Comedy The Best '50s Romantic Comedies  

Ranker Film
491 votes 153 voters 6.3k 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.
list ordered by

1
30 4
Roman Holiday is listed (or ranked) 1 on the list The Best '50s Romantic Comedies
Audrey Hepburn, Gregory Peck, Eddie Albert 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

2
36 6
Sabrina is listed (or ranked) 2 on the list The Best '50s Romantic Comedies
Audrey Hepburn, Humphrey Bogart, William Holden 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

3
29 6
Pillow Talk is listed (or ranked) 3 on the list The Best '50s Romantic Comedies
Doris Day, Rock Hudson, Tony Randall 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

4
27 5
Singin' in the Rain is listed (or ranked) 4 on the list The Best '50s Romantic Comedies
MarylyleMcCue added Debbie Reynolds, Gene Kelly, Rita Moreno 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

5
21 4
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 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

6
20 6
Gentlemen Prefer Blondes is listed (or ranked) 6 on the list The Best '50s Romantic Comedies
Marilyn Monroe, Jane Russell, Harry Carey Gentlemen Prefer Blondes is a 1953 American film adaptation of the 1949 stage musical, released by 20th Century Fox, directed by Howard Hawks, and starring Marilyn Monroe and Jane Russell, with ...more

7
19 6
Lady and the Tramp is listed (or ranked) 7 on the list The Best '50s Romantic Comedies
Peggy Lee, Stan Freberg, Dallas McKennon Lady and the Tramp is a 1955 American animated romantic musical comedy film produced by Walt Disney and released to theaters on 22 June 1955, by Buena Vista Distribution. The 15th film in the ...more

8
19 6
The Seven Year Itch is listed (or ranked) 8 on the list The Best '50s Romantic Comedies
Marilyn Monroe, Carolyn Jones, Evelyn Keyes 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

9
15 4
How to Marry a Millionaire is listed (or ranked) 9 on the list The Best '50s Romantic Comedies
MarylyleMcCue added Marilyn Monroe, Lauren Bacall, Betty Grable 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

10
11 3
Houseboat is listed (or ranked) 10 on the list The Best '50s Romantic Comedies
MarylyleMcCue added Sophia Loren, Cary Grant, Barbara Steele 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

11
12 4
High Society is listed (or ranked) 11 on the list The Best '50s Romantic Comedies
RobLein added Frank Sinatra, Grace Kelly, Bing Crosby 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

12
13 6
The Quiet Man is listed (or ranked) 12 on the list The Best '50s Romantic Comedies
John Wayne, Maureen O'Hara, Barry Fitzgerald 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

13
13 6
Funny Face is listed (or ranked) 13 on the list The Best '50s Romantic Comedies
Audrey Hepburn, Fred Astaire, Suzy Parker Funny Face is a 1957 American musical film directed by Stanley Donen, containing assorted songs by George and Ira Gershwin. Although having the same title as the 1927 Broadway musical Funny Face ...more

14
8 3
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 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

15
8 4
Our Girl Friday is listed (or ranked) 15 on the list The Best '50s Romantic Comedies
MarylyleMcCue added Peter Sellers, Joan Collins, Kenneth More 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.

16
8 4
Teacher's Pet is listed (or ranked) 16 on the list The Best '50s Romantic Comedies
Jackie Cooper, Norman Chaney, Allen Hoskins 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

17
8 4
Gidget is listed (or ranked) 17 on the list The Best '50s Romantic Comedies
Yvonne Craig, Sandra Dee, Cliff Robertson 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

18
6 2
Kiss Me Kate is listed (or ranked) 18 on the list The Best '50s Romantic Comedies
Ann Miller, Keenan Wynn, Kathryn Grayson 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

19
6 3
Daddy Long Legs is listed (or ranked) 19 on the list The Best '50s Romantic Comedies
MarylyleMcCue added Fred Astaire, Leslie Caron, Thelma Ritter 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

20
7 5
Gigi is listed (or ranked) 20 on the list The Best '50s Romantic Comedies
Eva Gabor, Leslie Caron, Louis Jourdan 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

21
3 2
The Farmer Takes a Wife is listed (or ranked) 21 on the list The Best '50s Romantic Comedies
Julie Newmar, Betty Grable, Thelma Ritter The Farmer Takes a Wife is a 1953 romantic musical comedy film directed by Henry Levin.

