Hey, just out yeterday on was "Breakfast on Pluto". We have a thread about it elsewhere, but to summerize, IMO it is a better movie than Transamerica. Made by the same director of "The Crying Game."
Another DVD (a documentary) is "Trans Generation". This is a seven part series made for the Sundance Channel and it is surprisingly good. No doubt this will be on many pre-op's required viewing.
Both movies get 2 BIG THUMBS UP from me. (I already own these two!)