Legendary New York producer Christine Vachon takes us on the journey of the controversial 1999 film Boys Don't Cry. At the time, films about trans people were rare and very few trans actors were comfortable being out, which led to the casting of Hillary Swank in an Oscar-winning performance. The film took seven years to come to fruition and that time was fraught with legal battles, lack of money, and competing projects from more established filmmakers, but Kimberly Pierce's exacting vision and Hillary's incredible performance led to a film that resonates to this day.