Epix’s New Documentary Explores the Deep Web

Deep Web - Alex Winter and Keanu Reeves

The Deep Web—or, more specifically in this instance, the Dark Web—has been around since the earliest days of the internet, accessible through certain anonymizing networks like Tor; it’s different from the exposed cacophony of the Surface Web, where sites are indexed by search engines and accessible to anyone.

Silk Road popped up on the Dark Web in 2011 as a black market for just about any illegal good or service you could think up, created and run by a user account called “Dread Pirate Roberts” (a Princess Bride reference, of course). At least one of the several people using the DPR account ended up being Ross Ulbricht, a 30-year-old entrepreneur who was arrested while he was logged in to Silk Road as an administrator. Ulbricht admitted to being the creator of Silk Road, and was convicted in February on various counts of drug trafficking and money laundering.

Epix’s new documentary Deep Web digs into the creation and destruction of Silk Road 1.0, and the case built around Ulbricht. (Silk Road 2.0 was also taken down by the feds, but Silk Road 3.0 lives on.) We talked to director Alex Winter (Bill from Bill & Ted’s Excellent Adventure) about the War on Drugs, helping people understand technology, and using buddy Keanu Reeves as a narrator.

This isn’t your first tech-centric doc—you did Downloaded a couple years ago, about Napster and the ushering in of the digital music age. Was this a natural follow-up?

I see the movies as somewhat connected. They’re part of a larger conversation about human stories caught up in the gears of the digital revolution. And looking at the human perspective on that, and the ramifications, and even the casualties of it.

What made you hone in on Ross Ulbricht as the human perspective?

It was the unknowable, in a lot of ways. It was the fact that it really struck at the essence of how difficult it is to wrap our heads around these online personalities. We’re dealing with anonymous communities, with fictitious usernames, with cryptocurrency. I really think that was my impetus, was just exploring the world around this guy, more than exploring the guy. We know nothing about him—that was kind of my point. Exploring the world around him as this extraordinary chain of events goes down.

The doc is airing on May 31, but his sentencing isn’t until May 29—will you be able to get that information in?

Yeah, that’ll be in. We’re just putting a card in at the end. It won’t change anything. The case isn’t changing. It has enormous significance for him and his family, obviously, but in terms of the narrative, there’s nothing occurring at the sentencing that I would need to document, other than what the sentence is. I don’t have a bombshell to drop on anybody.

Silk Road was used for more than just drugs, but that’s what you focus on most heavily.

Frankly, I find that with issues in technology, specificity is really important for any kind of comprehension. I didn’t believe there was any way to explain this entire landscape in a single movie. The best thing you can do for people is to put brackets around a smaller story within this larger story and really focus on it. And actually, the drugs are really significant, and not only because the War on Drugs played a large part in the motivation for the Silk Road and combating it using technology. It’s sort of naively optimistic to come at it that way, but that’s just the way it was. On the other hand, similar to the way music was the driving delivery system for creating larger online communities with Napster, drugs were the delivery system for creating a large-scale anonymous community on the Dark Net.

You have a major from the Baltimore Police talking about how an online marketplace like Silk Road could actually reduce drug-related violence. Was he hard to find?

It wasn’t difficult for one thing to lead to another and find one of the more important front-ends from the law enforcement side, in trying to find ways to reform the drug situation and the drug war. He’s not there to say the Silk Road was good—he’s there to say that these are unpalatable, thorny issues that nobody wants to address, and they need to be addressed.

Ross doesn’t appear on camera—did you get to speak to him at all?

I wasn’t allowed any access at all. It was somewhat to do with the prison system and the severity of the charges that he was not going to be filmed by anybody. And also, I gotta be totally honest with you, it wasn’t something I was pushing for. I didn’t want to become biased. I have compassion for the family, and I think that shows. And I do have compassion for anybody who’s caught in the middle of something this complex.

One would think the Silk Road vendors would shy away from talking to you, but several appear in the film. Were they eager to talk?

They were. Once I really made it clear what I was doing, and got kind of down and dirty with them about my interest in the story, they were open to talking, and there was a level of trust there.

How do you establish that kind of trust?

You know, a lot of back-and-forth. They were only going to talk about certain things. I watched this happen with the Napster community, too, it was very similar: There was a realization that the narrative around the Silk Road was going to get very narrow, and, in their view, misrepresentative of the truth. And I think there was an eagerness to convey the facts of that community as they saw them. You had to be pretty technologically adept to function on Silk Road, especially if you helped build it. So I wasn’t dealing with out-there people—I was dealing with very well-spoken, well-educated people. I didn’t always agree with them, but it was more like talking to computer scientists than drug dealers.

You and Keanu Reeves go way back—was he always your first choice as narrator?

To be honest with you, I wasn’t thinking about narration at all while I was making it. I hate narration in docs very much, so I’d tried to cut it without narration at all, but there was just too much information that people need guidance around. So it became imperative to have narration. And then towards when I was going to show the movie at South by Southwest, I realized, “Well, I better figure this out sooner rather than later.” [Laughs] Keanu had been sort of a consulting producer all along, he’d been present during the process, so it was a fairly easy ask.

Deep Web, Premieres Sunday, May 31, 8/7c, Epix

Deep Web - MGM+

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