DEEP WEB Review: Alex Winter’s Documentary Takes Viewers Down The Silk Road

     May 30, 2015

deep-web-review

Here’s what you need to know to understand where Alex Winter’s documentary Deep Web begins. When you browse the internet and use search engines to find content, you’re engaging in the “surface web.” Whenever you put in a password to log in to a protected website or webpage (your email client, online banking, protected corporate or government sites), you are accessing the “dark web.” If you are going totally off the grid to find sites that are completely anonymous except through the use of special software, then you are on the “deep web.”

The most famous example of the deep web is The Silk Road, an online marketplace for drugs and other illegal items that launched in 2011. Its name became part of the national conversation after a raid by the FBI appeared to have uncovered its leader — an administrator going by the name “Dread Pirate Roberts” (from The Princess Bride) — 29-year-old named Ross Ulbricht.

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Image via Epix

That wasn’t the end of The Silk Road, nor of Ulbricht’s odyssey through the legal system. Winter’s documentary takes a linear approach in explaining the deep web, Tor, onion sites, Bitcoin, and how they all relate to The Silk Road and Ulbricht’s bid for freedom.


Deep Web began as a Kickstarter campaign, and an extension of sorts to Winter’s documentary short Downloaded, which was about the rise and fall of Napster. For Deep Web, Winter brought along his Bill and Ted’s Excellent Adventure co-star Keanu Reeves to narrate, adding a little celebrity interest to the project.

But Deep Web really doesn’t need it — it stands on its own as a fascinating look at the story of The Silk Road. Wired writer Andy Greenberg, who had at one point communicated with the Dread Pirate Roberts (who may or may not have been Ulbricht at the time), wrote a series of excellent articles about The Silk Road and Ulbricht’s case, and also acts as a consulting producer for the documentary as well as one of its main pundits. Greenberg is both thorough and thoughtful in discussing the information, and he (like the documentary’s overall tone) is more interested in the story itself than any revelation of absolute truth.

Deep Web orients viewers through graphics and narration to a world many viewers may not be familiar with, but its not so broadly accessible that there aren’t things that even those who have diligently followed The Silk Road case can’t learn from its presentation and arguments. One of the most interesting things Deep Web broaches is how search the seizure laws affect the internet, and whether or not Ulbricht’s case (which is currently in sentencing stages — the documentary is updated through the first of May) might have all fallen down if the FBI had been forced to admit how they were able to access the Silk Road server in the first place. (Greenberg suggests the most likely scenario is that a foreign server was hacked without a warrant).

Deep Web balances the arguments for and against the politics and ethics of these complicated issues for awhile, interviewing figures from both sides of the aisle (many of whom acknowledge there’s no absolute line that can be drawn). Still, there’s definitely a bias that begins to develop as the documentary continues. Winter also is able to interview Ulbricht’s greatly supportive parents, as well as his friends and others who want to help paint a truer portrait of the man being accused of masterminding the entire site. Ulbricht himself, who is facing life in prison, released a statement that focused on hope.

deep-web-andy-greenbergBut Winter also lets Ulbricht speak through personal video and photographs from his earlier life, growing up as an only child in a middle-class family. He also uses screenshots, text on the screen, and other graphics to help viewers feel like we are hacking into these sites and seeing these interactions ourselves. Further, Winter is able to get some Silk Road vendors to speak (with disguised voices), and spends a lot of time examining the kind of community that the site fostered, one whose main desire was “to do no harm.”


Whether that really was true or if it continues to be true (as splinter sites continue to pop up, those which may not carry that same philosophy) is a question pondered, but that is impossible to answer. In fact, there’s really almost too much for the documentary to handle in a mere two hours. But despite a few tangential detours, Winters mostly keeps the material in hand while also allowing Deep Web to feel like a launching point more than a complete story. That’s because there’s still so much yet to come, and it may never be over. Greenberg, quoting a cryptologist, sums it all up by saying, “in this cat and mouse game, the mice will win in the end, but the cats will be well fed.”

Many great articles have been written about The Silk Road and Ulbricht’s trial, but Winter is the first to bring it all together visually in a highly engaging story that puts faces and personalities to what can otherwise seem like vague and cold concepts. Deep Web has proved itself as both a necessary and fascinating watch. At its best, a documentary should absorb the viewer into its world, creating a compelling statement, and possibly even encouraging a desire to know and learn more. Deep Web does all of these things, and subtly nudges viewers to consider how the future of privacy on the internet affects us all.

Rating: A-

Deep Web premieres Sunday, May 31st at 8 p.m. on Epix.

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Image via Epix


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