Cataloging Film and TV’s Worst Bosses

Don Draper, Mad Men

This one is kind of debatable. Yes, he’s brilliant at what he does. And in an office where the other two bosses are Bert Cooper and Roger Sterling, he often appears to be the sole voice of reason. But he also gets drunk in his office, disappears for long stretches of time, and makes a habit of bedding (or, you know, marrying) his secretaries. And need we even remind you of last season’s showstopping episode “The Suitcase,” in which Don makes Peggy stay late at work on her birthday and they fall asleep on each other, and it’s super-awkward because it’s clear Peggy has a better-hidden version of the same crush every other girl has on Don?