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* The [[Trope Namer]] comes from the original [https://web.archive.org/web/20070704114838/http://www.unitedmedia.com/comics/dilbert/the_characters/ Pointy-Haired Boss] in the daily comic strip and former animated TV series ''[[Dilbert]]'', seen above playing chess against a [[Fundamentally Funny Fruit|pineapple]]—and ''losing''. (Count the captured pieces!)
** According to Scott Adams's 1996 book ''[[The Dilbert Principle]]'', the truly Pointy-Haired Boss is a reflection of the ''abandonment'' of the aforementioned [[The Peter Principle|Peter Principle]]. In the past, competent people were promoted until they reached a position just barely overreaching their talents; now, however, the ''absolutely'' incompetent are ''immediately'' [[Kicked Upstairs]]—where, kept out of contact with the customer base and daily work load, they will do the least harm.
** Adams draws just about ''every'' manager with pointy hair. A minimum of 99% of [http://dilbert.com/strip/2003-10-16 them] are lesser reflections of the original. Interestingly the PHB was originally a unnamed balding manager who was more [[Characterization Marches On|cruel than stupid]]. Then one day Adams accidentally drew the hair on the sides of his head slightly pointy and thought the resemblance to devil horns to be eerily appropriate. Then he started making him gradually more stupid while his hair kept getting pointier. And the rest is history. There's been the odd strip that actually ''sympathizes'' with the PHB and have him getting angry or frustrated for good reason. Presumably such instances come from the occasions when Adams solicits ideas from his readers, and a boss or manager was the one who got his attention.
** Most strips actually are reasonably sympathetic to the PHB, inasmuch as it's not ''his'' fault he's woefully incompetent. Catbert is more explicitly antagonistic; the PHB is just trying to be a manager and failing horribly at it.
** [http://dilbert.com/strips/comicstrip/2006-10-06/ Of course, he manages to get some pretty good evil moments in too.]
** [http://dilbert.com/strips/comicstrip/2004-08-29/ And some useful moments as well.]
*** PHB occasionally ''does'' [[Dumbass Has a Point|make an excellent point]]. [//dilbert.com/strip/2011-02-20]
** Adams himself, when running a restaurant, realized that he was becoming a Pointy-Haired Boss himself, albeit a relatively benign one.
* In ''[[Retail]]'', just about anybody at the level of store manager or higher is portrayed as a PHB.
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