Legendary photographer Annie Leibovitz took a series of photographs of some of this year’s actor/director pairings for the latest Vanity Fair.  You can see why she’s legendary, because she’s managed to TAKE PICTURES of CELEBRITIES in front of a GREY WALL.  How does she do it?  This kind of genius doesn’t come naturally. She may have sold her soul to the devil.  Or bathed in the blood of Christian babies. In fact, I think I read that somewhere.

^{Penn gets his first eyeful of James Franco’s prosthesis}

After the jump, I’ve got the first trailer for Milk, which premiered last night. Directed by Gus Van Sant, Sean Penn plays Harvey Milk, San Francisco’s first openly gay city councilman. It looks like they made this from the perspective that Milk is some kind of courageous crusader for the rights of the little guy. I don’t want to spoil the movie, but Milk later gets murdered in cold blood by Dan White (Josh Brolin), who uses the “Twinkie defense” to beat a murder rap and ends up serving only five years in prison. I’m not sure how they’ll paint that as a heartwarming triumph over adversity. Unless there’s, like, a lot of prison rape. They say prison rape is the great equalizer.

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EW has the first production still from Milk, the Gus Van Sant biopic about assassinated openly gay San Francisco city official Harvey Milk. Ha, more like Gus Van Can’t–make-a-decent-movie-lately, am I right, guys?  High Five?  Anyone?

Explains producer Dan Jinks (American Beauty). "[Sean] is playing a guy who’s not at all like him, way beyond the sexuality of the character. Harvey was this guy who wanted everybody to love him, and he loved everybody else. Sean just completely became that guy. It’s a real transformation.”

Jinks went on to say that Penn was aided in his transformation by tiny little champagne flutes that make everyone who holds them look super queer.  "We originally wanted other guys’ cocks, but the champagne flutes seemed subtler," he said.

This is the trailer for Paranoid Park, directed by Gus Van Sant – director of better-than-mediocre studio movies (Finding Forrester, Good Will Hunting) and annoyingly pretentious indie flicks (Elephant, Last Days).

It’s about "a 16-year-old skateboarder accidentally killls a security guard at a skate park."

It looks pretty unrealistic, considering it’s set in Portland and doesn’t seem to have any lesbians or homeless people in it.  I also probably would’ve cast a kid who could actually read as the main character, but that’s just me. (opens March 7th) 

Watch it in HD

Josh Brolin, Emile Hirsch and James Franco are all in final negotiations to star alongside old Weisbecker chum Sean Penn in Gus Van Sant’s Harvey Milk biopic, Milk. 

Harvey Milk was the openly gay San Francisco city supervisor who was assassinated in 1978 by political rival Dan White.  

Brolin will play the rival, Dan White, who shot both Milk and San Francisco Mayor George Moscone to death at City Hall. Hirsch has been cast as Milk’s political ally Cleve Jones, a gay-rights activist who went on to found the NAMES Project AIDS Memorial Quilt. Franco will play Scott Smith, Milk’s lover and campaign manager. [Yahoo/Hollywood Reporter]

It’s a little sad because Bryan Singer and Chris McQuarrie, the team behind The Usual Suspects have also been attached to a Milk biopic, and for a lot longer than Penn and Van Sant, but all the news of late has been about the Van Sant version.

But what a year for Josh Brolin, huh?  The guy’s already appeared in Grindhouse, No Country for Old Men (when he was cast by accident), In the Valley of Elah, and American Gangster. Good for him – he’s a good actor, and  he probably has some good Karma built up from having Barbra Streisand for a Stepmother.  That must be weird.  I see my stepmom sometimes.  She’s a Bangladeshi boy who came to my house in a wooden crate.  I beg her to read me bedtime stories, but mostly she just whines about being fed. Moms are funny like that.