The Lost in Transgender blog has a lot of content on movies with a transgender theme or transgender roles.
In the latest article Cheryl writes about the Japanese movie "Funeral Parade of Roses":
Funeral Parade of Roses is a very unusual yet fascinating movie directed by Toshio Matsumoto in 1969. Clearly an experimental film, yet it’s so much more, offering a unique insight into a hidden subculture of Japan in the late 1960s.
Funeral Parade of Roses can be classified as a surreal, transgressive, avant garde and a queer punk drama, with documentary inserts, Cheryl writes.