Deep Web
The Untold Story of Bitcoin and the Silk Road
Alex Winter's documentary on the Silk Road takedown and the Ross Ulbricht trial, with interviews from Wired's Andy Greenberg and others close to the case. Narrated by Keanu Reeves.
- Directors
- Alex Winter
- Released
- 2015
- Writers
- Alex Winter
- Runtime
- 89 min
- Language
- English
Available on
Watch this if
Anyone wanting the Silk Road story told from the defense and Ulbricht-family side, with court documents, family interviews, and dissent from the official narrative. Pairs with Nick Bilton's American Kingpin for the prosecution-leaning account.
Skip this if
Anyone wanting a balanced or skeptical account of Ulbricht specifically. Winter clearly sympathizes with the defendant; the film soft-pedals the murder-for-hire allegations and the broader cybercrime ecosystem the market enabled.
Key takeaways
- Silk Road was the proof-of-concept for darknet commerce, and the legal precedents from the Ulbricht case continue to shape how the DOJ argues about anonymous-network operators.
- Two corrupt federal investigators (Force and Bridges) stole Bitcoin during the Silk Road investigation; that subplot, which the film handles well, is one of the most underrated stories in cybercrime history.
- The sentencing (two life terms plus forty years, no parole) is the part of the case that has aged the most; the film makes the proportionality argument as well as anyone has.
Notes
Watch alongside Bilton's American Kingpin for balance; the truth lives between the two. Greenberg's reporting in Wired and his book Tracers in the Dark cover the underlying technical investigation in far more depth. The film's great strength is the family interviews, which no journalistic source has matched. The Ulbricht commutation (January 2025) post-dates the film and recontextualizes it; rewatch with that in mind.