The DVD of Boys Don't Cry contains footage of Hilary Swank, who played Brandon Teena, saying how ey's playing the role as a confused lesbian. I couldn't help but cringe as the whole point of the film was that it was based on the true story of a transman who was a straight man who happened to be bio-female. The fact that the person portraying the main character didn't understand at all the person in real life who that character was based on made me wonder if they were the best person for the job.
Maybe it's just me, but I think films based on true stories should involve a cast that actually understands the true story in the first place.
Sorry about the rant.
(Incidentally, Ma Vie en Rose is generally considered a better transsexual film, but isn't as widely known, perhaps because it wasn't made in America and the dialogue is in French. The protagonist in it is a kid, possibly to help dispel the myth that transsexuality is a sexuality.)