22
8 8
Love in the Afternoon is listed (or ranked) 22 on the list The Best '50s Romantic Comedies
Audrey Hepburn, Gary Cooper, Maurice Chevalier 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

23
4 4
The Tender Trap is listed (or ranked) 23 on the list The Best '50s Romantic Comedies
Frank Sinatra, Debbie Reynolds, Celeste Holm 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

24
3 3
A Hole in the Head is listed (or ranked) 24 on the list The Best '50s Romantic Comedies
Frank Sinatra, Edward G. Robinson, Eleanor Parker A Hole in the Head is a comedy film directed by Frank Capra, featuring Frank Sinatra, Edward G. Robinson, Eleanor Parker, Keenan Wynn, Carolyn Jones, Thelma Ritter, Dub Taylor, Ruby Dandridge, ...more

25
3 3
Operation Mad Ball is listed (or ranked) 25 on the list The Best '50s Romantic Comedies
Mickey Rooney, Jack Lemmon, Ernie Kovacs Operation Mad Ball is a 1957 military comedy starring Jack Lemmon, Ernie Kovacs, Kathryn Grant, Arthur O'Connell, and Mickey Rooney, and directed by Richard Quine. The screenplay is by Blake ...more

26
3 3
Happy Go Lovely is listed (or ranked) 26 on the list The Best '50s Romantic Comedies
David Niven, Cesar Romero, Vera-Ellen 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

27
2 2
Smiles of a Summer Night is listed (or ranked) 27 on the list The Best '50s Romantic Comedies
Bibi Andersson, Eva Dahlbeck, Harriet Andersson Smiles of a Summer Night is a 1955 Swedish comedy film directed by Ingmar Bergman. It was the first of Bergman's films to bring the director international success, due to its exposure at the ...more

28
2 2
Kiss Them for Me is listed (or ranked) 28 on the list The Best '50s Romantic Comedies
Cary Grant, Jayne Mansfield, Deborah Kerr Kiss Them for Me is a 1957 comedy film, directed by Stanley Donen, and released by the Twentieth Century-Fox Film Corporation. The film, an adaptation of the 1945 Broadway play of the same name, ...more

29
2 2
Here Comes the Groom is listed (or ranked) 29 on the list The Best '50s Romantic Comedies
Bing Crosby, Jane Wyman, Dorothy Lamour Here Comes the Groom is a 1951 musical romantic comedy film produced and directed by Frank Capra and starring Bing Crosby and Jane Wyman. Based on a story by Robert Riskin and Liam O'Brien, the ...more

30
1 1
The Ambassador's Daughter is listed (or ranked) 30 on the list The Best '50s Romantic Comedies
Olivia de Havilland, Myrna Loy, John Forsythe The Ambassador's Daughter is a 1956 romantic comedy film written and directed by Norman Krasna.

31
1 1
Ain't Misbehavin' is listed (or ranked) 31 on the list The Best '50s Romantic Comedies
Piper Laurie, Mamie Van Doren, Rory Calhoun Ain't Misbehavin '​ is a 1955 musical film released by Universal-International and starring Rory Calhoun, Piper Laurie, Jack Carson and Mamie Van Doren.

32
1 1
Gentlemen Marry Brunettes is listed (or ranked) 32 on the list The Best '50s Romantic Comedies
Jane Russell, Jeanne Crain, Alan Young Gentlemen Marry Brunettes is a 1955 romantic musical comedy film produced by Russ-Field productions, starring Jane Russell and Jeanne Crain, and released by United Artists. It was directed by ...more

33
1 1
The Admiral Was a Lady is listed (or ranked) 33 on the list The Best '50s Romantic Comedies
Edmond O'Brien, Rudy Vallée, Hillary Brooke The Admiral Was a Lady is a 1950 American comedy film directed by Albert S. Rogell. The working title of the film was Once Over Lightly that was the title of one of the songs in the film. Edmond ...more

34
1 1
The Matchmaker is listed (or ranked) 34 on the list The Best '50s Romantic Comedies
Shirley MacLaine, Anthony Perkins, Shirley Booth The Matchmaker is a 1958 American comedy film directed by Joseph Anthony. The screenplay by John Michael Hayes is based on the 1955 play of the same name by Thornton Wilder. Costumes by Edith

35
1 2
The Big Hangover is listed (or ranked) 35 on the list The Best '50s Romantic Comedies
Elizabeth Taylor, Van Johnson The Big Hangover is a 1950 film directed by Norman Krasna.

36
1 3
La Ronde is listed (or ranked) 36 on the list The Best '50s Romantic Comedies
Simone Signoret, Anton Walbrook, Simone Simon La Ronde is a 1950 film directed by Max Ophüls and based on Arthur Schnitzler's 1897 play of the same name. The title means "the round-dance". The film was nominated for two ...more

37
1 4
The Yellow Cab Man is listed (or ranked) 37 on the list The Best '50s Romantic Comedies
Red Skelton, Edward Arnold, Gloria DeHaven The Yellow Cab Man is a 1950 comedy film directed by Jack Donohue starring Red Skelton, Gloria DeHaven and Edward Arnold. The inventor of unbreakable glass tries to sell it to a taxicab company, ...more

38
0 3
Ask Any Girl is listed (or ranked) 38 on the list The Best '50s Romantic Comedies
Shirley MacLaine, David Niven, Gig Young Ask Any Girl is a 1959 comedy film directed by Charles Walters.