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Cross dressing and drag in film and television has followed a long history of cross dressing and drag on English stage, and made its appearance in the early days of the silent films. Charlie Chaplin and Stan Laurel brought the tradition from the English music halls when they came to America with Fred Karno's comedy troupe in 1910. Both Chaplin and Laurel occasionally dressed as women in their films. Even the beefy American actor Wallace Beery appeared in a series of silent films as a Swedish woman. The Three Stooges, especially Curly (Jerry Howard), sometimes appeared in drag in their short films. The tradition has continued for many years, usually played for laughs. Only in recent decades have there been dramatic films which included cross dressing, possibly because of strict censorship of American films until the mid 1960s. One early exception was Alfred Hitchcock's thriller Murder!, where the murderer is a transvestite who wears particularly frilly dresses and petticoats. Cross gender acting, on the other hand, refers to actors or actresses portraying a character of the opposite gender.

In Some Like It Hot (1959), two struggling musicians have to dress as women to escape the ire of gangsters. The film is a remake of a 1935 French movie, Fanfare of Love, from the story by Robert Thoeren and Michael Logan, which was itself remade in 1951 by German director Kurt Hoffmann as Fanfares of Love. In Blake Edwards's 1982 musical comedy film Victor/Victoria, Victoria Grant, a struggling soprano, is unable to find work but she finds success when she becomes "Count Victor Grazinski", a female impersonator. The film is a remake of Viktor und Viktoria, a German film of 1933. David Henry Hwang's 1988 play M. Butterfly focuses on a love affair between a French diplomat and a male Beijing opera singer who plays dan, or female, roles. Dr. Frank 'n' Furter in The Rocky Horror Picture Show wore nothing but women's clothing the entire film/play. In The Drew Carey Show, Drew's brother, Steve Carey, is a cross dresser. Robin Williams played a divorced father who dressed as a nanny to be with his children in the 1993 comedy Mrs. Doubtfire. Dame Edna was an elderly drag queen with "wisteria colored hair" who did international chat shows in the 1990s.

In the documentary Giuliani Time there are excerpts from Rudy Giuliani's appearance in a video, which was shown for the occasion of an Inner Circle press dinner. The 1936 Polish film Bohaterowie Sybiru has an episode where Polish insurgents exiled to Siberia are partying with Siberian peasants. Two Polish officers make a mock performance of a Polish folk dance, with one of them making a makeshift impersonation of a woman. There are quite a few adaptations of the 1892 farce Charley's Aunt. In the original, a teenager impersonates his friend's aunt.

Bugs Bunny frequently cross dresses in his cartoons for either comedic effect, or to confound a male opponent. Notable examples include "Rabbit of Seville", "What's Opera Doc" and "Rabbit Seasoning", all in attempts to deceive Elmer Fudd. Doctor N. Gin from the Crash Bandicoot series wears a ballerina dancer outfit in Crash Tag Team Racing. The tutu, obtained through one of Crash's missions, is an alternative costume that made N. Gin feel "pretty" and boosted his self esteem. Him from The Powerpuff Girls series is shown every time, wearing a typical skirt, fishnet stockings, and high heeled boots. Jessie and James from Pokémon cross dress as ballet performers and wedding couples. In the manga and anime Ouran High School Host Club, the main character of Haruhi Fujioka cross dresses as a boy so that she can work in a host club to pay off a debt she owes to the other members. Haruhi's father, Ranka, is also a cross dresser. In the manga and live action series of Hana Kimi (Hanazakari no Kimitachi e), the main character, Mizuki Ashiya, cross dresses as a boy to attend an all boys boarding school to meet her idol, Izumi Sano. In the manga and anime Shugo Chara, Nagihiko Fujisaki cross dresses as his "twin" Nadeshiko out of family tradition. He also cross dresses in his transformation Yamato Maihime. In the manga and anime Mermaid Melody Pichi Pichi Pitch Pure, one of Michel's servants named Lady Bat, who cross dresses as a female, is actually a male. In the anime and manga Hetalia: Axis Powers, Poland is a man and dresses like a woman sometimes. In the anime Himegoto, the main character, Hime Arikawa, cross dresses to join the Student Council who promises to pay off the debt created by Hime's parents. There are also four other characters who cross dress, including Hime's brother, Kaguya, HIro Toyotomi, No. 1, and Mitsunaga Oda, all of whom are against the Student Council.