Season 6 of Criminal Adaptations is almost here.

This season, we’re diving deeper into the real crimes behind the movies. Unpacking the true stories, the courtroom drama, the scandals, and the cinematic twists that brought them to the screen.

From shocking real-life cases to the films that reimagined them, Season 6 explores how Hollywood transforms crime into culture.

Subscribe now and get ready. New season dropping soon.

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Two films, one real-life National Security Agency (NSA) whistleblower, and a story that blurs the line between truth and fiction. In part two of our season finale, we dive into two very different films: Reality (2023), the HBO American crime drama directed by Tina Sater and staring Sydney Sweeney, and Winner (2024), the black comedy directed by Susanna Fogel, staring Emilia Jones, Connie Britton, and Zach Galifianakis. The films offer two very different cinematic interpretations of the life and arrest of Reality Winner, a former US Air Force linguist turned NSA contractor who leaked top-secret documents about Russian interference in the 2016 presidential election.

We unpack how each film portrays Winner’s character, choices, and the forces that brought her from military service to a leak that made national headlines. Next, we contrast those portrayals with the real events – from the NSA leak and Federal Bureau of Intelligence (FBI) investigation to her 2018 guilty plea and five-year sentence under the Espionage Act, the longest such punishment for unauthorized media disclosure in recent history. Whether you’ve seen the movies, followed the headlines, or are just curious about the real woman behind both scripts, this episode peels back Hollywood’s layers to reveal the truth beneath.

Primary Sources:

• Howley, Kerry. Bottoms Up and the Devil Laughs: A Journey Through the Deep State. Knopf (2023).
• Winner, Reality. I Am Not Your Enemy: A Memoir. Spiegel & Grau (2025).
• NSA Document

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The movie Snowden (2016) presents the protagonist as a reluctant whistleblower who sacrifices everything to expose government surveillance – but how closely does the film match the real man and case? In part one of our two-part season finale, we break down Oliver Stone’s biopic, staring Joseph Gordon-Levitt and Shailene Woodley, alongside the true story of Edward Snowden, the former National Security Agency (NSA) contractor whose leaked documents revealed the scope of mass surveillance in the United States and beyond.

We examine Snowden’s background, motivations, and personal relationships as portrayed on screen, then compare them to the documented timeline of events – from his work inside the intelligence community to the moment he decided to go public. We also look at what the movie emphasizes for emotional impact, what it simplifies or leaves out, and how political beliefs shape the way this story is told. Ultimately, this episode asks whether Snowden (2016) is a faithful retelling, a political statement, or something in between – and why the real-world consequences of the case continue to matter today.

Primary Sources:

• Washington Post (2014)
• New York Times (2015)
• The Times (2015)
• Snowden, Edward. Permanent Record. Picador Paper (2019).
• United States of America v. Edward Snowden (2019)

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