Office Space (1999)
Cubicles, TPS reports, malfunctioning printers — Mike Judge’s cult classic nails the soul-crushing absurdity of corporate life. Ron Livingston stars as Peter, an office drone who decides to stop caring after a disastrous hypnosis session. With the help of his slacker coworkers (David Herman, Ajay Naidu) and the unforgettable Milton (Stephen Root), Peter finds rebellion in the little things — while Jennifer Aniston plays the waitress who proves there’s more to life than flair pins.

Hook: If you’ve ever fantasized about smashing your computer, ignoring your boss, or torching the office, Office Space makes it hilariously real.