Hacking is about understanding, optimizing, and manipulating systems. One real-world analogue of a system is a Rube Goldberg machine; the dramatic analogue of a Rube Goldberg machine is a heist flick.
I'd add the Ocean's Eleven remake as an approachable introduction to the genre, and Kubrick's The Killing for vintage noir awesomeness. And maybe The Last Seduction as a curveball.