Adam Markovitz
July 15, 2011 AT 04:00 AM EDT

Heartless
Buddy Ackerman, Swimming With Sharks (1995)
Years before Horrible Bosses, Kevin Spacey played a Hollywood mogul from hell in this dark indie comedy.

Franklin M. Hart Jr., 9 to 5 (1980)
The sexist pig (Dabney Coleman) gets offed by his workers in a lethally funny dream sequence.

Katharine Parker, Working Girl (1988)
Sigourney Weaver chews scenery as an exec who backstabs her assistant (Melanie Griffith).

Harmless
Miranda Priestly, The Devil Wears Prada (2006)
Meryl Streep’s fearsome editrix has a heart — she’d just never wear it on her couture sleeve.

Bill Lumbergh, Office Space (1999)
Weekend work is the worst you’ll get from this irritating middle manager (Gary Cole).

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