Many actors have survived the intensity of Hollywood fame with second careers, but few have followed a trajectory as fascinating as Alex Winter’s. After skyrocketing to stardom as Bill S. Preston opposite Keanu Reeves in 1989’s “Bill & Ted’s Excellent Adventure” and its 1991 sequel, Winter grew disillusioned with the movie business. He grew sick of the pressures of the spotlight and, as he would reveal decades later, still contended with trauma of sexual assault experienced in his childhood. But Winter escaped through twin obsessions that would form his career: filmmaking and the internet.
Nearly 25 years after Winter gave up on professional acting, he’s enjoying a new life as a serious documentarian, with movies that untangle some of the thorniest questions surrounding modern technology. Following the Napster-focused “Downloaded” and the dark web portrait “Deep Web,” Winter has completed two new documentaries that reveal the intensity of his obsessions.
In “Trust Machine: The Story of Blockchain,” Winter demystifies the paradigm shifts of digital currency. “The Panama Papers,” which airs on Epix this month, explores the coordinated efforts by 400 journalists to expose tax fraud by combing through millions of leaked documents. Like his cohort Laura Poitras, Winter is charting a path toward clarifying rapid technological changes with a series of documentaries loaded with breathless observations about an unpredictable new frontier.
Popular on IndieWire
“Technical stuff is largely misunderstood,” Winter said in an interview, as his new works began their festival rounds. “This world is filled with really interesting people. Some of them are legitimate, and some of them are really batshit crazy, and I was really interested in trying to put my arms around all of that.”
Winter’s non-fiction oeuvre tracks a range of intense personalities enmeshed in the uncharted and often dangerous possibilities of the digital landscape, from Napster founder Sean Fanning to Ross Ulbricht, who operated the darknet operation Silk Road until he was arrested and sentenced to life imprisonment on a range of charges. Winter approaches these subjects with clear-eyed, scholarly precision. “I want to make movies about people in this crazy, compelling, polarizing moment we’re in,” Winter said.
His relationship to the internet began in the primal days of Usenet forums in the late ’80s, where he discovered that the the anonymity of online communication provided a welcome relief from celebrity. “It was kind of a decentralized global community,” he said. “I found it very, very liberating. I really found solace on internet.” He began to explore some of the anger and frustration over his assault. “Some of the stuff from my childhood was beginning to catch up to me,” said Winter, who came forward earlier this year as the survivor of sexual abuse as a child actor in the early ’70s, but declined to identify the perpetrator, who he said was no longer living. “I found this sort of post-trauma community before I started dealing with stuff in therapy in a hard-and-fast way.”
In 1993, Winter directed the surreal cult movie “Freaked” on a shoestring. Then he quit acting, moved to New York, and then London, where he launched a film production company. After his 1999 thriller “Fever,” he reached another crossroads. “I was really happy with it,” Winter said, “it was very little and uncommercial, so no one was going to throw money at me to make the next one.” He developed a series of bigger projects that failed to materialize, including a narrative about Fanning and the early days of Napster for Paramount. He connected with Fanning and developed an instant bond. “He also had a very traumatic, difficult upbringing,” Winter said. “I really related to how he felt under the glaring media spotlight.”
Napster, which was vilified for the legal ramifications of sharing licensed music online, fascinated him. “It was this extraordinary way of connecting, because music is so powerful,” he said. “So that sparked me to telling these type of stories, looking at who the real people are in this space. It’s not to exonerate them, but to look at the full picture.”
The prospects for a Napster movie looked good, until one day, Paramount fired much of its development staff and cleaned its slate. “This script had gone through many iterations for a long time,” Winter said. “I thought at that point, ‘I know everybody. I spent a long time researching the story and writing it as a narrative. Why don’t I try pitching it as a doc?’” He went to VH1 executive Van Toffler and sold “Downloaded” the same day. “After spending 10 years banging my head against the wall, we’re shooting like a week later,” he said. As he interviewed Fanning about his life and his career, Winter said, “I was listening and asking questions. At that moment, I thought, ‘This is so much better than my narrative would’ve been.” That led to a larger truth. “I was hooked by these levels of truth and untruths,” he said. “I was so totally smitten with the process that I didn’t ever want to stop making them.”
Winter hasn’t given up on directing narratives — he recently sold a one-hour pilot to HBO, but “I don’t ever intend to stop making docs,” he said. “It’s the most creatively gratified I’ve ever been.” Meanwhile, he’s reconciling with his past in a more endearing fashion, by reuniting with Reeves for the long-awaited third entry in the “Bill & Ted” franchise entitled “Face the Music.” Reeves, who lent voiceover narration to Winter’s “Deep Web,” has remained a part of Winter’s inner circle over the years.
“Keanu and I are very, very close friends,” Winter said. “So it’s just a friendly, inviting environment. We’re talking all the time regardless, so it all felt like a creative endeavor for a group of friends.” The concept of a third “Bill & Ted,” tracking the time-traveling rock ’n’ roll dudes into midlife crises and fatherhood, had been tossed around for years. “We’ve been pretty philosophical about it, like if we could get it made, great,” he said, “but if it’s not going to get made to our creative specifications, we’re all perfectly happy not doing it.”
He said he was content with a script from co-writers Chris Matheson and Ed Solomon, which Dean Parisot will direct next year. Steven Soderbergh has offered his insight as an executive producer. “The idea is really just to make a sweet, enduring, and legitimately funny movie,” Winter said. “We genuinely believe these are timeless comic characters, not because they’re brilliant or anything, but just in terms of their cartoonish, clownish essence.”
Circling back to his current professional life, Winter compared the prospects of the next “Bill & Ted” movie to “Anvil!”, the documentary about aging heavy metal rockers past their prime and reuniting in middle age. “The affectionate nature of people trying to reunite as a rock band is a great comic conceit,” he said. He has plenty of documentary projects in the pipeline, some of which he’s not ready to talk about, but he’s keen on taking a breather. “I really just need to turn that entire side of my brain off,” he said, “and be the dumbass that Bill is for three months.”
Blockchain-based distribution company SingularDTV is releasing“Trust Machine: The Story of Blockchain,” which is now playing at Cinema Village through November 9. It opens in Los Angeles at the Laemmle Monica Center November 16.