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Films with theme "Transgender in film", sorted by production date

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Yankee Doodle in Berlin
Yankee Doodle in Berlin (1919)

Directed by F. Richard Jones
Origin USA
Genres War, Comedy
Themes Films about sexuality, LGBT-related films, Transgender in film, Political films, LGBT-related films, LGBT-related film, Cross-dressing in film
Actors Ford Sterling, Ben Turpin, Malcolm St. Clair, Bert Roach, Charles Murray, Marie Prevost

Captain Bob White, an American aviator behind enemy lines, disguises himself as a woman in order to fool and steal an important map from the members of the German High Command, including the Kaiser himself.
Good Night, Nurse!
Good Night, Nurse! (1918)
, 26minutes
Directed by Roscoe Arbuckle
Origin USA
Genres Drama, Comedy
Themes Films about sexuality, LGBT-related films, Transgender in film, LGBT-related films, LGBT-related film, Cross-dressing in film
Actors Roscoe Arbuckle, Buster Keaton, Al St. John, Kate Price, Alice Lake, Joe Bordeaux

Lassée de son mari alcoolique et ayant lu une annonce publicitaire dans un journal, la femme de Fatty traîne ce dernier à la clinique pour y être opéré afin d’être définitivement débarrassé de l’envie de boire. Mais une fois dans la place, ce dernier n’a de cesse que de s’enfuir.
I Don't Want to Be a Man
I Don't Want to Be a Man (1918)
, 41minutes
Directed by Ernst Lubitsch
Genres Comedy, Romance
Themes Films about sexuality, LGBT-related films, Transgender in film, LGBT-related films, LGBT-related film, Cross-dressing in film
Actors Ossi Oswalda, Curt Goetz, Margarete Kupfer, Victor Janson

High-spirited young Ossi Oswalda is the bane of her uncle and governess' existence. She insists on playing poker and smoking and talks with strange men on the street. When her uncle leaves to take up a new job, she looks forward to enjoying new freedom. Her hopes are dashed when her new guardian Dr. Kersten proves to be strict and unyielding. Frustrated with her cloistered life, Ossi sneaks out on the town dressed as a young man. She finds that being a man has its own disadvantages when she discovers she is not given the same gentle treatment when she is masquerading as a male. She decides to attend a lavish ball in her new disguise. Soon, Dr. Kersten appears at the ball trying to woo a young lady and Ossi vengefully tries to steal her away from her hated guardian. Eventually, another man attracts the woman's attention, and the disguised Ossi and the doctor reconcile. The two proceed to bond over cigars and champagne. After the ball is over, the pair drunkenly stumble home, exchanging inebriated kisses. After they pass out in a hired cab, the driver mistakenly leaves Ossi at the doctor's house and drops off the doctor at Ossi's home. Upon waking up in strange house, Ossi becomes alarmed and runs home where the doctor has woken up and is trying to sneak out of the house undetected. Still in disguise, she pretends she is visiting her cousin Ossi and the doctor begs her not to tell his ward about their "adventure". Ossi agrees and goes upstairs where she begins to undress. The doctor comes in to wake her and is astonished to see Ossi wearing a man's suit. The tables are turned when Ossi scolds him for his behavior. Giving in to the attraction he feels for her, the doctor kisses her.
The Butcher Boy
The Butcher Boy (1917)
, 24minutes
Directed by Roscoe Arbuckle, Neil Jordan
Origin USA
Genres Comedy
Themes Films about sexuality, LGBT-related films, Transgender in film, LGBT-related films, LGBT-related film, Cross-dressing in film
Actors Roscoe Arbuckle, Fiona Shaw, Eamonn Owens, Buster Keaton, Stephen Rea, Al St. John

The story involves Arbuckle working as the butcher boy in a country store. He falls in love with the cashier, who is the daughter of the store owner. He follows her, disguised as a female cousin, to an all-girl boarding school.
Coney Island
Coney Island (1917)
, 24minutes
Directed by Roscoe Arbuckle
Origin USA
Genres Comedy
Themes Films about sexuality, LGBT-related films, Transgender in film, LGBT-related films, LGBT-related film, Cross-dressing in film
Actors Roscoe Arbuckle, Buster Keaton, Al St. John, Jimmy Bryant, Joe Bordeaux, Alice Mann

The twenty-four minute film follows Arbuckle's antics at Coney Island, the New York City amusement park and beach resort, where he sneaks away from his wife to enjoy the attractions, gets a rival for another woman arrested, and disguises himself as a woman. The Keystone Kops are also featured.
The Masquerader
The Masquerader (1914)
, 16minutes
Directed by Charlie Chaplin
Origin USA
Genres Comedy
Themes Films about sexuality, LGBT-related films, Transgender in film, LGBT-related films, LGBT-related film, Cross-dressing in film
Actors Charlie Chaplin, Roscoe Arbuckle, Chester Conklin, Charles Murray, Ben Turpin, Fritz Schade

The Masquerader is a comedy short film, that is about making films at Keystone. Charlie plays an actor who bungles several scenes and is kicked out. The next day a strange beautiful woman appears to audition for the film, it's Charlie in drag. After doing a perfect impersonation of a female, Charlie has drawn the attention of the director and is hired to act in his films. The director gives the beautiful woman the mens dressing room to change in and to Charlie's mistake he returns to his tramp costume. When the director returns, looking for the woman, he finds Charlie and that he has been tricked. Angry, the director chases Charlie through the studio until Charlie decides to jump into what he thinks is a prop well. The film ends with the director and other actors laughing at Charlie as he is trapped in the bottom of the well. The plot involving a man dressing up as a woman is quite popular in old silent movies.
Raja Harishchandra
Raja Harishchandra (1913)
, 40minutes
Directed by Dhundiraj Govind Phalke
Origin Inde
Genres Drama, Historical
Themes Films based on mythology, Films about religion, Films about sexuality, LGBT-related films, Transgender in film, Mythologie hindoue, LGBT-related films, LGBT-related film, Cross-dressing in film
Actors D. D. Dabke or Dattatraya Damodar Dabke, Anna Salunke

The film opens with a scene of a tableaux patterned on the painting by Raja Ravi Varma, of Raja Harishchandra and his wife with their son. The film revolves around the noble and righteous king, Harishchandra, who first sacrifices his kingdom, followed by his wife and eventually his children to honour his promise to the sage Vishwamitra. Though, in the end, pleased by his high morals, the Gods restore his former glory, and further bestow him with divine blessings.
In a Garden
In a Garden (1912)

Directed by Shaji Kailas
Genres Drama, Romance
Themes Films about sexuality, LGBT-related films, Transgender in film, LGBT-related films, LGBT-related film, Cross-dressing in film
Actors Mammootty, Riley Chamberlin, Divyaa Unni, Murali, Marie Eline, Marguerite Snow

The film begins with some insight into a Brahmin family, with Patteri (Thilakan) as the patriarch, who is a great astrologer and helps a police officer(Janardhanan) crack a robbery case. The story then moves on to a political arena, where Madhavan (Balachandra Menon) is selected as the Chief Minister. He is popular with the people and but his self serving ministers and his own party is rebelling against him. Madhavan has to win the by-election to retain his position as chief minister. During a chance encounter with Patteri (Thilakan), Patteri predicts the by-elections won't happen.