[Published at the San Francisco Chronicle] Since the beginning of his career, Tiller Russell has had an almost voyeuristic fascination with the underworld — where both cops and criminals are denizens of the morally gray area.

The director’s latest, the Netflix docuseries “Night Stalker: The Hunt for a Serial Killer” and the upcoming feature film “Silk Road,” both visit San Francisco, marking a return to the region that helped pave Russell’s niche path. His films and TV shows represent different degrees of criminality, mildly informed by his days working as a crime reporter at the Berkeley Voice in the ’90s.

“I wasn’t with serial killers or heavy cartel players,” Russell told The Chronicle by phone from his New Mexico home. “But it was a taste of the ability to plunge into the world, connect with real people, pull stories out of them and then bring them to a broader audience.”

The Berkeley Voice’s press pass ultimately served as Russell’s golden ticket into the film industry. Specifically, a fateful dinner with documentarian Errol Morris at a press tour in 1997.

“At the end of the evening,” Russell recalled, “he put his hand on my shoulder, and he said, ‘You’re either going to spend the rest of your life writing about people like me, or you’re going to go try your hand at filmmaking.’ And I literally quit my job at the paper because of that evening with him.”

“Silk Road,” featuring sweeping views of North Beach, Pacific Heights, the Marina District, the Financial District and Pier 39, stars Jason Clarke (in his fourth role in a Bay Area-set film after 2018’s “Winchester,” 2015’s “Terminator Genisys,” and 2014’s “Dawn of the Planet of the Apes”) as disgraced DEA agent Rick Bowden, who obsessively pursues the eponymous dark net marketplace’s architect, Ross Ulbricht (Nick Robinson).

“I remember, on the first day of being on set, sitting there next to” Clarke, Russell said. “I just felt like, ‘God, this is a thoroughbred racehorse.’ ”

“I’ve been a fan of Tiller’s, even before we worked together,” Clarke told The Chronicle by phone from the location of his upcoming film “Black Site,” in Brisbane, Australia. “And in my world, he’s a bit of a cult man from his documentaries. He’s someone that’s prepared to get on the plane, go down to some jail in Israel and try to find this prisoner who’s got this story to sell.”

Both an homage to slick ’90s crime thrillers and a deep dive into amorality in the tech world, “Silk Road” continues Russell’s fixation on crime and moral ambiguity. In the film, Bowden goes down a grisly rabbit hole in his pursuit of redemption, while Ulbricht evades the law with gleeful ignorance. However, ultimately, they both end up in the same uniform: prison garb.

Crime “explores the extremes of human experience, and people want to know what it’s like on the other side, once you cross a line and peek into the darkness,” Russell said.

“There always will be a moral gray area,” Clarke said. “It’s going to cause a lot of political issues but also makes for great narrative storytelling. The temptation is there for all of us. It’s one of those cliches, that Nietzsche quote of, ‘If you’re chasing monsters, be wary of becoming one.’ ”

If Russell’s approach to covering crime borders on detached altruism, Clarke’s approach to his crime-adjacent roles reflects an empathetic misanthropy.

“There was just this explosive volatility to him,” Russell said of his lead. “It’s like, ‘Is he going to reach out and grab somebody and plant a kiss on them, or is he going to smash them over the head with the butt of his gun?’ You couldn’t tell with him.”

“(My acting philosophy has) evolved as I’ve gotten older,” Clarke said. “One of my basics is nothing replaces hard work. … you get your love and your discipline and your craft from hard work.”

Although Clarke wasn’t physically present during the movie’s San Francisco scenes, the city has a way of successfully beckoning the film industry to re-enter its golden gates.

“There’s nothing like going to that bridge and seeing it,” Clarke fondly recalled. “As an Australian, you’re just like, ‘This is America, man. This is the size and the scope and the power of this country.’ And, essentially, that’s what also the film is about — that great history and legacy of American ingenuity.”

For Russell, San Francisco’s draw is more personal: “To this day, I have that homecoming feeling whenever I’m in the Bay Area.”

“Silk Road” (R) in select theaters and streaming on video on demand starting Friday, Feb. 19. Available on Blu-ray and DVD on Tuesday, Feb. 23.