Sponsored
303 voters

The Best '50s Romantic Comedies

Updated June 14, 2019 1.7k votes 303 voters 14.7k 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.
Photo:
...more
  • Roman Holiday1
    103
    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

    More Roman Holiday 

    #134 of 782 The Greatest Chick Flicks Ever Made#627 of 1,540 The Most Rewatchable Movies

  • Sabrina2
    96
    21

    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

    More Sabrina 

    #58 of 224 The Best Black and White Movies Ever Made#25 of 75 The Greatest Classic Romance Movies

  • Singin' in the Rain3
    88
    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

    More Singin' in the Rain 

    Every Song in Singin' in the Rain, Ranked by Singability#60 of 246 The Best Rainy Day Movies

  • Pillow Talk4
    86
    18

    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

    More Pillow Talk 

    #343 of 541 The Greatest Guilty Pleasure Movies#51 of 264 Movies That Should Be Made Into Broadway Musicals

  • Some Like It Hot5
    68
    13

    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

    More Some Like It Hot 

    #17 of 675 The Best Movies Roger Ebert Gave Four Stars#284 of 557 The Greatest Film Scores of All Time

  • Lady and the Tramp6
    67
    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

    More Lady and the Tramp 

    #36 of 575 The Best Animated Films Ever#18 of 297 The Best Duos of All Time

  • How to Marry a Millionaire7
    50
    12

    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
  • Gentlemen Prefer Blondes8
    53
    16

    Gentlemen Prefer Blondes

    Marilyn Monroe, Jane Russell

    Released1953

    Directed byHoward Hawks

    Gentlemen Prefer Blondes is a 1953 American musical comedy film based on the 1949 stage...  more

    More Gentlemen Prefer Blondes 

    #154 of 206 Musical Movies With the Best Songs#33 of 51 The Best Musical Love Story Movies

  • Funny Face9
    47
    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
  • High Society10
    42
    12

    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
  • The Quiet Man11
    43
    14

    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

    More The Quiet Man 

    #25 of 50 The Best Movies Based on Short Stories#128 of 152 Movies That Should Never Be Remade

  • The Seven Year Itch12
    42
    20

    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

    More The Seven Year Itch 

    #321 of 1,137 The Absolute Funniest Movies Of All Time#43 of 52 The Best Movies About Having A Midlife Crisis

  • Gigi13
    37
    19

    Gigi

    Eva Gabor, Leslie Caron

    Released1958

    Directed byVincente Minnelli

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

    More Gigi 

    #6 of 1,189 Every Oscar Winning Film Ever#83 of 92 The Very Best Oscar-Winning Movies For Best Picture

  • Gidget14
    33
    15

    Gidget

    Yvonne Craig, Sandra Dee

    Released1959

    Directed byPaul Wendkos

    Gidget is a 1959 Columbia Pictures CinemaScope feature film. It stars Sandra Dee, Cliff...  more
  • Father of the Bride15
    29
    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

    More Father of the Bride 

    #128 of 369 The Best Movies Based On Books#183 of 922 The All-Time Greatest Comedy Films

  • The Tender Trap16
    27
    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
  • Houseboat17
    29
    19

    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
  • Teacher's Pet18
    20
    15

    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
  • Ain't Misbehavin'19
    16
    10

    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
  • A Hole in the Head20
    17
    13

    A Hole in the Head

    Frank Sinatra, Edward G. Robinson

    Released1959

    Directed byFrank Capra

    A Hole in the Head is a comedy film directed by Frank Capra, featuring Frank Sinatra, Edward...  more
  • Love in the Afternoon21
    24
    24

    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

    More Love in the Afternoon 

    #16 of 60 The Best Romance Movies of the '50s#51 of 64 The Best Comedy Movies of the 1950s

  • The Admiral Was a Lady22
    13
    8

    The Admiral Was a Lady

    Edmond O'Brien, Rudy Vallée

    Released1950

    Directed byAlbert S. Rogell

    The Admiral Was a Lady is a 1950 American comedy film directed by Albert S. Rogell. The...  more
  • Kiss Me Kate23
    15
    15

    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
  • Happy Go Lovely24
    11
    9

    Happy Go Lovely

    David Niven, Cesar Romero

    Released1951

    Directed byH. Bruce Humberstone

    Happy Go Lovely is a 1951 British musical comedy film with Technicolor, directed by H. Bruce...  more
  • Daddy Long Legs25
    17
    18

    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