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The Best '50s Romantic Comedies 

Ranker Film
Updated June 14, 2019 1.2k votes 272 voters 13.1k views 38 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
Audrey Hepburn, Gregory Peck, Eddie Albert

Released: 1953

Directed by: William Wyler

Roman Holiday is a 1953 American romantic comedy directed and produced by William Wyler. It stars Gregory Peck as a reporter and Audrey Hepburn as a royal princess out to see Rome on her own. ...more

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2
Sabrina is listed (or ranked) 2 on the list The Best '50s Romantic Comedies
Audrey Hepburn, Humphrey Bogart, William Holden

Released: 1954

Directed by: Billy Wilder

Sabrina is a 1954 American romantic comedy film directed by Billy Wilder, adapted for the screen by Wilder, Samuel A. Taylor, and Ernest Lehman from Taylor's play Sabrina Fair. It stars Humphrey ...more

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3
Singin' in the Rain is listed (or ranked) 3 on the list The Best '50s Romantic Comedies
MWM added Debbie Reynolds, Gene Kelly, Rita Moreno

Released: 1952

Directed by: Stanley Donen, Gene Kelly

Singin' in the Rain is a 1952 American musical comedy film directed by Gene Kelly and Stanley Donen, starring Kelly, Donald O'Connor and Debbie Reynolds, and choreographed by Kelly and Donen. It ...more

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4
Pillow Talk is listed (or ranked) 4 on the list The Best '50s Romantic Comedies
Doris Day, Rock Hudson, Tony Randall

Released: 1959

Directed by: Michael Gordon

Pillow Talk is a 1959 Eastmancolor romantic comedy film in CinemaScope directed by Michael Gordon. It features Rock Hudson, Doris Day, Tony Randall, Thelma Ritter and Nick Adams. The film was ...more

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5
Some Like It Hot is listed (or ranked) 5 on the list The Best '50s Romantic Comedies
RobLein added Marilyn Monroe, Jack Lemmon, Tony Curtis

Released: 1959

Directed by: Billy Wilder

Some Like It Hot is a 1959 American comedy film set in 1929, directed by Billy Wilder, starring Marilyn Monroe, Tony Curtis and Jack Lemmon. The film is about two musicians who dress in drag in ...more

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6
Lady and the Tramp is listed (or ranked) 6 on the list The Best '50s Romantic Comedies
Peggy Lee, Stan Freberg, Dallas McKennon

Released: 1955

Directed by: Wilfred Jackson, Hamilton Luske, Clyde Geronimi

Lady and the Tramp is a 1955 American animated musical romance film directed by Clyde Geronimi, Wilfred Jackson, and Hamilton Luske. The romantic tale of a sheltered uptown Cocker Spaniel dog ...more

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7
Gentlemen Prefer Blondes... is listed (or ranked) 7 on the list The Best '50s Romantic Comedies
Marilyn Monroe, Jane Russell, Harry Carey

Released: 1953

Directed by: Howard Hawks

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8
How to Marry a Millionai... is listed (or ranked) 8 on the list The Best '50s Romantic Comedies
MWM added Marilyn Monroe, Lauren Bacall, Betty Grable

Released: 1953

Directed by: Jean Negulesco

How to Marry a Millionaire is a 1953 American romantic comedy film directed by Jean Negulesco and produced and written by Nunnally Johnson. The film stars Betty Grable, Marilyn Monroe, and ...more
9
The Seven Year Itch is listed (or ranked) 9 on the list The Best '50s Romantic Comedies
Marilyn Monroe, Carolyn Jones, Evelyn Keyes

Released: 1955

Directed by: Billy Wilder

The Seven Year Itch is a 1955 American romantic comedy film based on a three-act play with the same name by George Axelrod. The film was co-written and directed by Billy Wilder, and stars ...more

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10
The Quiet Man is listed (or ranked) 10 on the list The Best '50s Romantic Comedies
John Wayne, Maureen O'Hara, Barry Fitzgerald

Released: 1952

Directed by: John Ford

The Quiet Man is a 1952 American romantic comedy-drama film directed by John Ford. It stars John Wayne, Maureen O'Hara, Barry Fitzgerald, Ward Bond and Victor McLaglen. The screenplay by Frank ...more

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11
Funny Face is listed (or ranked) 11 on the list The Best '50s Romantic Comedies
Audrey Hepburn, Fred Astaire, Suzy Parker

Released: 1957

Directed by: Stanley Donen

Funny Face is a 1957 American musical romantic comedy film directed by Stanley Donen and written by Leonard Gershe, containing assorted songs by George and Ira Gershwin. Although having the same ...more

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12
High Society is listed (or ranked) 12 on the list The Best '50s Romantic Comedies
RobLein added Frank Sinatra, Grace Kelly, Bing Crosby

Released: 1956

Directed by: Charles Walters

High Society is a 1956 American musical comedy film directed by Charles Walters and starring Bing Crosby, Grace Kelly, and Frank Sinatra. The film was produced by Sol C. Siegel for ...more
13
Gigi is listed (or ranked) 13 on the list The Best '50s Romantic Comedies
Eva Gabor, Leslie Caron, Louis Jourdan

