Making a list for something like documentary of the network world and hacking stuff that all levels of computer engineers and hackers cannot miss to watch
Dr. Strangelove. There are at least a couple incidents in the movie where mundane technical failure contributes to catastrophe, and where technical safeguards that rely on "human in the loop" fail because of humans.
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The wikipedia article is itself as worth reading as watching the film. Bait: it mentions John von Neumann. https://en.wikipedia.org/wiki/Dr._Strangelove