"Transamerica" and "Boys Don't Cry" are the only movies I have ever saw about a transgender person. They are extremely different movies. Made six years apart, you can see the progression of our movement in how different these movies treat the subject.
"Boys Don't Cry" won an Oscar for Hilary Swank's heartbreaking performance as Brandon Teena, but following a tradition in Hollywood, the transgender character would be played by the opposite gender of what the character was. Hilary is a woman who was playing a man. I guess at the time it was not thought of that a male actor would play Brandon.
"Transamerica" is completely different. Felicity Huffman, a mainstream television actress, who kinda represents the average, white, suburban, middle-aged American woman, a mainstream mom if you want to call her that, took on a role that nobody ever thought she'd play, and the result was a brilliant performance that I feel should have won the Oscar, but the Academy being nearly 100% white, male, and straight and having hardly any education about transgender people to understand why it was such a good performance, passed it over. She did however win a Golden Globe and was considered the dark horse. (The winner that year was Reese Witherspoon for playing June Carter Cash in Walk the Line. I've seen both movies and Felicity's performance is more memorable, imo.)
Anyway, these are the two movies I've seen come out of Hollywood regarding transgender people. The earliest I think was "The Christine Jorgensen Story," which I can only imagine was a piece of sensationalist 50s claptrap... but maybe I'm wrong, I've never seen it. Then there was a TV movie called "Second Serve," about Renee Richards... Vanessa Redgrave played her I think, which was progressive casting for the time.
There was a movie in 2003 called "Normal" with Tom Wilkinson realistically playing a transgender woman who for most of the movie was a man. That casting fit because it wasn't depicting a post-operative person, it was really about him telling his wife and family. I remember seeing it and that it was very well done.
"Soldier's Girl" came out the same year. At the time it came out (2003 i think), the most famous transgender woman in America was Calpernia Addams. She hasn't been heard much since, but I remember that she was quite a role model for me back then when I was a teenager and was beginning to research transgender on the Internet. I didn't like that the Calpernia Addams character though was played by a man, Lee Pace. His performance must have been good because he was nominated for several awards, as was the movie itself.
Well what I'd like to know is:
1. How do you all feel about having male actors play transgender women, and vice versa? Does it bother you?
2. What was your reaction to "Boys Don't Cry," "Transamerica," and any other movie you saw?
3. What was the first movie you ever saw about transgender people? Was it a good experience or a bad one, and did it help you realize you were trans?