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The passing of Proposition 8 hangs over Gus Van Sant's biopic Milk, which follows the life and death of Harvey Milk, the first openly gay man elected to public office. His legacy as San Francisco city supervisor and martyrdom at the hands of fellow Board Of Supervisors member Dan White are watershed moments in the ongoing battle for gay rights in America. Prop 8 gives the film immediacy, but more importantly, it lends some much-needed (and surprisingly heartening) perspective on how far the movement has come, and how far it has yet to go. But a measuring stick does not make a movie, and Milk, for all its admirable qualities, doesn't transcend the problems inherent to biopics; it loses some of its power to the same lumpy conventionality that scotches most cinematic attempts at portraiture.


After his ham job as a Huey Long-like demagogue helped sink 2006's abysmal All The King's Men, Sean Penn redeems himself as Milk, perhaps because he's committed himself to something deeper and more empathetic than mere imitation. His strong performance provides crucial ballast to the winding narrative of Milk's life, which hits a lot of dead ends and detours before his rise to political and cultural prominence. Starting in 1972, the film follows Milk as he moves with his boyfriend (James Franco) from New York to San Francisco, where he opens a camera shop on Castro Street. Milk watches the neighborhood as it transforms from a working-class block to the country's most famous gay enclave, and his political fortune changes along with it. After losing three times in various campaigns for local office, he takes advantage of redistricting and wins a spot on the Board Of Supervisors, where he serves for a year before White (Josh Brolin) assassinates him and mayor George Moscone.

Once Milk finally enjoys some political leverage, the film gets a lift from his most famous legislative fight, a failed bid by California State Senator John Briggs (with an assist by touring bigot Anita Bryant) to ban gays from teaching in public schools. Until then, Van Sant excels more at defining the evolving atmosphere of Castro Street and America in the '70s than the individuals in Milk's orbit, particularly lovers played by Franco and Diego Luna, and a key young operative played by Emile Hirsch. Remarkably, the film's most compelling, conflicted figure is Brolin's White, whose frustrations and mounting psychosis over the changing times is somehow more accessible than any of Milk's legions of followers. After an artistic resurgence behind true independents like Gerry, Elephant, Last Days, and Paranoid Park, it's a little disappointing to see Van Sant dial back into mainstream respectability. Had he evoked Harvey Milk's life with the poetry that he did Kurt Cobain's, Milk might have been something special.