Deep Web: The Hunt for Dread Pirate Roberts (2015)

A feature documentary that explores the rise of a new Internet; decentralized, encrypted, dangerous and beyond the law; with particular focus on the FBI capture of the Tor hidden service Silk Road, and the judicial aftermath.

Jess' Review

Ever since stumbling across a podcast discussing the atrocities of the dark web (which may or may not be true let me add), I’ve been fascinated with this hidden world. I find it amazing that there is this whole hidden, online universe that is so vastly inhabited and seemingly unrestrained in its content. And so when I spotted Deep Web: The Hunt for Dread Pirate Roberts tucked away on Amazon Prime, I was intrigued. First feature-length documentary - Sam’s going to love this...

Deep Web documents the search for and ensuing arrest of Dread Pirate Roberts, administrator of notorious drug-dealing enterprise, Silk Road. The film is expansive, leading us on a journey from culmination of the website to, what I personally find, an unsatisfying end. Not entirely on account of the filmmakers, but rather as a result of what seems a flawed judicial system.

Now, I’ll be honest, this was a hard watch for me. Director Alex Winter is constantly feeding you information from the get-go, with a lot of this already being quite specialist, surrounding topics of privacy laws, hacking, cybercrime and philosophy. And that’s even before we’ve hit the trial and face further complexities that relate to our personal views on this matter. Perhaps I’m not the sharpest tool in the shed, but I found myself lost on more than one occasion. And I remain totally divided on how I feel about how Ulbricht’s story ends.

Deep Web is well-made, and clearly constructed with a great deal of attention to detail. There are countless interviewees, all with their own areas of expertise and new slice of information. It becomes overwhelming at times, though I suppose necessary to capture the scope of the topic. Keanu Reeves’ narration helps guide us away from these separate avenues of intrigue, to eventually fixate on the story of one man and his stand-off with government practices. It is a lot to digest, though quick to provoke further discussion even as the credits roll. I admire Winter’s ability to do this, though I cannot help but feel there is a level of bias here.

All in all, Deep Web was as interesting as it was shocking. But my issue is with its delivery. The film felt too intense for me, too long-winded and in its pursuit of interviewing such a range of people, left me feeling a bit bored. Perhaps it would’ve been better suited to a series in nice, bite-size chunks, or more all-encompassing as a book? Regardless, it was thought-provoking and if you’ve got the focus, worth a watch.

5/10

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Sam's Review

Ross Ubricht's life is certainly fascinating. Accused of being Dread Pirate Roberts, the administrator of the Silk Road, an anonymous website that facilitated the selling of drugs, he is painted as a drug Kingpin by the authorities. A stark contrast to the playful man we see in home video clips dotted throughout the documentary.

This couldn't be told properly in an hour and a half, no matter how good the execution. And unfortunately this is not executed well. They waste the beginning of the film, so much so that I fail to recall what was happening, I only remember the feeling of boredom. It was disorientating, as we were bombarded by information and then rushed along before having time to digest it.

Ross' story is the centrepiece from which we branch off into the Silk Road, and further still into the Dark Web. It questions the morality of the authorities, and discusses libertarian philosophies, before arriving at Ross' trial, where even more questions are formed. With so much depth to each of these topics, why this wasn't made as a series baffles me. I don't fully understand firewalls, how am I meant to grasp the complexities of the varied levels of the internet after brief opinions from experts? By the way, there are three levels to the internet; the surface web, the deep web and the dark web. To put this into perspective, it is estimated that merely 4% of all content resides on the surface web.

Restrained by time, we barely scratch the surface of the FBI allegedly hacking into a foreign server without a warrant. Which has implications on the privacy rights of us all. The trial is confined to the final 15 minutes, where they skim over the judge's decisions, which border on sinister. Further still, the fact that two agents stole millions in bitcoin is limited to a few words on a screen.

While the narrative is jumpy, and the pace hurried, the story is still scintillating. It asks a lot of difficult questions. Some as complex as, what is really right? Some are darker. How can we fight back against these immoral institutions, such as the FBI, if they hold all the power? How can we protect ourselves digitally? What the Deep Web fails to do, is lead us in a direction to answer these. Opposed to feeling informed, I feel faintly afraid and quite frustrated.

It's worth watching to use as a stimulus to open your eyes and be more aware of the disturbing hierarchy we live within. And it's a fascinating subject, that asks a lot of questions. I just can't shake the feeling that it should have been more.

5.5/10