Gus Van Sant has never been what you’d call a risk-averse filmmaker, but he directs his Harvey Milk biopic so carefully, there might be a Ming vase balanced on his head. Van Sant’s steps are deliberate, his posture is straight, his attitude is responsible, and his eyes are fixed firmly on the prize. (Only once does the filmmaker indulge in technological tomfoolery — shooting a scene as reflected in a metal whistle fallen to the pavement.) No less cautious, Sean Penn drops his habitual banty roosterism to play Milk (1930–1978), the martyred gay activist and San Francisco supervisor, with the concentration of an actor entrusted to portray the future subject of a U.S. postage stamp.

Opening 30 years and a day after Milk and San Francisco mayor George Moscone were gunned down in City Hall by another supervisor, ex-cop Dan White, Van Sant’s film is narrated by Milk from beyond the grave — less an exercise in fatalism than a way of giving collective history an engagingly Noo Yawk accent. The film is skillfully edited, using archival footage when necessary, and, working from a detailed script by documentarian Dustin Lance Black, Van Sant streamlines Milk’s life, simplifying his trajectory from closeted Wall Street zero to out-front Castro Street hero. On the eve of his 40th birthday, Milk picks up cute hippie Scott Smith (James Franco) exiting the subway and, after a romantic evening in tight close-up, effectively joins the counterculture, growing his hair and eloping with Smith to San Francisco. There, they open the Castro Camera Shop. When some cheerful canoodling prompts a local Chamber of Commerce type to blackball the enterprise, an activist is born: “We’ll form our own business association!”

This ringing declaration serves to announce San Francisco’s new gay district as an autonomous region with the Castro Camera Shop at its epicenter. It also allows the filmmakers to portray the burgeoning Castro as a function of Milk’s own political development. (The collective nature of this enterprise is built into the movie itself, which not only depicts but, in some cases, casts Milk’s associates.) Milk organizes against police harassment and, allied with progressive elements in the Teamsters union, helps to ban right-wing elixir Coors from the Castro’s bars. After San Francisco’s most powerful gay figure advises Milk to simmer down, the irrepressible entrepreneur appoints himself Mayor of Castro Street, hopping an actual soapbox to capture the attention of an unruly crowd: “My fellow degenerates.” Losing a run for San Francisco’s Board of Supervisors, Milk cuts his hair, shaves his beard and loses again, promptly launching an equally quixotic primary challenge against local state Assemblyman and future mayor Art Agnos (Jeff Koons, no less).

Scarcely less indefatigable, Penn is present in nearly every scene. His marked resemblance to Milk — hawkish profile, mask-of-comedy smile — is matched by an understanding of his gregarious character’s political gifts. The Mayor of Castro Street was a son of the Borscht Belt — a wise guy, a tummler, part self-deprecating nerd, part infectious showoff. (Like Harvey, Penn has no difficulty milking it.) More hearty frontier settlement than drag- and disco-fueled den of depravity, the Castro blossoms in the warmth of Milk’s sunny personality. A thousand flowers bloom: Abandoned by the long-suffering Smith, Milk gets a new campaign manager, self-described “tough dyke” Anne Kronenberg (pert Alison Pill); a new lover, Jack Lira (adorable Diego Luna); and, finally, a seat on the Board of Supervisors.

Happy, flirtatious, paternal, Milk was able to play politics both inside City Hall and out in the streets. San Francisco is the city Republicans love to hate and Milk turns grandly world-historical once the campaign launched by homophobic Christian crusader and Moral Majority avatar Anita Bryant arrives in the form of Proposition 6, an initiative to purge gay teachers (and their supporters) from public schools. The new supervisor finds himself on the front line of the Culture Wars, face to face with evil twin Dan White (Josh Brolin who, better directed here than in W., has the distinction of playing the year’s two preeminent real-life villains).

Beleaguered personification of “family values,” White is the film’s most complex character, after Milk. That their death match embodies a civil war in the American psyche is implicit in the script’s suggestion that White’s rage — as well as his fascination with Harvey — is fueled by repressed homosexuality. As Milk grows in stature, assembling a statewide coalition against Prop. 6, enlisting former governor Ronald Reagan and President Jimmy Carter, challenging the proposition’s local sponsor, State Senator John Briggs, to a series of debates, White goes increasingly nuts — as does Jack and indeed San Francisco. White’s lethal freak-out came 10 days after the S.F.-based People’s Temple imploded in Guyana.

The quintessential 21st-century Gus Van Sant movie has been a boldly experimental death trip. Elephant and Paranoid Park both fractured chronology, Gerry and Last Days distended duration but all revolved around young protagonists whose mortality was never less than self-evident. Milk too has a doomed protagonist, but what’s experimental here is Van Sant’s faith in the old-fashioned vérités: Content trumps form as communal solitary redeems individual sacrifice.

Rob Epstein and Richard Schmiechen’s groundbreaking 1984 documentary, The Times of Harvey Milk, spent a third of its length on White’s murder trial, including powerful footage of the flaming riots that greeted White’s conviction on a lesser charge of manslaughter. Van Sant prefers to show a community together. He doesn’t avert his gaze from Milk’s death (foreshadowed by the finale of Tosca, as well as a personal tragedy passed over by the Epstein-Schmiechen documentary), but he wraps it in a comforter of last-day reconciliations, romantic flashbacks and ethereal patriotic music.

Corny as it is, Van Sant’s ending still packs a wallop. Milk is so immediate that it’s impossible to separate the movie’s moment from this one. The 1978 victory over Prop. 6 merges with the current struggle against California’s Proposition 8, overturning the state Supreme Court’s ruling on same-sex marriage. A charismatic leader has yet to emerge but there is . . .Milk, and its wholehearted devotion to the principle of equal protection under the law. (Sound bites from the filmed demonstrations are near-identical to those culled from those held two weekends ago.)

Van Sant and Black position Milk as both gutsy civil rights leader and creative community organizer — not to mention a precedent-shattering politician who, it’s often reiterated, presented himself as a Messenger of Hope. And also Change: “A homosexual with power, that’s scary,” Milk jokes by way of alerting the viewer that he not only anticipated but understood his assassin’s motives. Milk is now. The ecstatic reception accorded Wall-E’s visionary tikkun (and the president-elect’s strategic nonsupport for same-sex marriage) notwithstanding, it’s the first openly Obama-iste movie.

Here’s hoping that Milk and Penn’s Milk do as well in our annual fake election. When The Times of Harvey Milk won its Oscar for Best Documentary, presenter Kathleen Turner described it as “a film about American values in conflict.” This time, the Academy won’t have to be as discreet.

MILK | Directed by GUS VAN SANT | Written by DUSTIN LANCE BLACK | Produced by DAN JINKS and BRUCE COHEN | Released by Focus Features | AMC Broadway, ArcLight Hollywood, ArcLight Sherman Oaks, The Grove, The Landmark

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