It can be incredibly difficult to find good quality LBGT cinema, especially when the only kind that exists is typically just two white straight looking gay men who fall in love and usually die of AIDS. That being said, movies that portray lives of trans* people are hard to come by... but I have compiled a (short) list of my three favorite ones, along with descriptions that won't spoil anything, I swear.
1. Boys Don't Cry (1999) - A classically sad movie, this film chronicles the real life story of Brandon Teeva (Hilary Swank), who becomes involved with a beautiful girl who doesn't know that he's trans*. This film should absolutely not be watched if you are faint of heart, because it primarily focuses on the hardships he faces when it is discovered that he is trans in a society that considers him perverted. Seriously. You WILL cry watching this film.
2. Tomboy (2011) - This film is far less heart wrenching, but still is not a happy-go-lucky film. Mikael is a young trans boy, probably no older than eight, who finds himself hanging out with his friends and younger sister in a group that accepts him as a man and doesn't ask any questions. Despite hiding his true identity from his guy friends, his relationship with his sister is heartwarming and strong.
3. Boy Meets Girl (2014) - My favorite movie BY FAR. This movie is funny, insightful, and pushes a good message following fashionista Ricky and her best friend Robby. Ricky is played by Michelle Hendley, who is a trans woman actor, making this movie the only one on the list that has a trans person playing a trans person, and I think that speaks volumes for the content of this film. If you cry watching this movie, it'll be because of how happy of an ending Ricky experiences!