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The Worst Bosses Of All Time (PHOTOS)

First Posted: 3/18/10   Updated: 5/25/11

Most of us have experienced the dumb boss, the arrogant boss, the mean boss. But, as the accompanying collection of famous business tyrants illustrates, it takes a certain special something to rank as one of the worst bosses of all time.

Specifically, we're thinking of bosses who coerce you into into doing their yard work, bosses who throw phones at you, or those who (reportedly) try to make you kiss a coworker. The stories of legendary despots like Vogue's Anna Wintour or the cantankerous billionaire Sam Zell are so widely known, they've almost become acceptable. (Well, not quite.)

Take a look at the soul-crushing antics of some of the most notorious employers in our slideshow of malicious bosses. But, if you've got horror stories of your own, we're all ears! Email us with your worst examples of how a boss has treated you, flown off the handle or otherwise made your life a living hell. Send your stories to HuffPost-At-Gmail-Dot-Com -- we'll be building a list of your most awful anecdotes.


Anna Wintour
 
When there is a bestselling novel and movie about your cruel behavior in the work place, that can only mean one thing: you're a legendary work despot.  While Wintour’s inclement personality is certainly fitting for the industry in which she works, employees are reminded not to look her in the eye for fear of her wrath.

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Most of us have experienced the dumb boss, the arrogant boss, the mean boss. But, as the accompanying collection of famous business tyrants illustrates, it takes a certain special something to rank as...
Most of us have experienced the dumb boss, the arrogant boss, the mean boss. But, as the accompanying collection of famous business tyrants illustrates, it takes a certain special something to rank as...
Filed by Claire Schneiderman  |