Gun Hill Road has a trans woman actually playing a transwoman in Harmony Santana. The film has been making the rounds in the various TBLG film festival circuit including Houston's, which I missed (darn it) because I found out about it too late..
Gun Hill Road is being released this weekend and really looking forward to seeing it at my favorite multiplex.
But the person I'm most happiest for is Harmony, who got the opportunity to play this character with Esai Morales, Judy Reyes and some other kick butt actors. Here's the video of her interview from the 2011 Sundance Film Festival.