This is part of the Queer Film Blogathon hosted by Caroline over at Garbo Laughs.
Transgender people have featured in exploitation films since at least the 1930s. There's a hermaphrodite in the circus in Tod Browning's Freaks, though ze doesn't play a prominent role in the film. There's also a genderqueer element to James Whale's horror comedy, The Old Dark House, in which the patriarch of the film's looney family is played by a woman in old man drag. Whale liked to tweak gender norms in his movies sometimes. The golden era of transgender exploitation began in the 1950s, though, when Christine Jorgensen's gender surgery became a seven day wonder. One of the first films to take on the subject of transgenderism was Ed Wood's legendarily bad Glen or Glenda (1953, aka: I Changed My Sex). It's easy to mock Wood and Glen or Glenda, what with its weird assemblage of stock footage and with Bela Lugosi playing a god who composes boys and girls out of snips and snails and sugar and spice, to say nothing of its litany of angora sweaters and grossly misinformed pronouncements on the causes of transgenderism. Hell, you can even play the transgender documentary drinking game while watching it (Glen or Glenda is a documentary of sorts, after all).
What's that? Transgender documentary drinking game? Oh, yes. The tropes of the trans documentary are so calcified that you can get good and sloshed if you follow along with alcohol. The original version was authored by Gwendolyn Ann Smith, and you can read it here. Others have added to it over the years.
Anyway...