Film
Deep Web
A documentary about Ross Ulbricht's arrest as Silk Road's operator, narrated by Keanu Reeves. It's part true-crime procedural, part manifesto for digital privacy and libertarian ideology. Slick, propulsive, and unapologetically sympathetic to its subject—designed to make you question whether the prosecution was just, or whether we sacrificed privacy for security.
Should you watch it?
Watch it if you enjoy true-crime stories set on the internet's shadier edges and want to hear the people inside them, the family included, speak for themselves.
Skip it if you want a balanced inquiry, since it argues its case with evident sympathy for its subject and spends much of its runtime on digital-rights arguments.
What it asks of you: At just under ninety minutes it stays brisk and talky, leaning on interviews and narration, so it asks for steady attention more than prior knowledge of crypto.
Not sure? Find tonight's pick in a minute.
If you liked this
The Social Dilemma2020
Explores how tech platforms shape behaviour and society at scale, with the same concern for digital autonomy that Deep Web champions. Features engineers and executives from inside Silicon Valley breaking ranks.
But Feels occasionally preachy and simplifies complex incentive structures into good-guy/bad-guy narratives.
Citizenfour2014
Laura Poitras's Oscar-winning doc about Edward Snowden unfolds with comparable tension and philosophical weight. It's about surveillance, secrecy, and the price of dissent—themes Deep Web orbits.
But More austere and sobering; less interested in narrative momentum or vindication.
American Animals2018
A heist doc that reconstructs a rare book theft with surprising philosophical ambition. Questions memory, motivation, and whether the crime or the mythology matters more.
But Shifts between documentary and dramatisation in ways some find gimmicky rather than illuminating.
Not sure tonight? Get a pick in a minute, starting from Deep Web
The wildcard
Something you would not have found on your own.
The Stanford Prison Experiment2015
Both examine how ordinary people become trapped in systems larger than themselves, and question whether the institutions investigating them are any more ethical.
A dramatisation of Zimbardo's infamous 1971 study about power and systems gone wrong. Like Deep Web, it's about bright people caught inside a structure that corrupts and consumes them—and about institutional failure to see what's happening.
But The film itself came under scrutiny for dramatising something already controversial; it's less about the experiment than the mythology around it.
More like this (6)
The Toys That Made Us2017
Each episode traces how a product became cultural infrastructure. It's intimate corporate archaeology—understanding systems through the people who built them, not just the outcomes.
But More nostalgia than critique; glossy rather than investigative.
Winter on Fire: Ukraine's Fight for Freedom2015
A visceral on-the-ground account of protest and state power. Like Deep Web, it follows individuals caught in a larger conflict over the shape of society.
But Emotionally exhausting; less sympathetic to complexity or ambiguity.
AlphaGo2017
Documents the creation of AI that defeats a Go champion, exploring what genius looks like when it's not human. Shares Deep Web's fascination with brilliant people and transformative technology.
But More celebration than interrogation; doesn't question whether this progress is wise.
The Great Hack2019
Investigates Cambridge Analytica's data manipulation and the 2016 election. Paranoid, intricate, and genuinely unsettling about privacy and digital power.
But Sometimes overdramatic; conflates complexity with conspiracy.
Lo and Behold: Reveries of the Connected World2016
Werner Herzog meditates on the internet's meaning through conversations with engineers, activists, and experts. Dreamlike and philosophical where Deep Web is argumentative.
But Slow, digressive, and occasionally self-indulgent in a way that obscures rather than clarifies.
In the Realm of the Senses1976
Both are products designed to be controversial, asking viewers to reconsider where they draw lines around permission, censorship, and state power—and whether those lines are defensible.
An explicitly transgressive 1976 film about desire, autonomy, and a relationship that defies state and social control. Like Deep Web, it's uncompromising about challenging what society deems permissible.
But Graphic sexual content throughout; deliberately provocative in a way that will alienate many viewers.
People
Cast
Keanu ReevesNarrator
Ross UlbrichtSelf
Cody WilsonSelf
Lyn UlbrichtSelf- Kirk UlbrichtSelf
Andy GreenbergSelf- Nicolas ChristinSelf
- Cindy CohnSelf
- Todd ShipleySelf
- Alden SchillerSelf
Directing
- Alex WinterDirector
Writing
- Alex WinterWriter
Production
- Bree Polk-BaumanAssociate Producer
- Damir OmicAssociate Producer
- Valerie BishopAssociate Producer
- Andy GreenbergConsulting Producer
- Thom ZimnyConsulting Producer
- Jill BurkhartExecutive Producer
- Ross BernardExecutive Producer
- Seth GordonExecutive Producer
- Alex WinterProducer
- Glen ZipperProducer
- Marc SchillerProducer
- Devorah DeVriesSupervising Producer