3. HENRY LOEB

When you clean up shit for a living, any boss must be a horrible one; regardless of how pleasant he or she is, you’re still picking up after other people’s messes as a means of financial gain. But for Memphis sanitation workers in 1968, their boss, and the city’s mayor, Henry Loeb, was an asshole of the highest order.

Stuck on his racist power trip, Loeb punished his mostly black sanitation workforce with ridiculous rules such as allotting a mere 15 minutes for lunch and not allowing them to stand under trees when the sun became too overbearing. He also refused to listen to complaints about the employees’ run-down and problematic garbage trucks, an ongoing neglect on Loeb’s part that eventually led to two guys getting crushed to death and compacted into human garbage.

A massive sanitation strike went down after the fact, though Loeb, ever the prick, ordered cops to douse the protesters with tear gas and mace, even after the city council had come to an agreement with the workers. Needless to say, the shit had hit the fan.