Despite being Head of Police in a town of around 30,000 people (according to Wikipedia), Clancy Wiggum has little to no understanding or respect for the law. Routinely ignoring emergency calls, arresting people on the flimsiest of excuses, and being too fat to function, it’s terrifying to think that he’s been entrusted with a gun.
To be fair, he does have his good qualities. His relationship with Lou and Eddie is a perfect model for friendships everywhere, and if Springfield can manage not to descend into anarchy with only 3 police officers, then he must be doing something right.
A snappy dresser, flamboyant libertine, and someone who checks whether guns are loaded by putting them in his mouth and pulling the trigger. He’s a great comic character, but not the best boss.
Proudly carrying on his dead father’s legacy, he’s created a toxic office environment of sexual harrassment and open bullying, yet somehow remains in the top position.
He’s incredibly incompetent, but his tailoring skills and fantastic collection of cowboy boots keep him from the top spot.
Head honcho at Sterling Cooper, functioning alcoholic, and clearly a very rich man. How did he get to such a position of power? By being the best drinker, smoker and philanderer in New York. If you work for Roger Sterling, he’s either about to have sex with you or fire you. There’s no inbetween.
Since the end of Mad Men series 5, he’s become a recreational LSD user, so who can tell what he’ll end up like as he moves onto harder stuff. SCDP wouldn’t last a day with a coked-up Roger Sterling wandering about the office, that’s for sure.
Arrested Development’s long-suffering CEO of The Bluth Company, somehow an even worse boss than his father, who spends most of the series in jail for tax fraud. Michael, despite his good-guy exterior, is actually fairly devious. He’s constantly playing his family off against each other, and when he’s not manipulating various women into sleeping with him, he’s consumed with impotent self-pity over how awful his family are.
Then again, you’d be a bit messed up if your brother was actually your cousin and your dad was too busy cheating on your mum to raise you.
A boss so terrible that it’s actually physically painful to watch him at work. Egotistical, untalented and woefully awkward, his name has become a byword for total incompetence. The Office is a comedy in the loosest sense of the word, because it can actually become a bit depressing to watch the sheer bleakness that he casts over the whole show.
The constant bullying he endures from his workers and superiors is a bit pitiful, but his sheer bull-headedness doesn’t make him that sympathetic a character. He’s also played by Ricky Gervais, so what’s not to hate?