It occurred during filming of a crucial scene in Gus Van Sant's multiple-Oscar-nominated biopic " Milk," which stars Penn as the former San Francisco supervisor, one of America's first openly gay elected officials.
After honing his political skills as a flamboyantly courageous, bullhorn-toting community organizer, the so-called Mayor of Castro Street decided to run for office. He shed his aging-hippie couture, cut off his ponytail and took to wearing conservative suits, the better to reassure anxious Pacific Heights matrons that he was a serious candidate.
When Penn emerged on set one day in that incarnation, ready for filming, Jones was struck by the actor's uncanny resemblance to his beloved friend and mentor.
"That was the day it all came together and Sean, like, had this direct line to Harvey," says Jones, a longtime Bay Area gay rights and labor activist who served as a consultant on the movie and appears in three cameos, in addition to being portrayed in "Milk" by actor Emile Hirsch.
"It was weird," Jones continues. "It was eerie and wonderful and at times just incredibly sad."
Judging by the evidence of Oscar voting, a number of factors harmonically converged in the making of "Milk." In Van Sant, the movie found a director capable of imparting a resolutely independent vision to a film that's intended to play as well on Main Street as on Haight Street.
In Dustin Lance Black, it procured a screenwriter able to humanize and dramatize an opera-sized chapter of American social history.
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And with such supporting actors as James Franco, Diego Luna and the Oscar-nominated Josh Brolin as Milk's political rival and eventual assassin, Dan White, along with Danny Elfman's inventive musical score, the filmmakers were able to conjure not only one man's remarkable story but also the turbulent sensibility of a mind-blowing epoch.
Still, none of these contributions would've added up without a lead actor who could bring focus and verisimilitude to Milk's ebullient, prismatic personality, an actor who could embody, rather than merely impersonate, the actual man.
Enter Sean Penn.
"I don't think anything could've prepared us for what he brought to the screen," says Bruce Cohen, who produced the movie with Dan Jinks.
"What we've heard from so many people is, you forget you're watching Sean Penn," Jinks concurs.
When White's bullets struck down Milk and San Francisco Mayor George Moscone on Nov. 27, 1978, America lost not only one of its most intellectually nimble and socially progressive politicians, it also lost a man whom Jones calls "one of the most empathetic people I've ever met." Among those who knew him best and worked with him most closely, Milk was cherished not only for his relentlessly determined leadership but for his wit, sensitivity and grace under pressure.
No one associated with the film doubted Penn's ability to meet the role's enormous technical demands -- indeed he is among the film's Oscar nominees. Besides his professional credentials, he brought to the table other experiences as a political activist and occasional globe-hopping journalist that made him seem a natural fit to play Milk.
Van Sant says that during the casting process, he watched a number of YouTube videos showing Penn giving speeches at town hall meetings and in other forums, demonstrating his oratorical flair and charisma.
"I think a lot of it was aimed at Bush and the Iraq war," Van Sant says. "He was funny, he was also daring and also accurate and extreme, which are a lot of things Harvey was. We were very inspired by his talks."
As part of his research process, Black interviewed more than 40 people who had known Milk in various capacities. His screenplay provided Penn and the other actors with the foundations of authenticity on which to construct their roles.
"He and I talked about the ideas somewhat," Van Sant says of Penn, who wasn't available for interviews, "but I think he kind of assimilated his character through studying Harvey and using his imagination and willing it into being."