15. Boys Don’t Cry (1999)
Hilary Swank remains one of the youngest ever winners of the Best Actress Academy Award, and it was her performance as real-life transgender man Brandon Teena that won it for her. Teena identified as male but never underwent reassignment surgery, and in 1993, at the age of 21, he was raped and then murdered by two young men. Boys Don’t Cry is something of a modern classic, but the story it is based on is truly sobering.
14. Schindler’s List (1993)
While Steven Spielberg’s iconic World War II drama, Schindler’s List, depicts one of the more heroic tales to have come out of the Holocaust, even the brightest of endings is tragic when it’s set in the midst of such an unimaginable atrocity. The real Oskar Schindler was forced into hiding after the war and ended up jumping from country to country, almost destitute. In later life he suffered a heart attack, ultimately dying in 1974 at the age of 66.