I was going through a stack of photos recently and came across a picture of a Hollywood home owned by Julian Eltinge. Eltinge was the most successful 'female impersonator' during the 1910s-1920s. He became one of the highest paid performer of his day. He even had a theatre named after him in New York and published his own magazine of beauty tips for women.
Making his fame on Broadway, Eltinge moved to Hollywood and made about 15 films. He owned a beautiful mansion in the Edendale (Silver Lake) area north of Los Angeles. In 1918 he made Over the Rhine. Rudolph Valentino played a role in that 1918 film which was re-edited and re-leased as a comedy called The Isle of Love in 1922.
By the 1930s, Eltinge fame faded. The depression, the decline in stage shows and his age, all played a role. He died in 1941.
On the web I found a documentary being made about his life and career called The Julian Eltinge Project. The site has a list of stage performances and films, which includes postcards from different parts played. There are more images here at Silent Gents.
As for Chaplin, he played a woman on screen three times: A Busy Day (1914 Keystone), The Masquerader (Keystone 1914) and A Woman (Essanay 1915). Edna Purviance played a male part once in Behind the Screens (1916). She was trying to find work as a handyman at a studio.
Turner Classic Movie is running a special series called Screened Out: Gay Images in Films. The series plays Monday and Wednesday through the month of June. The series starts with some rarely seen silent films on Monday night, June 4th.