The lighter side

Movies & TV:
- Snowden (2016) - Based on the true story of Edward Snowden, the CIA/NSA/etc whistleblower. Directed by Oliver Stone.
- Deep Web (2015) - Documentary (narrated by Keanu Reeves) about Ross Ulbricht aka. Dread Pirate Roberts and the infamous "Silk Road" dark market. Directed by Alex Winter.
- The Great Hack (2019) - Documentary about the Facebook–Cambridge Analytica data scandal. Thanks @woutfeys
- Mr. Robot - Hacker-drama starring Rami Malek. Producers hired actual hackers as consultants to ensure the show is as accurate as possible; real-world tools used in the show.
- Silicon Valley - Satirical tech comedy about a compression startup struggling to take off in Silicon Valley, California.
Podcasts:
- Darknet Diaries (by Jack Rhysider) - Highlights real-life hackers and their stories. Covers privacy topics a fair bit.
- The WAN Show (Linus Tech Tips) - Not specifically privacy, but they cover all sorts of tech news.
- The Privacy, Security, & OSINT Show - "This weekly podcast presents ideas to help you become digitally invisible, stay secure from cyber threats, and make you a better online investigator."
- Security Now! - "TechTV's Leo Laporte and I spend somewhat shy of two hours each week to discuss important issues of personal computer security." (Thanks u/Abaddon182)
Other:
- xkcd - They have comics for everything.
- System32 Comics Instagram and Reddit - Comedic computer comics.