If you've ever worked for somebody else, you know that inept bosses are not entertaining company. It's different on TV, though, where some of the most beloved characters in recent TV history are inept bosses, including Michael Scott, Steve Carrell's character on "The Office." In some ways, these inept bosses represent a kind of unattainable fantasy: they're incompetent, sure, but they're also funny, and no main character ever seems to get fired. In other words: maybe you'd be a little better off if you did work for one of these guys.
George Steinbrenner, "Seinfeld"
One of the only TV bosses to be based on a real boss, owner of the New York Yankees George Steinbrenner on "Seinfeld" appears to have a management style that can be described as "stream of consciousness." Whatever pops into Steinbrenner's head becomes official New York Yankee policy, and it's often George Costanza that has to carry these ridiculous schemes out. This is what's known in science as a "perfect storm of stupidity."
Pointy-Haired Boss, "Dilbert"
On the sadly short-lived animated series based on the "Dilbert" comic strip retained the comic's pointy-haired boss, and the boss's idiotic management techniques. He's basically a symbol for every inept boss in the world, and nothing he does is too stupid or literal minded. There will come a day when real-world bosses catch up to the PHB's stupidity, but luckily, that's probably at least two or three months away.
Arnold Rimmer, "Red Dwarf"
Just because you've never passed the test to become an officer doesn't mean you can't be somebody's inept boss, providing a massive cataclysm of the space station you work on obliterates everybody on board, and by sheer process of elimination you become the ship's commanding officer. This is what happened to Arnold Rimmer, hologram/commanding officer on board the SS Red Dwarf. He's arrogant, egotistical, and a little stupid, but you can't help but like him anyway. Who cares that he caused the radiation leak that killed the entire crew?
Murray Hewitt, "Flight of the Conchords"
Here's an inept boss who's barely a boss at all. His position as the manager on Flight of the Conchords, a folk duo from New Zealand, is more like a hobby than a job, given that he also works at the New Zealand embassy. Murray's ineptness and oblivousness know no bounds, arranging the band to be paid in soup, and hiring a Barack Obama lookalike to meet with the president of New Zealand (he's inept in his day job as well). For the trifecta, Murray is inept in his personal life, too. He's a triple threat!
All of Jack Bauer's bosses, "24"
Fans of the real-time action thriller series "24" that the bosses on the series only exist to get into super-agent Jack Bauer's way. These bosses range from squirrelly micro-managers at Counter Terrorism Unit, to cowardly and politically-motivated Presidents, to actual terrorists that have infiltrated the government. The point is, anyone who doesn't give Jack Bauer carte blanche in the terrorist-killing business is a special kind of inept.
Roger Sterling, "Mad Men"
Most of the bosses at advertising agency Sterling-Cooper-Draper-Pryce are at least somewhat competent at what they do (or used to be). But nobody's really clear on what it is Roger Sterling does. His dad started the business, and while he's got a quick wit, advertising is not really his game. He puts dozens of staffers out of work after a merger that was purely to fund his divorce, and he appeared at a company picnic in blackface. Even in the 60s, that's not kosher.
In their own ways, these TV bosses are even more inept than Michael Scott. Remember them next time you have to deal with your moron of a boss. Careful, he and/or she is behind you! Just kidding.