Cross Dressing Movies

  • 1914
    A Robust Romeo

    A Robust Romeo

    A Robust Romeo

    01914HD

    A Robust Romeo is a 1914 movie starring Roscoe Arbuckle and Emma Bell Clifton.

    A Robust Romeo
  • 1971
    The General Inspector

    The General Inspector

    The General Inspector

    01971HD

    When the governor hears that a general inspector has come to town, fearing that he'll uncover his corruption, he and his government officials panic....

    The General Inspector
  • 1970
    Bibi

    Bibi

    Bibi

    01970HD

    The film tells the story of two brothers who exchange places so that one of them can escape from prison.

    Bibi
  • 1993
    Coping with Crossdressing: The Couples Video

    Coping with Crossdressing: The Couples Video

    Coping with Crossdressing: The Couples Video

    01993HD

    An extremely sympathetic and interesting look into how some couples came to terms with transness and crossdressing in the late eighties and early...

    Coping with Crossdressing: The Couples Video
  • 1928
    A Famous Male Impersonator

    A Famous Male Impersonator

    A Famous Male Impersonator

    01928HD

    A Famous Male Impersonator
  • 2005
    All Shook Up

    All Shook Up

    All Shook Up

    02005HD

    The music of Elvis comes alive in All Shook Up. Inspired by Shakespeare’s Twelfth Night, All Shook Up follows a small Midwestern town that is...

    All Shook Up
  • 1936
    Tomboy

    Tomboy

    Tomboy

    01936HD

    A young woman must pretend to be a man to visit her grandfather, and gets into some romantic scrapes in the process.

    Tomboy
  • 1928
    Sir or Madame

    Sir or Madame

    Sir or Madame

    01928HD

    A girl posing as a knight's male valet is vamped by his fiancée

    Sir or Madame
  • 1970
    Caught in the Can

    Caught in the Can

    Caught in the Can

    01970HD

    Low budget softcore farce where two men cross-dress to go into a women's prison.

    Caught in the Can
  • 1991
    Which Is Scary

    Which Is Scary

    Which Is Scary

    01991HD

    A set of seven portraits consisting of personal accounts from the lives of gays and lesbians. The narration includes stories about coming out,...

    Which Is Scary
  • 2005
    Asta Nilsson's companion

    Asta Nilsson's companion

    Asta Nilsson's companion

    02005HD

    A very old lady has lost her way in a city and a distinguished gentleman decides to follow her home.

    Asta Nilsson's companion
  • 1914
    Lillian's Dilemma

    Lillian's Dilemma

    Lillian's Dilemma

    01914HD

    Lillian dresses as a man to gain access to a boy's school. (from Performing Queer Female Identity on Screen: A Critical Analysis of Five Recent Films)

    Lillian's Dilemma