Gendernauts: A Journey Through Shifting Identities (1999) is available free to stream on Netflix (now through May 26th, 2013). Some parts of this movie may strike one as rather dated (in terms of terminology, descriptions, or otherwise) or potentially problematic - still, there is much of interest and, I think, much to be gained from watching.
Description: Monika Treut’s provocative documentary explores the little-known world of transgenderism through profiles of several “gender cyborgs” living in the San Francisco Bay Area. In candid interviews, Treut’s subjects share their personal experiences, their perspectives on gender and their plans for the future. The film also delves into the options — and challenges — gender-bending hormone treatments and surgeries provide.