5. Office Space (1999)

Ron Livingston in Office Space

Before The Office came along and stole everyone’s hearts (the much more successful US version, not the UK original), there was Office Space. The 1999 film captured the essence of the modern daily grind, following a office worker dissatisfied with his life. It featured an all-star ’90s cast, including Ron Livingston, Jennifer Aniston, Gary Cole, Stephen Root, and John C. McGinley.

Office Space does more than just capture the spirit of office work: it effectively calls it out. It pokes fun at the typical characters that can be found in any modern office, proving both incredibly relatable and darkly funny. There’s also an element of wish fulfillment in seeing Peter break free from the constraints of the job he loathes.

Office Space takes the idea that office work saps the soul and runs with it. It paints an alarmingly accurate picture of career burnout and general dissatisfaction in life, then delivers a hopeful, positive, and borderline anarchistic ending. In essence, it’s something of a modern fairy tale, and it has a particularly dark sense of humor that made it one of the most subtle comedies of the decade.