The earliest cross dressing film in the British Film Catalogue is; Oct 1898, BFC 00157. Title; "ALLY SLOPER" (75ft-1.5ft per second); d. G A Smith. Synopsis; Man dresses up as woman, then film is reversed.
In Novemeber 1900, Phono-Bio-Tableaux Films released a series of 3 minute short films with, among others, Vesta Tilley, the male impersonator. These 9 films were the first British sound films,being synchronised to gramaphone records. Vesta Tilley sang the following; "The Midnight Son", "Algy the piccadilly johnny", and "Louisiana Lou",BFC 00390.
In April 1907 Miss Tilley appeared in the following Chronophone film series, again sync. to gram. records, singing "Please conductor,don't put me off the train", BFC 01547.
A Vesta Tilley Bio-pic was filmed in 1957.
The following may also be of interest.
SLINTERS, Dec 1929, BFC 07826. Synopsis; France,1916. Soldiers form concert party. Among the acts was Reg Stone, Female Impersonator, who sang"I'll be getting along", and "There's room in my heart".
SKIMPY IN THE NAVY, BFC 10383. Synopsis;Friends join navy to seek treasure on Mediterranean island. The film featured Vic Ford And Chris sheen, drag artists, who sang "Nobody loves a fairy when she's forty". Nov. 1949.
A LITTLE OF WHAT YOU FANCY, BFC non-fiction catalogue 12179.
Synopsis; History of the music hall. The film featured Barry Chat and Terri Gardner, drag artists, who sang; "Why do they always say no?", "Somebody loves me", and "I wonder where my baby is tonight?".
The following British films are all about the Transgendered.
BOYS FROM BRAZIL. 1993, B.B.C. DOC.
THE CRYING GAME. 1992.
EAT THE RICH. 1987.
I WANT WHAT I WANT. 1971.
JUST LIKE A WOMAN. 1994.
LADY BOYS. 1992 CHANNEL 4 DOC.
LILY SAVAGE LIVE - PAYING THE RENT. 1993, COMEDY VIDEO.
A LITTLE BIT OF LIPPY. 1992. MADE FOR TV.
ORLANDO. 1993.
PRIVATES ON PARADE. 1984.
SEX CHANGE - SHOCK! HORROR! PROBE!. 1989. CHANNEL 4.
SHINJUKU BOYS. 1993. DOC.
STONEWALL. 1995. US/GB CO-PRODUCTION.
TRIPLE ECHO. 1972.
The above is a small amount of the information I have on this subject, and, as time permits I will contribute more. If anyone is interested in any of the above, then please message me for more details, though, because of other commitments, I may be slow in replying.
Elly H.