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Pointy-Haired Boss

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The Pointy-Haired Boss is a character from Dilbert who while not always an active antagonist is well-known for his many flaws and general lack of sympathy for his workers - in the TV series the character is portrayed as slightly smarter (though still fairly idiotic) and more actively evil, arguably making him more of a villain than he is in the comic strips.

History

The Pointy-Haired Boss, sometimes shortened to the PHB, is Dilbert's boss and is infamous for his use of micromanagement and general inability to perform his job functionally - yet he somehow manages to retain his position regardless.

He can be very cruel and uncaring (shocking people with electric belts or wanting them to work 178 hours a week, although there are only 168 hours in a week — he expects his employees' families to contribute a few hours). Originally he only showed a few obvious signs of cluelessness but over the course of the series he became a complete idiot.

He is frequently childish, immature, ignorant and rude, yet also annoyingly cheerful and oblivious to his own actions. He frequently uses bizarre metaphors and analogies to "motivate" employees and (on the TV series at least) engages in rambling non sequiturs in conversation. In some strips, when he displays an above-average intelligence, or at least exhibits surprisingly original and cunning (albeit unethical or unscrupulous) thinking, Dilbert calls him a resourceful idiot. But most of his actions are incredibly stupid, including once using Moviefone to check on his IBM stock. At one time on the strip, the PHB recognizes that the biggest contribution that his department does to the company is actually the "brown table meetings", and that it is the only asset that prevents them from being outsourced.
He finds pointy hair as a positive and attractive feature - often judging people based on the pointy-ness of their hair, such as when he promoted an employee named Ted because of a pointy "beard" that was growing on his forehead, or when he became attracted to Alice because she styled her hair like his. The PHB also has a brother named Phil, the ruler of "Heck" (a subsidiary of Hell).

In an episode of the animated series, he sends all the engineers to mandatory ethics training camp, even though management had committed all the violations. He also had very poor knowledge of ethical guidelines.

He has little respect from workers, and their codename for him is "the stain". In a series of strips starting on 2/3/10 and ending on 2/15/10 he died. His secretary accidentally put his name in the fired box in the place of another recently fired employee. During the days that followed he enlists the help of Wally for hiding and eventually Asok. He tells the PHB to hide in the ductwork of the building and forage for leftover donuts at night. Once word got out of his hiding and apparent death, Alice and Dilbert built a device to shoot his carcass in the air. However, he was still alive, calling out for help. They chose to shoot him anyway, stating it would be a crime not to use the cool machine. After being shot, he lands on the wing of a plane. He is then put in a hospital, with the explanation that his pointy hair cushioned the blow. After Wally messes with his bed, he dies. He ends up in Helven, a mix of Heaven and Hell made since the demons and the angels unionized. At his funeral, Wally, Alice, and Dilbert are present to assure themselves that he's dead, and came with wooden stakes just in case. In the last installment, he is alive and well, explaining he was evicted from Helven, but not before bringing a demon consultant with him.

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