If I’m being totally honest, it takes me a few minutes to shake the fact that I’m sitting across the table from Bill S. Preston as I unspool mic wires in the kitchen of some stranger’s Tribeca apartment. But if there’s stigma attached to having starred in a number of iconic films at a young age, Alex Winter shed it years ago. The career of the self-proclaimed “showbiz lifer” has been a fascinating one to watch over the years, as he transitioned from child/teen star to respected filmmaker, first through the uniquely absurdist comedic visions of his MTV sketch series Idiotbox and the Troma-esque feature Freaked to award-winning features like 2012’s Downloaded, a documentary detailing the rise and fall of Napster soundtracked by former RiYL guest, DJ Spooky. I caught up with Winter as he was in town filming the culmination of the followup, Deep Web, capturing the trial of Silk Road founder Ross William Ulbricht, which concluded three days before our conversation. Though the director was shockingly at ease despite having a number of interviews to conduct just over a month before the film’s premier. That film, which premiered this week at SXSW in Austin, complete with narration by once and future fellow Wyld Stallyn, Keanu Reaves, was, perhaps unsurprisingly, the focus of our conversation, from its birth as a Kickstarter campaign to the relationships he formed with Ulbricht’s family during shooting. Even still, it’s a wide ranging conversation from an accomplished director with no concerns about rehashing old gigs. And hell, when the conversation turns to a third Bill and Ted film, I’m not going to be the one to change the subject.

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