Pair an effusive and extroverted, larger-than-life politico like Harvey Milk complete with community-forging charisma, panoramic outlook, and labyrinthine City Hall machinations with a reserved, perpetually-outside-looking-in independent, à la director Gus Van Sant? That feature-film odd-coupling might have understandably strained some brains in Hollywood. Making the seldom-seen moments of otherwise-secret or neglected lives visible has seemingly been Van Sant's calling, and his most memorable films 1985's Mala Noche, 1989's Drugstore Cowboy, 1991's My Own Private Idaho, 2003's Elephant, and even the Oscar-gathering 1997 Good Will Hunting have relied on his coolly unblinking, surprisingly cerebral yet gently empathetic eye, whether focused on Mexican immigrants, '70s-era oblivion-seekers, Northwestern hustlers, a hidden savant, or disaffected teenagers.
Still, those leitmotifs entwined with Van Sant's terrible, tangible sense of romance with his outsiders, artists, and lost souls, as well as the way his camera seems to fall head over heels for his characters made Van Sant a natural to make Milk, after Oliver Stone's aborted feature-film attempt to tell the slain San Francisco supervisor's story. "There is always that question: why I haven't done a film like this earlier," Van Sant confessed, clearing his throat for the umpteenth time while agreeing that he hasn't ever quite done a film like Milk. "Yeah, I hadn't done a big movie, so there were people around who were like, 'Can you handle it? Can it be done?' They think that way. Since there was no business model, they were like, 'No, he can't, because he makes these scruffy, little movies. Too big a gamble, you know.'
"That's a part of Hollywood, but it's kind of like safe bets: it can make bad stuff happen as easily as good stuff, and it has its own closed policies like the old conservative City Hall-type policies. 'New supervisors who haven't handled the job before are incapable and they're screwing things up.'"
Thankfully the gamble paid off and the tale of California's first openly gay politician has been told with elegance, poetry, and not a little heart-stirring, inspirational grace, by the man whom biographer James Robert Parish describes as "the standard bearer of America's 'queer cinema'" one who fuses extreme close-ups, handheld shots, and found footage in a collaborative, textural approach that lends a Kodachrome pop-culty feel to his films. The process makes for "beautiful pictures every time," as a windblown Sean Penn put it at a Ritz Carlton press conference after Milk's Oct. 28 world premiere at the Castro Theatre.
Seated at the middle of a long table between Penn and Josh Brolin, who portrays Milk's killer Dan White, as they traded friendly jabs, Van Sant remained mostly silent physically at the center, but an observer apart at the same time. Later in a hotel suite, face to face with a single interviewer, the director seemed equally out of place, folded uncomfortably into a plush chair, arms tightly crossed over a tan jeans jacket sporting a "No on 8" sticker, with a small, nylon, bright-blue dollar-store-style backpack by his side. He more closely resembles a 56-year-old teacher or elder-care worker than a Hollywood insider.
The latter role is evidently still alien to him. His first brush with Milk came in 1978 while he was driving across the country and heard on the radio that the supervisor was shot. Though he later saw the 1984 documentary The Times of Harvey Milk, it never occurred to him to make a film about the politician. "It seemed like a very big story," Van Sant said. Mala Noche and Drugstore Cowboy "were stories that were devised to be made with really low budgets, like $20,000.