I was 18 the first time I saw Milk, watching in bed with an older guy I had no business dating after recently coming out in my Mississippi hometown.
When Sean Penn took to the podium in one scene as Harvey Milk and addressed “the young people of Jackson, Mississippi,” this little queer world I was just getting to know suddenly started to feel much bigger.
Last November marked 45 years since the assassination of the gay activist and politician, as well as the 15th anniversary of Gus Van Sant's Oscar-winning biopic. He told me about the “very casual” way he first became attached to the project a full 17 years before its 2008 release. The original attempt starred Robin Williams before multiple other stars and directors made their way into the mix.
Sometime around the critical success of his 1991 film My Own Private Idaho, Gus was passing through San Francisco. That's where he had dinner with Rob Epstein, who directed Milk’s 1984 documentary source material, The Times of Harvey Milk.
"He said that Oliver Stone was looking for somebody to take over because he had been working for however long on a Harvey Milk biopic," recalls Gus. "And so I was in LA, and by chance, I met with one of [Stone's] old producers — not anyone that was doing Milk, but a different producer — and I mentioned being interested in the story."
He continued, "It was very casual. And then all of a sudden, because Oliver thought I was right for it, I was having meetings with him and Robin Williams, who was going to play Harvey. We met up a couple times."
Although it's interesting to imagine what Gus could have done with the $40 million budget from Warner Bros. and the late Williams' portrayal of Milk, that version of the movie would have featured a watered-down approach to sexuality, one area where the director is known to be unapologetic.
"I think it was mostly just the way in that era in 1991 and 1992. There was a new script that I was working on, and it was sort of like there was a resistance to show the sexuality of the characters," he explains. "Which it was such a sexual gathering. And it was like Harvey kissed his boyfriend on page 70, and that was about it. I was like, 'No, no. Sex is their reason for coming together.'"
Gus adds, "But I didn't think the script was really getting very far. And our script also wasn't like a sex fest or anything like that in the end."
The filmmaker recalled taking another crack at the script for Warner Bros. in 1995, around the time he made the black comedy To Die For with Nicole Kidman and a young Joaquin Phoenix.
Two years later, amid his first Oscar nomination for directing Good Will Hunting, Gus attempted yet another script with eventual star Penn attached before the project ended up on the back burner again.
"I think it was still kicking around every year, that particular project," says Gus. "Every year was a different gay director."
It was nearly a decade later when Cleve Jones — LGBTQ+ activist, founder of the NAMES Project AIDS Memorial Quilt and friend of Milk (portrayed by Emile Hirsch in the movie) — introduced Gus to Dustin Lance Black, who was developing a script. They teamed up as Bryan Singer's dueling biopic The Mayor of Castro Street stalled amid the 2007-2008 WGA strike.
Gus says Black was the "final piece" in getting the movie made with Focus Features. "He basically just wrote it outside of the book because they weren't going for it. And so he created his own script," he says of Black, who won an Oscar for the screenplay. (Gus was also nominated for Best Director.)
With Penn starring as Milk, it was off to San Francisco, where they recreated the thriving gay scene of the Castro District in the '70s. Luckily, the crew had "so much material and photographs" to work with. "Everyone had scrapbooks," says Gus.
"It wasn't difficult. It also wasn't that far away, the late '70s. Well, I guess it was pretty far away, 30 years," he adds with a laugh. "But still today, I mean except for the condos, it's pretty close."
Not only was the production able to film in the actual building that previously housed Milk's small business, Castro Camera, as well as San Francisco City Hall, where he served on the city's Board of Supervisors, but they were also met by some of the same neighbors Milk encountered in the '70s.
"It was really nice to be able to have been in the original camera shop because the neighbors were some of the same neighbors," says Van Sant. "And there was a guy who had a flower shop across the street who was very antagonistic to Harvey and also us. There were others who were Harvey's allies in the neighborhood."
One visit hit a little too close to home as some crew members recounted a possible spiritual encounter that took place while filming a scene in the crowded storefront where Milk's Castro Camera and campaign headquarters once operated.
"Even though I was watching the scene, somebody said, 'That was weird that that person came up from outside and just sat down next to Joe Cross,' who was playing one of the characters," he recalls. "And I was like, 'There was a guy? I didn't see it.'"
Gus continues, "And they said, 'Yeah, some strange person walked in and sat down.' And I said, 'What did he look like?' And they were describing Harvey, basically. I was like, 'Oh my God.' I might not have seen it but maybe it was a ghost or something. I was watching the scene, but there were like nine people in the room and I didn't see it."
With or without the supernatural guidance, Penn "was pretty much in his own interpretation" of Milk, who was assassinated along with Mayor George Moscone (played by Victor Garber) by former supervisor Dan White (Josh Brolin) on Nov. 27, 1978.
"He had a lot of materials to relate to and to read and to watch, and he kind of channeled him," says Gus of Penn's Oscar-winning performance. "And it was great."
Although his involvement was largely instrumental in bringing the film to fruition during a polarizing era for representation, Penn's Oscar win sparked some criticism over Hollywood's continued casting and praise of cis-het actors in LGBTQ roles.
"I think it's a cool thing to be able to have a character that is politically, and/or in this case, his sexuality matching the character," says Gus, adding: "I see the value in finding somebody to represent a character who is really living the life."
He continues, "But I kind of come from a time and place where they're not really documentaries. They're like pantomimes. So, you know, I'm all for gay people playing straight characters or straight people playing gay characters, or women playing men, or men playing women."
Thirty years after Milk's death, the movie debuted amid another big fight for the LGBTQ+ community. "The gay marriage fight was the thing that was happening at that time," says Gus, referencing California's Prop 8.
He notes that Black was "involved in a lot of the local politics," fighting the proposed ban on same-sex marriage (although Prop 8 passed in November 2008, it was later ruled unconstitutional in 2010). Gus said, "It was kind of great" seeing the community come together at the time.
Gus finds it "scary" that the politics of today don't seem far from Milk's era, with Don't Say Gay bills targeting LGBTQ+ teachers and major beer brands caught in a culture war. Meanwhile, Prop 8 was officially repealed last summer as marriage equality is threatened once again.
"It's crazy," he adds. "I mean, it's almost like everything's reverting back to not even the '50s, but more like Nazi Germany and the '40s."
As Harvey Milk's friends and supporters gathered in November to remember him and Mayor Moscone 45 years after their deaths, the movie continues to preserve his legacy.
"It was kind of hard because he was so beloved in his community that we were trying to be as respectful as possible," says Gus.
Milk is now available to rent and own on Amazon Prime and Apple TV.