Milk is an Academy Award winner.
Milk (film) . Ultimately , it received eight Academy Award nominations , including Best Picture , winning two for Best Actor in a Leading Role for Penn and Best Original Screenplay for Black . Attempts to put Milk 's life to film followed a 1984 documentary of his life and the aftermath of his assassination , titled The Times of Harvey Milk , which was loosely based upon Randy Shilts 's biography , The Mayor of Castro Street ( the film won the Academy Award for Best Documentary Feature for 1984 , and was awarded Special Jury Prize at the first Sundance Film Festival , among other awards ) .