Released: 1958

Directed by: Vincente Minnelli

Gigi is a 1958 American Metrocolor musical romantic comedy film directed by Vincente Minnelli. The screenplay by Alan Jay Lerner is based on the 1944 novella of the same name by Colette. The ...more

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14
Father of the Bride is listed (or ranked) 14 on the list The Best '50s Romantic Comedies
RobLein added Elizabeth Taylor, Spencer Tracy, Joan Bennett

Released: 1950

Directed by: Vincente Minnelli

Father of the Bride is a 1950 American comedy film about a man trying to cope with preparations for his daughter's upcoming wedding. The movie stars Spencer Tracy in the titular role, Joan ...more

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15
Gidget is listed (or ranked) 15 on the list The Best '50s Romantic Comedies
Yvonne Craig, Sandra Dee, Cliff Robertson

Released: 1959

Directed by: Paul Wendkos

Gidget is a 1959 Columbia Pictures CinemaScope feature film. It stars Sandra Dee, Cliff Robertson, and James Darren in a story about a teenager's initiation into the California surf culture and ...more
16
Houseboat is listed (or ranked) 16 on the list The Best '50s Romantic Comedies
MWM added Sophia Loren, Cary Grant, Barbara Steele

Released: 1958

Directed by: Melville Shavelson

Houseboat is a 1958 romantic comedy film starring Cary Grant, Sophia Loren, Martha Hyer, Paul Petersen, Charles Herbert and Mimi Gibson. The movie was directed by Melville Shavelson, who also ...more
17
Teacher's Pet is listed (or ranked) 17 on the list The Best '50s Romantic Comedies
Jackie Cooper, Norman Chaney, Allen Hoskins

Released: 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 Hal Roach, directed by Robert F. McGowan, and originally released to theatres by ...more
18
Daddy Long Legs is listed (or ranked) 18 on the list The Best '50s Romantic Comedies
MWM added Fred Astaire, Leslie Caron, Thelma Ritter

Released: 1955

Directed by: Jean Negulesco

Daddy Long Legs is a Hollywood musical comedy film set in France, New York City, and the fictional college town of Walston, Massachusetts. The film was directed by Jean Negulesco, and stars Fred ...more

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19
The Tender Trap is listed (or ranked) 19 on the list The Best '50s Romantic Comedies
Frank Sinatra, Debbie Reynolds, Celeste Holm

Released: 1955

Directed by: Charles Walters

The Tender Trap is a CinemaScope comedy starring Frank Sinatra, Debbie Reynolds, David Wayne, and Celeste Holm. Based on the 1954 play The Tender Trap by Max Shulman and Robert Paul Smith, it ...more
20
Kiss Me Kate is listed (or ranked) 20 on the list The Best '50s Romantic Comedies
Ann Miller, Keenan Wynn, Kathryn Grayson

Released: 1953

Directed by: George Sidney

Kiss Me Kate is the 1953 MGM film adaptation of the Broadway musical of the same name. Inspired by The Taming of the Shrew, it tells the tale of musical theater actors, Fred Graham and Lilli ...more

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21
The Farmer Takes a Wife ... is listed (or ranked) 21 on the list The Best '50s Romantic Comedies
Julie Newmar, Betty Grable, Thelma Ritter

Released: 1953

Directed by: Victor Fleming, Henry Levin

The Farmer Takes a Wife is a 1953 romantic musical comedy film directed by Henry Levin.
22
Our Girl Friday is listed (or ranked) 22 on the list The Best '50s Romantic Comedies
MWM added Peter Sellers, Joan Collins, Kenneth More

Released: 1953

Directed by: Noel Langley

Our Girl Friday is a 1953 British comedy film starring Joan Collins, George Cole, Kenneth More and Robertson Hare. A woman is shipwrecked with three men on a deserted island.
23
Happy Go Lovely is listed (or ranked) 23 on the list The Best '50s Romantic Comedies
David Niven, Cesar Romero, Vera-Ellen

Released: 1951

Directed by: H. Bruce Humberstone

Happy Go Lovely is a 1951 British musical comedy film with Technicolor, directed by H. Bruce Humberstone and starring Vera Ellen, David Niven, and Cesar Romero. The film was made and first ...more
24
Love in the Afternoon is listed (or ranked) 24 on the list The Best '50s Romantic Comedies
Audrey Hepburn, Gary Cooper, Maurice Chevalier

Released: 1957

Directed by: Billy Wilder

Love in the Afternoon is a 1957 American romantic comedy film produced and directed by Billy Wilder which stars Audrey Hepburn and Gary Cooper. The screenplay by Wilder and I.A.L. Diamond is ...more
25
Ain't Misbehavin' is listed (or ranked) 25 on the list The Best '50s Romantic Comedies
Piper Laurie, Mamie Van Doren, Rory Calhoun

Released: 1955

Directed by: Edward Buzzell

Ain't Misbehavin '​ is a 1955 musical film released by Universal-International and starring Rory Calhoun, Piper Laurie, Jack Carson and Mamie Van Doren.