The story of Harvey Milk, who rose to prominence in San Francisco first as an outspoken community activist and later as a member of the city’s Board of Supervisors, has long tantalized directors eager to capture his odyssey on the big screen. And though the first openly gay man elected to public office in America inspired an Oscar-winning documentary – 1984’s The Times of Harvey Milk – a second cinematic tribute has remained little more than an on-again, off-again rumor since his death three decades ago.

Now, the self-styled Mayor of Castro Street will be portrayed in Gus Van Sant’s Milk, which tracks the Long Island, N.Y., native from his move to San Francisco in 1972 to his assassination, six years later, at the hands of onetime Board of Supervisors colleague Dan White. (Surprisingly, another Milk biopic, courtesy of Superman Returns director Brian Singer, is tentatively due in early 2009.) But getting Milk into theaters represented an uphill battle.

“Several industry folks told me to forget about it, that it was too risky,” says screenwriter Dustin Lance Black, who was moved to tears by his first viewing of The Times of Harvey Milk and began research for a possible script by consulting with longtime Milk confidant and San Francisco AIDS Foundation co-founder Cleve Jones.

“It took a lot to convince some of Harvey’s real-life contemporaries that I was someone who could make this happen, that they weren’t wasting their time. I made these assurances, but I wasn’t really sure I could pull it off. Some of [these people] became like family to me and confided some painful memories. I was terrified of letting them down. But, I thought, we have to get his story out there, we’ve got to continue his message.”

It was Jones who facilitated a meeting between Black and Van Sant, the art-house auteur responsible for 1991’s My Own Private Idaho and, more recently, Elephant, his stark recreation of a Columbine-style killing spree. To him, the opportunity to tell Milk’s story to a generation unfamiliar with his fearless activism, at a time when resistance to same-sex marriage is coming from both conservatives and politically cautious liberals, was too tempting to resist.

“The Times of Harvey Milk set the bar pretty high, but I felt a dramatic version would be an important continuation,” Van Sant says. “Harvey is one of the more illustrious gay activists, and since he died in the line of duty he has achieved sainthood in the gay world. One reason to make this film was for younger people who weren’t around during his time, to remember him and to learn about him.”

Van Sant, whose track record remains mostly unblemished after 26 years behind the camera, didn’t have any trouble recruiting an impressive cast of in-demand actors – among them, Sean Penn, Josh Brolin and James Franco – despite graphic sexual content that some might consider high-risk. Whereas Mark Wahlberg once confessed to feeling “creeped out” by the sex scenes in Brokeback Mountain, a film he was initially considered for, Penn and Franco, who play Milk and his much-younger lover Scott Smith, embraced the physicality of their roles.

“There was no hesitation for me,” says Franco, a Palo Alto native who admits to knowing little about Milk before giving Van Sant notice that he was more than available for any part in the film. “I told Gus from the beginning that I’d do anything he wanted.”

“I subscribe to the it-only-hurts-the-first-time philosophy,” jokes Penn, who text-messaged ex-wife Madonna with the news that he’d “broke his cherry” after a sharing a passionate kiss with Franco on Castro Street before a throng of more than 200 enthusiastic spectators.

Of course, whether Milk shocks or titillates is of little concern to the filmmakers, who hope the movie’s political themes will resonate in a climate as turbulent today as it was 30 years ago. Back then, Milk famously railed against Proposition 6, a ballot initiative introduced by California state senator John Briggs that would have banned gays and their supporters from teaching in public schools. This Election Day, Californians voted on Proposition 8, which would outlaw gay marriages.

“Harvey came up against a lot of obstacles, which I think is the case for any gay man now,” says Brolin, who plays Dan White. “The irony is that Prop 8 is now what Prop 6 was then.”

“Watching this film, you’re watching a lot of very good-hearted human beings, and who and how they decide to f--- is irrelevant,” adds Penn. “I think that alone can [make people] less confused by [homosexuality]... less afraid of it.” Before the vote, he was at Symphony Hall and was startled to see protesters carrying signs reading “Matthew Shepard Burn in Hell.” The more the movie succeeds in showing the fullness and decency of its characters’ lives, he believes, “the less breathing room there is for that kind of thinking.”