Finding Compelling Characters

Actor-turned-director Alex Winter talks the tech documentary rabbit hole and his forthcoming project, on Frank Zappa

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Alex Winter may be best known for the big screen “excellent adventures” he and Keanu Reeves got themselves caught up in as the time-traveling metalhead duo of Bill S. Preston, Esquire, and Ted Logan.

Acting in Bill & Ted-style romps, though, just isn’t the kind of thing that interests Winter anymore. And since putting acting behind him in the ’90s, Winter has re-emerged in recent years as a documentary filmmaker. He’s drawn to cerebral projects with big, important themes at their core, projects that let him tell the stories of misunderstood and often difficult men.

It’s a career turn that might seem unexpected, but for the fact Winter always preferred working behind the camera to standing in front of it. Fresh out of film school at New York University, for example, he happily wrote and directed commercials, and he’s continued to do that kind of thing—helming TV spots and a variety of episodic shows—throughout his career.

At the moment, he’s busy writing an hour-long drama for the Hulu streaming service—the details of which he’s keeping under wraps for now—in addition to starting work on his next documentary. With a working title of, simply, Zappa, it will examine the life of the idiosyncratic, outspoken artist and musician Frank Zappa.

Planned for release in late 2017, at the earliest, the film will follow earlier Winter docs in presenting the stories of figures like Napster co-creator Shawn Fanning and Silk Road mastermind Ross Ulbricht.

“I’m always looking for a theme,” says Winter, whose previous documentary, Deep Web, headed to iTunes and other digital outlets September 1.

The film gives viewers a look at the seedy underground of cyberspace, the hidden corners where Google’s engine doesn’t crawl and where privacy advocates—and criminals—roam free. Telling the deep web story takes audiences everywhere from the rise of Bitcoin to the morally fraught landscape of the Silk Road black market.

In an interview with Paste, Winter explains that his hunt for new stories tends to start with interest in a theme and a central character or “constellation of characters”—as with his 2013 documentary, Downloaded, which focused on Napster and its co-founder, Fanning.

“The Napster case was about a naive, brilliant computer genius, Shawn Fanning, and the constellation of characters around him making Napster happen,” Winter says. “But I was mostly interested in Shawn—as a moralist, humanist, someone who wanted to bring people together online, yet he created something so many people hated and vilified.

“And then with Ross Ulbricht, it doesn’t get more paradoxical than that. We don’t know anything about him. There’s this duality between whether he was the [Silk Road creator] Dread Pirate Roberts or this extremely pacifistic, community-oriented person who wanted to use technology to create a large-scale, anonymous community and yet is facing the rest of his life in jail without parole. That was so compelling.”

With two projects that took him down the tech rabbit hole, Winter looked for something different in considering his next film. He and producing partner Glen Zipper began discussing potential subjects.

Frank Zappa—a boundary-breaking musician who died in 1993—eventually rose to the surface.

“Everybody has a different impression of who he was,” Winter says. “They think he was a novelty act. That his politics were phenomenal—or asinine. He was just an extremely compelling individual who lived at an extraordinarily challenging time in our history. And he embraced those times and tried to impact those times. He was very brave about it. He didn’t just follow a particular line. He was his own person.

“Those are the types of characters I’m interested in. And they’re not easy. They’re not always easy for people to swallow.”

The project not only has the support of the Zappa Family Trust, the late artist’s estate has also given Winter access to what he calls “the vault”—an entire floor’s worth of space filled with Zappa-themed media Winter says no one has seen before.

The trove of material—interviews, family footage, music and other art—is extensive, and the task of sifting through it formidable enough that Winter says the process will take about a year.

“I’ve always loved documentaries,” he says. “I think they’re great cinema and have always held them in very high esteem.”

Winter explains how he “fell sideways” into his current run of documentary projects. He first pursued Downloaded because he felt the world didn’t understand the entirety of the Napster story. With a journalistic eye toward veracity and detail, Winter met with Fanning and got a sign-off from him, after which he went about selling the film to a major Hollywood studio.

Winter intended to direct it as a regular narrative feature about the technology revolution until, as things often do in the studio system, it “stalled out.”

“I wrote seven drafts [of the script],” Winter recalls. Studio executives involved with the project eventually left, and with no one around to champion it, Downloaded sat.

But Winter didn’t want it to languish. “It was too important to me,” he says. The solution: He decided to take the documentary route.

The forthcoming Zappa project represents but the latest in a series of characters Winter wants to examine, stories he wants to tell, and places he wants to use his lens to illuminate. And he shows no signs of slowing down.

It’s too important to him.

Photo by TechCrunch, CC-BY/p>