The Crying Game (1992)

Six-time Oscar nominee — and one-time winner — Neil Jordan's The Crying Game stars Forest Whitaker, Stephen Rea, Jaye Davidson and Miranda Richardson. The psychological thriller/drama follows Fergus (Stephen) and the unexpected romance sparked between him and Dil (Jaye), the trans girlfriend of his pal Jody (Forest). The film was praised for challenging the perceptions held about transgender people, while simultaneously encouraging audiences to empathize with the story's trans character by demanding more than sympathy.