Films
Which films get the culture right even when they bend the mechanics, and which ones to watch knowing exactly what they are.
Watch these for the culture, not the mechanics — all of them compress and simplify, and some of them are fiction throughout. Ranked roughly by how much of the job they get right.
The ones that get it right
Margin Call (2011). The best of them: a risk model returns an unacceptable number overnight, and the rest is people deciding what to do about it. Understated, dialogue-driven, and accurate about hierarchy in a way the others are not. If you watch one, watch this.
The Big Short (2015). The clearest popular explanation of CDOs and credit default swaps ever put on screen, at the cost of some caricature. Conceptually sound, and the fourth-wall explainers earn their place. Read the book for the mechanics.
Trading Places (1983). A comedy that ends in a commodities pit, and genuinely useful on how a corner works. Also responsible, indirectly, for a rule in US law about trading on misappropriated government data.
The ones about the culture
Wall Street (1987) and Money Never Sleeps (2010). Dated, and still the cultural template for the whole era — "greed is good" came from here, and was not meant as advice. Watch the first; the sequel is for completeness.
Boiler Room (2000). Pump-and-dump brokerage culture. More about sales cults than about trading, which is precisely what makes it useful: the pressure it depicts is real and has not gone anywhere.
The Wolf of Wall Street (2013). Stratton Oakmont at full volume. About excess and fraud rather than markets. Enjoyable, frequently mistaken for aspirational, and worth watching only if you keep that straight.