Penn won the 2008 Best Actor Oscar, his second after winning in 2003 for "Mystic River," for his portrayal of Harvey Milk. Milk was elected to the San Francisco Board of Supervisors in 1977, making him the first openly gay man to be elected in California. Milk was also an activist for gay rights. "Penn at first seems like a caricature – a theatrical conceit," Rainer wrote of Penn's performance. "But he grows into the theatricality and gives it a human dimension. He gives us a long look behind the mask."
