Office Space on VHS. Starring Ron Livingston, Jennifer Aniston, David Herman, Stephen Root. With Ajay Naidu, Diedrich Bader, Orlando Jones. Written and Directed by Mike Judge. 1999.
The box says:
Overwhelmed by stress on the job, Peter Gibbons (Ron Livingston) goes in for therapy and comes out with a life-changing career philosophy: work sucks. Eager to begin a new life of unemployment, he decides to spend more time with his sexy girlfriend (Jennifer Aniston) and less time at the office. When he does show up, it’s only to play computer games, destroy company property and tell his boss exactly where to stick those meaningless memos.
But rather than get fired, Peter’s “straight-shooting” attitude leads him to a promotion! Now the stage is set to carry out a high-tech embezzling scheme that’s sure to mean the end of his job… and a one-way ticket to easy street. Can he pull it off before all corporate hell breaks loose?