I thought it would be fun to share some information about some of the most compelling films featuring actresses in gender-defying roles as well as actresses who just looked darn good in menswear but the list of names I compiled exceeded my expectations. What follows isn’t a complete list of films featuring cross-dressing actresses but I hope it’s a good jumping off point for anyone curious about the history of girls being boys in the movies.

Top: Mary Pyckford in POOR LITTLE PEPPINA (1916) and Clara Bow in DOWN TO THE SEA IN SHIPS (1923)
Bottom: Gloria Swanson in THE HUMMING BIRD (1924) and Marion Davies in BEVERLY OF GRAUSTARK(1929)

One of the earliest examples of a woman cross-dressing in the movies can be traced to Mary Pickford. Pickford was known as “America’s Sweetheart” and she was one of the most beloved actresses of the silent era. In 1916 she appeared in Sidney Olcott’s POOR LITTLE PEPPINA where she played a young woman named Peppina who was kidnapped by mobsters in New York and taken to Italy. Once she reaches a reasonable age Peppina is expected to marry a man she has no feelings for so she decides to run away. After disguising herself as a boy, Peppina boards a ship and heads to New York where she finds work as a “messenger boy.” The films end with Peppina reuniting with her wealthy parents and returning to her previous life as a girl. After Mary Pickford formed United Artists with D.W. Griffith, Charlie Chaplin and Douglas Fairbanks in 1919, she went on to play another gender-defying role as LITTLE LORD FAUNTLEROY in a 1921 adaptation of Frances Hodgson Burnett’s children’s novel.

Other early noteworthy examples include Clara Bow who portrayed a love-struck girl that disguises herself as a boy in order to board a whaling ship in DOWN TO THE SEA IN SHIPS (1923). In THE HUMMINGBIRD(1924), Gloria Swanson plays a petty thief who dresses as a boy and follows her lover into war after he enlists. And actress Marion Davies portrayed male characters in many of her films including LITTLE OLD NEW YORK (1923), THE CARDBOARD LOVER (1928) and BEVERLY OF GRAUSTARK (1929). Rumors suggest that her paramour, William Randolph Hearst, encouraged Marion to take “butch” parts because he enjoyed seeing her dressed in male clothing. I don’t know if these rumors hold any weight but Davies did cross-dress in many of the movies she appeared in.

Top: Louise Brooks in BEGGARS OF LIFE (1928) and Dorothy Coonan Wellman in WILD BOYS OF THE ROAD (1933) 
Bottom: Katharine Hepburn in SYLVIA SCARLETT (1935) and Veronica Lake in SULLIVAN’S TRAVELS (1941)

During the Great Depression, many actresses donned male clothing to play women who were down on their luck or in some kind of trouble with the law. They often disguised themselves as bums or hobos and tricked their male companions into believing they were boys. One of the best and earliest examples of this can be found in BEGGARS OF LIFE (1928), which stars Louise Brooks as a young woman who disguises herself as a young man after murdering her abusive stepfather. She teams up with a hobo in the hopes of evading the police and the two take to the road together.

Some other good films that deal with similar circumstances include WILD BOYS OF THE ROAD (1933) with Dorothy Coonan Wellman playing a young woman named Sally who disguises herself as a boy so she can ride the rails and look for work. In SYLVIA SCARLETT (1935) Katharine Hepburn decides to dress as a boy after she’s forced to flee France with her father who’s accused of embezzling money. The two end up in England where Hepburn continues her charade until romance blossoms between her and costar Cary Grant. In SULLIVAN’S TRAVELS (1941), Veronica Lake briefly wears men’s clothing in an effort to look less ladylike when she’s on the road with costar, Joel McCrea.

Of course depression era dramas weren’t the only types of films that gave women the chance to sport menswear. Musical numbers often presented actresses with the opportunity to dress up as different characters. Marlene Dietrich mesmerized audiences when she wore a black top hat and a man’s suit while singing cabaret songs in MOROCCO (1930) and she followed that performance by wearing a similar white suit in BLONDE VENUS (1932). Other cross-dressing Dietrich performances can be found in KNIGHTS WITHOUT ARMOUR (1937) and SEVEN SINNERS (1940) where she sports a flattering Navy uniform.

