The Wire
Seasons 1, 3, and 4 are an excellent class in gang culture, pragmatism, loyalty, and political intrigue.
True Detective Season 1
Horror vibes, subtle, slow investigations into conspiracies; damaged people interacting with each other
Peaky Blinders
Gang drama and how to build an interesting group dynamic (Season 1 and 2)
Burn Notice
Excellent guide to various useful skills, esoteric knowledge, and other useful pieces of trivial and spycraft.
House of Cards
Politics and Intrigue guide for assholes
Scandal season
1-2 (controlling the narrative over the truth)
Gossip girl season
1-3 (how gossip/rumor can destroy your enemies)
Re:zero
(royal selection episodes—how to negotiate with limited information)
Leverage
How to do exploitation and coercion.
Movies
Training Day
Deception, planning, and intrigue how to movie
Dangerous Liaisons
Good for high society social dynamics, plotting, and betrayal
Interview with a Vampire
A classic example of Victorian vampire drama, and highlights a lot of the struggles vampires deal with over living for centuries
The Thomas Crown Affair
Fun caper film that focuses on avoiding direct confrontation and being subtle, sneaky, sly, etc.
John Wick 1 & 2
Good in theme of how boons, elysium and similar should work in the WoD
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