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The Best '50s Romantic Comedies

Updated June 14, 2019 1.6k votes 285 voters 13.8k views38 items

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.
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  • 1
    Roman Holiday is listed (or ranked) 1 on the list The Best '50s Romantic Comedies
    94
    16

    Roman Holiday

    Audrey Hepburn, Gregory Peck

    Released1953

    Directed byWilliam Wyler

    Roman Holiday is a 1953 American romantic comedy directed and produced by William Wyler. It... more on Wikipedia

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  • 2
    Sabrina is listed (or ranked) 2 on the list The Best '50s Romantic Comedies
    93
    20

    Sabrina

    Audrey Hepburn, Humphrey Bogart

    Released1954

    Directed byBilly Wilder

    Sabrina is a 1954 American romantic comedy film directed by Billy Wilder, adapted for the... more on Wikipedia
  • 3
    Singin' in the Rain is listed (or ranked) 3 on the list The Best '50s Romantic Comedies
    80
    15

    Singin' in the Rain

    Debbie Reynolds, Gene Kelly

    Released1952

    Directed byStanley Donen, Gene Kelly

    Singin' in the Rain is a 1952 American musical comedy film directed by Gene Kelly and Stanley... more on Wikipedia
  • 4
    Pillow Talk is listed (or ranked) 4 on the list The Best '50s Romantic Comedies
    81
    17

    Pillow Talk

    Doris Day, Rock Hudson

    Released1959

    Directed byMichael Gordon

    Pillow Talk is a 1959 Eastmancolor romantic comedy film in CinemaScope directed by Michael... more on Wikipedia

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  • 5
    Some Like It Hot is listed (or ranked) 5 on the list The Best '50s Romantic Comedies
    63
    12

    Some Like It Hot

    Marilyn Monroe, Jack Lemmon

    Released1959

    Directed byBilly Wilder

    Some Like It Hot is a 1959 American comedy film set in 1929, directed by Billy Wilder,... more on Wikipedia
  • 6
    Lady and the Tramp is listed (or ranked) 6 on the list The Best '50s Romantic Comedies
    60
    24

    Lady and the Tramp

    Peggy Lee, Stan Freberg

    Released1955

    Directed byWilfred Jackson, Hamilton Luske, Clyde Geronimi

    Lady and the Tramp is a 1955 American animated musical romance film directed by Clyde... more on Wikipedia

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  • 7
    Gentlemen Prefer Blondes is listed (or ranked) 7 on the list The Best '50s Romantic Comedies
    50
    16

    Gentlemen Prefer Blondes

    Marilyn Monroe, Jane Russell

    Released1953

    Directed byHoward Hawks

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  • 8
    How to Marry a Millionaire is listed (or ranked) 8 on the list The Best '50s Romantic Comedies
    46
    13

    How to Marry a Millionaire

    Marilyn Monroe, Lauren Bacall

    Released1953

    Directed byJean Negulesco

    How to Marry a Millionaire is a 1953 American romantic comedy film directed by Jean Negulesco... more on Wikipedia
  • 9
    Funny Face is listed (or ranked) 9 on the list The Best '50s Romantic Comedies
    43
    13

    Funny Face

    Audrey Hepburn, Fred Astaire

    Released1957

    Directed byStanley Donen

    Funny Face is a 1957 American musical romantic comedy film directed by Stanley Donen and... more on Wikipedia
  • 10
    The Quiet Man is listed (or ranked) 10 on the list The Best '50s Romantic Comedies
    41
    13

    The Quiet Man

    John Wayne, Maureen O'Hara

    Released1952

    Directed byJohn Ford

    The Quiet Man is a 1952 American romantic comedy-drama film directed by John Ford. It stars... more on Wikipedia

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  • 11
    High Society is listed (or ranked) 11 on the list The Best '50s Romantic Comedies
    37
    13

    High Society

    Frank Sinatra, Grace Kelly

    Released1956

    Directed byCharles Walters

    High Society is a 1956 American musical comedy film directed by Charles Walters and starring... more on Wikipedia
  • 12
    The Seven Year Itch is listed (or ranked) 12 on the list The Best '50s Romantic Comedies
    41
    19

    The Seven Year Itch

    Marilyn Monroe, Carolyn Jones

    Released1955

    Directed byBilly Wilder

    The Seven Year Itch is a 1955 American romantic comedy film based on a three-act play with the... more on Wikipedia

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  • 13
    Gigi is listed (or ranked) 13 on the list The Best '50s Romantic Comedies
    34
    18

