Penn to star as Harvey Milk

Director Sean Penn listens to a question during the news conference for ''Into the Wild'' at the 32nd Toronto International Film Festival September 9, 2007. Penn is attached to play gay '70s San Franciso politician Harvey Milk, and Matt Damon his assassin in a long-gestating project from director Gus Van Sant.

TORONTO (Hollywood Reporter) - Sean Penn is attached to play gay '70s San Franciso politician Harvey Milk, and Matt Damon his assassin in a long-gestating project from director Gus Van Sant.

Once a distribution deal is finalized, Van Sant hopes to begin production on the as-yet-untitled feature in San Francisco as early as December. The uncertain start date may affect Damon's participation as Milk's killer, Dan White.

It's the latest chapter in a long-running race to film the biopic of the first openly gay prominent elected official, which has pitted Van Sant's project against another from fellow openly gay director Bryan Singer.

Producers Craig Zadan and Neil Meron ("Hairspray") have attempted to produce a big-screen version of Randy Shilts' 1982 bio "The Mayor of Castro Street" for more than 15 years. Warner Bros. Pictures attached Singer to the project two years ago.

This summer the studio's art-house arm, Warner Independent Pictures, brought in Singer's "Usual Suspects" scribe Chris McQuarrie to write a new draft of the script. But McQuarrie is now in Germany with Singer working on the Tom Cruise drama "Valkyrie" and also working on the "Castro" script, making an immediate production start less likely to happen before Singer starts his "Superman" sequel commitment.

In a coincidental twist, Van Sant once wrote a draft of the "Castro" project and was set to direct his adaptation for Warners. The script for his film was written by Dustin Lance Black ("Big Love"). Producer Michael London and his Groundswell Prods. are financing the film, set to be produced by "American Beauty" producers Bruce Cohen and Dan Jinks.

Penn has never portrayed an openly gay character onscreen, but he did play the sexually ambiguous Olivia Newton-John impersonator "Groovin' Larry" in a section of Trent Harris' 2001 cult hit "Beaver Trilogy." Penn's video short was shot in 1981, then combined with Harris' 1979 documentary short on the amateur performer and his 1985 short narrative version "The Orkly Kid," starring Crispin Glover as Larry, to create "Beaver."

Damon would play White, who shot San Francisco city supervisor Milk and Mayor George Moscone in 1978. After serving five years of a seven-year sentence, White committed suicide in 1985.

Reuters/Hollywood Reporter