Glen or Glenda

Ed Wood’s magnum opus. From Wikipedia:

Glen or Glenda is a 1953 drama film written, directed by, and starring Ed Wood, and featuring Bela Lugosi and Wood's then-girlfriend Dolores Fuller. The title was originally I Changed My Sex! and is often given as Glen or Glenda? but the question mark is not present in the film itself or on its poster.

The film is a docudrama about cross-dressing and transsexuality, and is semi-autobiographical in nature. Wood himself was a cross-dresser, and the film is a plea for tolerance. It is widely considered one of the worst films ever. However, it has become a cult film due to its low-budget production values and idiosyncratic style.