From: Working Girl
Job Title: Financial Executive, Petty Marsh
One of the gravest sins of a bad boss is when they pretend to be on your side, only to steal your good ideas, which is just what Katharine (Sigourney Weaver) does to her new secretary Tess (Melanie Griffith). When Katharine breaks her leg, Tess seizes an opportunity to get revenge, stealing back her merger deal idea, along with her boss' job — and her man. "Let the River Run," indeed!
From: The Simpsons
Job Title: Owner, Springfield Nuclear Power Plant
With Homer Simpson as an employee, it's no wonder Mr. Burns has an evil streak. Still, the frail old man — who curls his fingers and mutters, "Excellent…" before doing anything sinister — uses his immense power and wealth to do whatever he wants to the occasionally good people of Springfield … some things so awful they can only really be captured in animation.
From: Glengarry Glen Ross
Job Title: Consultant, Mitch & Murray
Blake (Alec Baldwin) sure knows the benefits of negative reinforcement. When the ruthless salesman is brought in to "motivate" the less-than-impressive agents at a real estate firm, he literally dangles a pair of brass balls, imploring the men to obtain a pair of their own. He also coined the douchey ABCs of selling: "Always. Be. Closing."