John Cameron Mitchell brings his cult musical about "internationally ignored" transgender rock star Hedwig to the screen. Boys Don't Cry was originally given an NC for even addressing trans issues, but was later downgraded to an R. Peter Jackson was journeying through fantasy worlds long before Lord of the Rings —albeit one conjured up by two very real New Zealand school girls played by then-newcomers Kate Winslet and Melanie Lynskey who escape their own realities through their imaginations. Shot on iPhones along Santa Monica Boulevard's unofficial red light district, Tangerine follows two transgender sex workers and one lovesick cab driver through a particularly eventful Christmas Eve. What begins as a contentious friendship turns into a full-blown love affair as the two young men spend their idle summer days in the lush Mediterranean locale, bracing themselves for an inevitable heartbreak.
Skylar. Age: 26.
Amazon iTunes Gus Van Sant's loose Shakespearean adaptation brought the New Queer Cinema movement into the mainstream, with River Phoenix as a young, narcoleptic hustler and Keanu Reeves as his best friend and unrequited love interest.
Kaylin. Age: 29.
The 50 Best LGBTQ Movies Ever Made
If any film can be credited with kicking off our cultural conversation on gender, this is it. The Biggest Movies to Look Forward to in Amazon iTunes The life of Cuba's "transformistas" is captured beautifully in this father-son story about a boy who wants to perform drag and his father, newly released from prison and unable to accept who his son is.