Good question. I guess my tastes have changed. I hadn't really thought about it.
I used to like some cross-dressing movies (they're almost all comedies) in which the main character crosses the gender line to get a job or get into the dream school or whatever. Those characters weren't transsexuals. It's kind of annoying that they get to go back to their nice normal life at the end of the movie (and I don't), but I don't mind watching these films occasionally, even now.
I tend not to like transsexual movies. It used to be, I always wanted to see them, but then I didn't want to watch them twice. I wasn't particularly unhappy with Boys Don't Cry, but Brandon Teena was kind of a jerk. Anyway, I won't watch it again. I didn't care for Normal at all (a couple of non-trans people have raved about it to me), and I really hated Transamerica. Soldier's Girl was pretty good but so depressing.
I've seen a few of the more recent documentaries, and I'm never happy with them. That one whiny guy on Boy I Am spoiled that movie for me, and I didn't like any of the people in Transgeneration. Yet I still felt honor-bound to watch the whole damned series.
I don't go out of my way to watch transsexual movies anymore. But I have to admit that I'm curious about the new Glenn Close movie, partly because I like Close's work and partly because the setting is my era of specialty. But I don't think I'll see it.
I wouldn't mind seeing a docudrama on Lou Sullivan, though.