Sean Penn, ‘Milk’

'Brando of our generation' brings powerful story to life

Gus Van Sant had more than a decade to think about the perfect actor to play Harvey Milk. Van Sant was an early choice to direct a biopic based on Randy Shilts’ “The Mayor of Castro Street,” a project whose producers fantasy-cast everybody from Daniel Day-Lewis to Robin Williams, Kevin Kline, Steve Carell and Kevin Spacey.

As “Mayor” went about its lengthy (and expensive) development process, the opportunity slipped away, but Van Sant’s interest in the San Francisco city supervisor and gay rights activist was piqued. So, when an original screenplay about Milk (based on fresh

research, rather than Shilts’ book) surfaced, Van Sant went straight to Sean Penn with the script.

“He’s like the Brando of our generation,” the director explains. “I had talked to him about it in the ’90s. He was an early desire, and he just went for it right away.”

Penn had played a politician once before in “All the King’s Men,” though the role of Milk was unlike anything on his resume of brooding, surly, even hurly-burly performances. In contrast with Penn’s hot-headed on- and offscreen persona, Milk was magnetic, jocular and unapologetic about his sometimes less-than-butch mannerisms that called for the actor’s most dramatic transformation since “I Am Sam.”

“It’s amazing to see this man who’s quite different in person become Harvey Milk — this really warm, sweet, jovial man,” says screenwriter Dustin Lance Black. “Early on in the shoot, people like Cleve Jones and Anne Kronenberg wanted to see the first day that Sean cut his hair and got into the suit. As soon as Sean turned the corner dressed like Harvey, with that haircut, walking like Harvey, Cleve Jones had to leave the set and go smoke a cigarette. To the people who really knew Harvey, it was uncanny.”

Though Penn wasn’t interested in doing a strict impersonation, Van Sant and Black provided him with an abundance of material documenting the real Milk — there was TV footage reflecting his charismatic public self as well as more intimate recordings (including the haunting will in which Milk predicted his own assassination) that showed a more reserved private persona.

Van Sant trusted Penn completely — “I just wanted him to create something that he wanted to create,” he says — marveling at how naturally the actor melded with the role. “He was really good at giving all the speeches, probably because he had spoken a lot in public and given political speeches himself.”

Coming attractions Penn’s next film is “Crossing Over,” co-starring Harrison Ford. Also, he and Brad Pitt are co-starring in Terrence Malick’s “The Tree of Life.”

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