Darknet Diaries! Fantastic show about all kinds of stuff, from cyberheists to pentesting to other crimes.

In the same vein, the two-season Lazarus Heist from the BBC is a deep dive into North Korea's assorted cybercrimes (including trying to plant employees at some crypto exchanges), and is riviting.

Dan Carlin's Hardcore History is an amazing deep dive (each episode can run 5-6 hours, and he released 2-4 episodes a year) into history from a non-historian's perspective.

And one I love that's a little lighter:

You Must Remember This: A look at classic Hollywood, ranging from the early days all the way to the '90s. Incredibly well-researched.