The Real Person: Harvey Milk was the first openly gay politician to be elected to public office in California, as a Public Supervisor in San Francisco. His outspoken activism helped to improve gay rights, before he was assassinated in 1978.
The Actor: Sean Penn had survived his 1980s bad boy image (and marriage to Madonna!) to become one of the finest actors of his generation. He already had one Oscar under his belt for Mystic River when he played Harvey Milk in the Gus Van Sant film Milk; that role brought him a second.
Most Stunning Element: It seems Penn and Madonna are still on good terms, as he was compelled to text her following his on-set kiss with co-star James Franco. "I just broke my cherry kissing a guy," Penn wrote. Madonna's reply: "congratulations."