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.
Antitrust (2001) http://www.imdb.com/title/tt0218817/