As we approach the upper third of this list, we're coming across movies that have huge reputations and armfuls of awards. 'Boys Don't Cry' definitely fits that bill. Released in 1999, it's ostensibly an independent film but has a blockbuster profile, ultimately being picked up by Fox and distributed to all major cinemas.
'Boys Don't Cry,' as so many gay-themed films are, is based on true events. Hilary Swank is riveting as Brandon Teena, who ultimately pays for the search for her real gender identity with her own life after the men in her life refuse to accept her for who she is. The sad and beautiful movie tackles the tragedy of Teena's life head on, linking the personal tragedy with broader themes of empowerment, freedom and the right to live without judgment. Swank went on to collect the 'Best Actress' Oscar for her performance.