 Linda Hunt (qv) is the only actress ever to win an academy award  playing a man, no cross dressing or gender confusion involved.  Hilary Swank (qv) (_Boys Dont Cry (1999)_ (qv)) received the  award for playing a biological female who identifies as a man.  Gwyneth Paltrow (qv) (_Shakespeare in Love (1998)_ (qv)) received  one for playing a woman who was pretending to be a man pretending to  be a woman.