Wylie Writes’ One-On-One with Alex Winter



By: Addison Wylie

Movie goers will recognize Alex Winter as Bill S. Preston, Esq. from the time traveling cult classic Bill & Ted’s Excellent Adventure and its sequel Bill & Ted’s Bogus Journey.  I was one of  those people, but then I was exposed to Winter’s directorial efforts.  Now, I’m someone who instantly recognizes the actor-turn-filmmaker as one of the best documentarians working today.

Downloaded, Winter’s chronicling of the rise and fall of Napster, was sensational.  It utilized its nostalgic connection, but didn’t rely on it.  Its story about wiz kids who brought the music industry to its knees through file sharing was absolutely compelling.  Deep Web trades in nostalgia for facts about an online underbelly used for selling illegal goods.  It was a dark place that sparked loads of controversy and erupted discussions about privacy.  The documentary has a mighty message at the end credits, and a recent real-life sentencing to Deep Web’s main subject only makes the message stronger.

When I got a chance to talk with Alex Winter about Deep Web, I was inclined to pick his brain about his interest towards cyberspace.  However, I couldn’t help but ask the filmmaker about his choice of narrator – his Bill & Ted co-star Keanu Reeves.

Addison Wylie: With Downloaded, your upcoming feature SMOSH: The Movie, and Deep Web, you seem to have a fascination with life that exists online.  Has the digital age always intrigued you?  What about the online world interested you?

Alex Winter: I first got involved with online communities in the 80s; in the pre-web era, through Usenet, the BBS groups, and all of the things that you find in the dark net.  They all existed back then, but on a much smaller level.  There were music communities – sort of pre-Napster. Social communities – pre-Facebook.  There were anonymous and private communities including drug markets back then too.  So, I’ve had an interest in this world for a very long time.  The work I did on the Napster movie helped me form a lot of relationships with people that were instrumental in creating these technologies.  That was my way through that area into making Deep Web.

I guess to answer the second part of your question, as to why it interests me, we live in a very – how shall I put this – dramatic time.  Where there is a shift happening from the industrial age to the technological or digital age, which has a huge impact on human culture, on a moral level, on an ethical level, and on a practical level of how we exist.  It isn’t so much the technology that interests me, its the human implications of these changes that interest me.  That’s why I like focusing on stories that involve complexity, that aren’t black and white.  The Napster story was not a black and white story, and certainly the story of The Silk Road isn’t black and white.


AW: I have to ask you about Keanu Reeves’ involvement with Deep Web.  He’s a very articulate and competent narrator, but were you also going for another cinematic connection between him and the material?

Alex Winter: Keanu is an awesome actor.  Its a funny thing to say he is articulate because I wrote all of his narration [laughs].  That aside, I wanted Keanu to do it because as a performer, he is a really strong actor. He has the ability to captivate, which is by no means easy.  And, he doesn’t do this with every role, but I knew he had the capability of conveying emotions without imposing an editorial voice, which was really imperative with this movie.

The secondary reason – and really, it’s a very distant second – was that I knew that Keanu had a kind of associative connection to this world. Because of Johnny MnemonicThe Matrix, and A Scanner Darkly, he is known in the cyber community. Its not that people see him as Neo – it’s not that superficial. He is genuinely known within the hacker community as someone who has an affinity for that world, and that was important to me.

AW: What’s your next project?

Alex Winter: I’m working on a number of projects. I am working on a documentary at the moment where I can’t disclose the subjects  just yet, but I will be very soon.  I am also working on a documentary, not on the tech space, but it does involve some of the issues that I’m interested in.  Aside from the documentaries, I am working on two hour-long television dramas for cable that are also not unrelated to the issues that I find compelling as well.


Deep Web is now playing at Toronto’s Bloor Hot Docs Cinema.

Click here to read Addison Wylie’s Deep Web review

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