    Gigi

    Eva Gabor, Leslie Caron

    Released1958

    Directed byVincente Minnelli

    Gigi is a 1958 American Metrocolor musical romantic comedy film directed by Vincente Minnelli.... more on Wikipedia

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  • 14
    Gidget is listed (or ranked) 14 on the list The Best '50s Romantic Comedies
    31
    14

    Gidget

    Yvonne Craig, Sandra Dee

    Released1959

    Directed byPaul Wendkos

    Gidget is a 1959 Columbia Pictures CinemaScope feature film. It stars Sandra Dee, Cliff... more on Wikipedia
  • 15
    Father of the Bride is listed (or ranked) 15 on the list The Best '50s Romantic Comedies
    28
    14

    Father of the Bride

    Elizabeth Taylor, Spencer Tracy

    Released1950

    Directed byVincente Minnelli

    Father of the Bride is a 1950 American comedy film about a man trying to cope with... more on Wikipedia

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  • 16
    Houseboat is listed (or ranked) 16 on the list The Best '50s Romantic Comedies
    28
    17

    Houseboat

    Sophia Loren, Cary Grant

    Released1958

    Directed byMelville Shavelson

    Houseboat is a 1958 romantic comedy film starring Cary Grant, Sophia Loren, Martha Hyer, Paul... more on Wikipedia
  • 17
    The Tender Trap is listed (or ranked) 17 on the list The Best '50s Romantic Comedies
    22
    17

    The Tender Trap

    Frank Sinatra, Debbie Reynolds

    Released1955

    Directed byCharles Walters

    The Tender Trap is a CinemaScope comedy starring Frank Sinatra, Debbie Reynolds, David Wayne,... more on Wikipedia
  • 18
    Love in the Afternoon is listed (or ranked) 18 on the list The Best '50s Romantic Comedies
    24
    23

    Love in the Afternoon

    Audrey Hepburn, Gary Cooper

    Released1957

    Directed byBilly Wilder

    Love in the Afternoon is a 1957 American romantic comedy film produced and directed by Billy... more on Wikipedia

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  • 19
    Teacher's Pet is listed (or ranked) 19 on the list The Best '50s Romantic Comedies
    19
    16

    Teacher's Pet

    Jackie Cooper, Norman Chaney

    Released1930

    Directed byRobert F. McGowan

    Teacher's Pet is a 1930 two-reel comedy short; part of the Our Gang series. It was produced by... more on Wikipedia
  • 20
    Daddy Long Legs is listed (or ranked) 20 on the list The Best '50s Romantic Comedies
    19
    17

    Daddy Long Legs

    Fred Astaire, Leslie Caron

    Released1955

    Directed byJean Negulesco

    Daddy Long Legs is a Hollywood musical comedy film set in France, New York City, and the... more on Wikipedia

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  • 21
    Kiss Me Kate is listed (or ranked) 21 on the list The Best '50s Romantic Comedies
    15
    14

    Kiss Me Kate

    Ann Miller, Keenan Wynn

    Released1953

    Directed byGeorge Sidney

    Kiss Me Kate is the 1953 MGM film adaptation of the Broadway musical of the same... more on Wikipedia
  • 22
    The Farmer Takes a Wife is listed (or ranked) 22 on the list The Best '50s Romantic Comedies
    12
    11

    The Farmer Takes a Wife

    Julie Newmar, Betty Grable

    Released1953

    Directed byVictor Fleming, Henry Levin

    The Farmer Takes a Wife is a 1953 romantic musical comedy film directed by Henry Levin.
  • 23
    Our Girl Friday is listed (or ranked) 23 on the list The Best '50s Romantic Comedies
    12
    13

    Our Girl Friday

    Peter Sellers, Joan Collins

    Released1953

    Directed byNoel Langley

    Our Girl Friday is a 1953 British comedy film starring Joan Collins, George Cole, Kenneth More... more on Wikipedia
  • 24
    The Big Hangover is listed (or ranked) 24 on the list The Best '50s Romantic Comedies
    10
    11

    The Big Hangover

    Elizabeth Taylor, Van Johnson

    Released1950

    Directed byNorman Krasna

    The Big Hangover is a 1950 film directed by Norman Krasna.
  • 25
    Ain't Misbehavin' is listed (or ranked) 25 on the list The Best '50s Romantic Comedies
    7
    9

    Ain't Misbehavin'

    Piper Laurie, Mamie Van Doren

    Released1955

    Directed byEdward Buzzell

    Ain't Misbehavin '​ is a 1955 musical film released by Universal-International and starring... more on Wikipedia
FilmsFilmEntertainmentComedy1950sClassic MoviesRomantic MoviesRomance50s MoviesRomantic Comediestop 25