6
6724Lady and the Tramp
Peggy Lee, Stan FrebergReleased: 1955
Directed by: Wilfred Jackson, Hamilton Luske, Clyde Geronimi
Lady and the Tramp is a 1955 American animated musical romance film directed by Clyde... more7
5012How to Marry a Millionaire
Marilyn Monroe, Lauren BacallReleased: 1953
Directed by: Jean Negulesco
How to Marry a Millionaire is a 1953 American romantic comedy film directed by Jean Negulesco... more8
5316Gentlemen Prefer Blondes
Marilyn Monroe, Jane RussellReleased: 1953
Directed by: Howard Hawks
Gentlemen Prefer Blondes is a 1953 American musical comedy film based on the 1949 stage... more9
4713Funny Face
Audrey Hepburn, Fred AstaireReleased: 1957
Directed by: Stanley Donen
Funny Face is a 1957 American musical romantic comedy film directed by Stanley Donen and... more10
4212High Society
Frank Sinatra, Grace KellyReleased: 1956
Directed by: Charles Walters
High Society is a 1956 American musical comedy film directed by Charles Walters and starring... more11
4314The Quiet Man
John Wayne, Maureen O'HaraReleased: 1952
Directed by: John Ford
The Quiet Man is a 1952 American romantic comedy-drama film directed by John Ford. It stars... more12
4220The Seven Year Itch
Marilyn Monroe, Carolyn JonesReleased: 1955
Directed by: Billy Wilder
The Seven Year Itch is a 1955 American romantic comedy film based on a three-act play with the... more13
3719Gigi
Eva Gabor, Leslie CaronReleased: 1958
Directed by: Vincente Minnelli
Gigi is a 1958 American Metrocolor musical romantic comedy film directed by Vincente Minnelli.... more14
3315Gidget
Yvonne Craig, Sandra DeeReleased: 1959
Directed by: Paul Wendkos
Gidget is a 1959 Columbia Pictures CinemaScope feature film. It stars Sandra Dee, Cliff... more15
2914Father of the Bride
Elizabeth Taylor, Spencer TracyReleased: 1950
Directed by: Vincente Minnelli
Father of the Bride is a 1950 American comedy film about a man trying to cope with... more16
2717The Tender Trap
Frank Sinatra, Debbie ReynoldsReleased: 1955
Directed by: Charles Walters
The Tender Trap is a CinemaScope comedy starring Frank Sinatra, Debbie Reynolds, David Wayne,... more17
2919Houseboat
Sophia Loren, Cary GrantReleased: 1958
Directed by: Melville Shavelson
Houseboat is a 1958 romantic comedy film starring Cary Grant, Sophia Loren, Martha Hyer, Paul... more18
2015Teacher's Pet
Jackie Cooper, Norman ChaneyReleased: 1930
Directed by: Robert F. McGowan
Teacher's Pet is a 1930 two-reel comedy short; part of the Our Gang series. It was produced by... more19
1610Ain't Misbehavin'
Piper Laurie, Mamie Van DorenReleased: 1955
Directed by: Edward Buzzell
Ain't Misbehavin ' is a 1955 musical film released by Universal-International and starring... more20
1713A Hole in the Head
Frank Sinatra, Edward G. RobinsonReleased: 1959
Directed by: Frank Capra
A Hole in the Head is a comedy film directed by Frank Capra, featuring Frank Sinatra, Edward... more21
2424Love in the Afternoon
Audrey Hepburn, Gary CooperReleased: 1957
Directed by: Billy Wilder
Love in the Afternoon is a 1957 American romantic comedy film produced and directed by Billy... more22
138The Admiral Was a Lady
Edmond O'Brien, Rudy ValléeReleased: 1950
Directed by: Albert S. Rogell
The Admiral Was a Lady is a 1950 American comedy film directed by Albert S. Rogell. The... more23
1515Kiss Me Kate
Ann Miller, Keenan WynnReleased: 1953
Directed by: George Sidney
Kiss Me Kate is the 1953 MGM film adaptation of the Broadway musical of the same... more24
119Happy Go Lovely
David Niven, Cesar RomeroReleased: 1951
Directed by: H. Bruce Humberstone
Happy Go Lovely is a 1951 British musical comedy film with Technicolor, directed by H. Bruce... more25
1718Daddy Long Legs
Fred Astaire, Leslie CaronReleased: 1955
Directed by: Jean Negulesco
Daddy Long Legs is a Hollywood musical comedy film set in France, New York City, and the... more
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