After a six-year hiatus, Gus Van Sant returns to feature filmmaking with “Dead Man’s Wire.”

In between, he worked on a TV show “(Feud: Capote vs. the Swans”) and made a few videos for Gucci. Van Sant credits producer Cassian Elwes with stopping him at Soho House in Hollywood to discuss a screenplay.

“Dead Man’s Wire” was based on the story of Tony Kiritsis, the man who broke into the office of Richard Hall, the president of a mortgage company, and took him hostage. What followed was a 63-hour standoff with the police, during which he wired the muzzle of a 12-gauge sawed-off shotgun to the back of the broker’s head. The event became a media sensation as viewers tuned in to watch whether Kiritsis would pull the trigger and how police would handle the situation.

Van Sant wasn’t just drawn to Austin Kolodney’s screenplay; he was attracted to the character. “He was a rebel and an antihero and a man who did a lot of talking,” Van Sant said of Kiritsis. The filmmaker joined *Variety’s *Jazz Tangcay at the Sun Valley Film Festival‘s Coffee Talks for a career retrospective.

Van Sant said yes in September, and Elwes wanted to start shooting on Nov. 1. He started to think about casting, and Bill Skarsgard came to mind: “I thought of Bill, who’s a little younger, and his ability to sort of play very different characters from film to film and wanted to see whether he could morph into this character.” If Skarsgard was his perfect Tony, then “Stranger Things” actor Dacre Montgomery could play Richard.

Van Sant shot the film over 20 days, but rather than recreate some of the news footage of the stakeout, he turned to archival footage shot by both local and national news outlets. “There was a lot of filming going on, with not much happening, but there were reporters commenting on the situation, so we were able to use that.”

The outsider, marginalized character is someone Van Sant has been drawn to over the years, which made Kiritsis the perfect character to add to his body of work.

“Dead Man’s Wire” is not much different from Van Sant’s “Drugstore Cowboy” with both characters at the center of the narrative pushed to extreme actions due to societal and economic circumstances. The director also has an eye for spotting talent early on. Matt Damon and Matt Dillon are just some of the faces who stood out for him.

In “Drugstore Cowboy,” about an ex-con and a group of friends who become drug addicts who turn to robbery to keep their habits going, Van Sant revealed he had cast Tom Waits in the film, but when he presented it to the film’s financiers, it wasn’t well received. “They said, ‘We like Tom, but we’re not really that excited because we have him in another film.” Van Sant continued, “They were thinking somebody a notch higher in their estimation of like box office, and Matt Dillon was on the list. But it started with like Jack Nicholson, of course, Sean Penn was there, and Matt was the third one.”

Dillon eventually got the part.

The filmmaker also talked about “Milk,” his 2008 feature starring Sean Penn as Harvey Milk, the civil rights leader who became the first openly gay elected official.

It took 18 years to make, with various filmmakers, including Oliver Stone and producers such as Neil Meron, attached over the years.

“Robin Williams was going to play Harvey,” Van Sant said. At the time it was under Warner Bros and had a budget of $40 million. “Back then, it was a large amount of money. In the script, Harvey kissed his boyfriend on page 70.” He added that the story differed. “It was [more] about the assassination, Dan White and the Twinkie defense, than it was really about the gay community.”

Van Sant had other plans; he wanted to pull the story more into the gay community and focus on Milk’s activism. “Robin was still involved. We were editing ‘Cowgirls Get the Blues’ in San Francisco and meeting the people of the Castro and the original people in the story.”

But he got tossed off the project. Over the years, other directors got attached to making the movie, and Lance Black eventually ended up writing the screenplay with Bryan Singer attached as the film’s director. “He just happened to fashion his own original screenplay about Harvey Milk using the real characters, interviewing the real characters, and piecing together the story, which he brought to me. And then I thought, oh, great, it’s still alive.” He continued, “One of the amazing things that he did was he took the Dan White trial, which was always one of the most curious things, that he got five years, claiming that he was delusional because it eating too much junk food. So it was known as the Twinkie defense. And the actual trial itself was such a spectacle that having it gone from the screenplay let Harvey’s story live anew. So, we did that.”

Van Sant also talked about eventually working with Williams on “Good Will Hunting” and ad-libbing with Matt Damon. There were long scenes lasting five minutes.

“It was interesting how they could go off and then come back. Matt also was able to keep up.” Van Sant shared that, at times, Robin would play Janet Reno and Damon would imitate Baby Huey. “We would do whole takes with that, which was hilarious.”

However, Van Sant revealed that they never rolled on it. “We could have had a whole film of that,” he said.

Watch the video above.