I just found a movie that may be kind of transgender at least it's about cross dressing.
Convinced that she is not being taken seriously because of her looks, a pretty teenage girl enrollsin a new high school disguised as a boy, setting off a chain of events leading to comic hysteria, and more than a little social awareness
Though marketed as a raunchy teen sex comedy à la Porky's, Just One of the Guys is an amusing and well-acted comic riff on gender roles. Believing that she's lost a journalism contest because she's a woman, high school student Joyce Hyser disguises herself as a boy in order to see how the other half lives. Her investigation leads her to discover some interesting truths about how men and women treat each other in social and romantic situations. The screenplay by coproducers Jeff Franklin (a veteran TV scribe) and Dennis Feldman nicely balances the sex-driven gags with more character-driven material, which is well delivered by Hyser, Clayton Rohner as her eccentric pal, and especially Billy Jacoby as her perpetually aroused brother; the capable cast also includes Sherilyn Fenn and Arye Gross. Eighties music fans should also appreciate the soundtrack, which features tracks by Berlin, Lindsay Buckingham, and the Stooges. --Paul Gaita
