#16. Shakespeare in Love
Oscar Wins: 7
Oscar Nominations: 13
Release Year: 1998
What happens when William Shakespeare’s own love life is fictionalized in a way only the Great Bard could pull off? You get “Shakespeare in Love,” the 1998 winner of best picture, best actress and best-supporting actress (for Gwyneth Paltrow and Judi Dench, respectively). Broke and struggling, the young writer strikes up a romance with a young woman, who acts as his muse for what would become “Twelfth Night.”