Top: Renate Müller in VIKTOR AND VICTORIA (1933) and Jessie Matthews in FIRST A GIRL (1935)
Bottom: Johanna von Koczian in VIKTOR AND VICTORIA (1957) and Julie Andrews in VICTOR VICTORIA (1982)

One of the most popular gender-defying roles can be found in VIKTOR AND VICTORIA (aka FIRST A GIRLaka VICTOR VICTORIA), which was originally a German comedy film written and directed by Reinhold Schünzel in 1933 before it was turned into a full-blown musical. VIKTOR AND VICTORIA tells the story of a poor struggling singer named Victoria who disguises herself as a man in order to get work. VIKTOR AND VICTORIA has been remade numerous times and the most widely known adaption is probably Blake Edwards’ 1982 version starring his wife, Julie Andrews. It was nominated for multiple Academy Awards including Best Actress.

Actress and tap dancer Eleanor Powell also seemed to enjoy wearing a suit and hat in musicals like BROADWAY MELODY (1936), ROSALIE (1937) and LADY BE GOOD (1941). And Judy Garland occasionally donned menswear too. I find her particularly charming in EASTER PARADE (1948) where she sings a musical number alongside Fred Astaire dressed as a male hobo with a five o’clock shadow.

Top: Greta Garbo in QUEEN CHRISTINA (1933) and Margret Lockwood in THE WICKED LADY (1945)
Bottom: Ingrid Thulin in THE MAGICIAN (1958) and Catriona MacColl in LADY OSCAR (1979)

Costume dramas and period pieces have also given lots of actors the opportunity to cross-dress. Some noteworthy examples include QUEEN CHRISTINA (1933), which features Greta Garbo as a masculine Queen who attracts male and female attention. In THE WICKED LADY (1945), Margaret Lockwood dons a similar disguise to play a wealthy noblewoman who masquerades as a male highwayman and robs her friends and neighbors for kicks.

Ingmar Bergman’s 1958 film THE MAGICIAN is set in the 1840′s and features an androgynous character called Mr. Aman who’s played beautifully by Ingrid Thulin. And Jacques Demy’s 1979 film LADY OSCAR revolves around a character named Oscar (Catriona MacColl), a cross-dressing young woman who was raised as a boy and now works as a guard for Marie Antoinette. The story was adapted from the popular Japanese manga (comic book) series, The Rose of Versailles and has often been performed on stage by the Takarzuka Review, a genderbending 100-year-old Japanese female theater troupe.

More recently actress Tilda Swinton dressed in masculine historical costumes for Sally Potter’s adaptation of Virginia Woolf’s ORLANDO (1992). The film was nominated for two Oscars but it didn’t win any. And speaking of Oscars, Barbra Streisand’s YENTL (1983) and Kimberly Peirce’s BOYS DON’T CRY (1999) are both Academy Award-winning films featuring female characters who dressed as men. In YENTL Barbra Streisand’s plays a woman who is forced to cross-dress in order to get a religious education and in BOYS DON’T CRY Hilary Swank plays a transgendered teen struggling with gender issues.

Last but not least, there have also been some interesting cross-dressing performances from women in horror films. One of my favorite gender-defying roles can be found in THEATRE OF BLOOD (1973), which features Dame Diana Rigg as the daughter of a frustrated stage actor. Rigg dresses up in numerous disguises that involve lots of fake mustaches and bad wigs while helping her father (Vincent Price) kill the critics that ruined his career. William Castle’s HOMICIDAL (1961) is another horror film that features a fascinating and eerie performance from Jean Arless who plays duel sister and brother roles.

As I mentioned at the beginning of my piece, this is just a small sampling of films featuring cross-dressing women in noteworthy roles. In the future, I’d like to return to the topic because it’s a rich one and there’s still lots of uncharted territory to be explored.

by Kimberly Lindbergs, originally written for Turner Classic Movies and published at TCM.com in 2012