The living embodiment of The Peter Principle. This is a person who has been promoted way beyond his level of competency. He or she may have had a clue at some point, but has since then misplaced it. Sometimes he is a Modern Major-General.
Very often such a boss is portrayed as not only incompetent, but also a little evil: the kind of guy who would steal credit from his employees and pin his failures on them. In these cases he can be more contemptible than the Corrupt Corporate Executive whom he serves; while the Corrupt Corporate Executive sold his soul for money, power and fame, an evil Pointy-Haired Boss sold his soul for nothing but a job little better than that of his employees, and doesn't seem bothered by it.
Occasionally he'll also hold the title of Benevolent Boss as well if his incompetence is more towards the job than his people skills; if he was very respected before The Peter Principle put him there his employees will likely cover for them.
All too often this is Truth in Television.
Films -- Animation
- Mr. Perkins, the evil head of the Bank of Evil (formerly Lehman Bros.) in Despicable Me certainly looks like the the original (or the unrated version of him) but he's actually scarily competent.
- Oscar's Fat Bastard boss, Sykes from Shark Tale.
- King Malbert the Fat Idiot from Igor.
- Lt. LaGuerta in Dexter got her job on talent for political maneuvering, and is in way over her professional head, showing no apparent ability as a detective. Her behavior toward subordinates could also qualify as harassment in some cases (such as her nowhere-near-subtle sexual overtures toward Dexter). This was introduced in the TV adaptation as well, but was gradually dropped over the first season and disappeared completely by the middle of the second, along with her infatuation with Dexter.
- Many of the Network Supervisors of the Bastard Operator From Hell series certainly are this, but it's semi-justifiable in that a position with such a high turnover rate probably doesn't particularly attract the employment agencies.
- Several of the officers in Sharpe.
- Vice-Chancellor Nesselrode is portrayed as this in The Death of the Vazir Mukhtar.
- Hamnpork, leader of the Clan in The Amazing Maurice and his Educated Rodents, may have been competent as top rat before they became "educated". Once the rats become sentient, he's too old to make the adjustment to thinking and becomes a bit of a figurehead, nudged into doing whatever Peaches or Darktan want him to. Played with, as he later shows just why he became leader of the Clan during a Badass moment in the Pit.
- George O. Smith's first "Venus Equilateral" story has a particularly memorable example... or at least a particularly memorable screwup by a PHB. The guy arrives, starts screwing things up and annoying people, tensions run higher and higher until there are pointless fights almost constantly... then an engineer swears, runs up to the center of the rotating station to get his bearings, then runs to the air plant - then runs to scream out the PHB. When the PHB arrived on the station, he'd done an inspection tour, and been confused by the air plant; he'd been expecting some manner of machine, but all he'd found was a big plot of sawgrass, so he had some workmen clear it out...
- The Phantom of the Opera: Deconstructed with Opera managers Richard and Moncharmin in the original book: Everybody knows they get their jobs thanks to their connections, that they play petty politics with the singers instead of recognizing their true talent, and they solve any problem firing those employees involved… except those who can defend themselves. Nobody really respects them and they are accustomed to cruel pranks, and that is the cause they never take seriously the Phantom’s menaces and think that Debienne and Poligny’s warnings are just a Practical Joke… until the Falling Chandelier of Doom incident.
- Falling Free: Bruce Van Atta: a former engineer, transferred to management where he would hopefully cause less damage. When Leo Graff sets off his plan to reconfigure the Quaddie's space station so that they can steal it, he tells Van Atta that he will be surprised by how much of the station, that Van Atta thinks is being decommissioned, can be "recycled." Van Atta insists that all of Leo's plans go through his office—so he can take Leo's name off them, and replace them with his own so he can take the credit.
- Lieutenant Colonel Henry Blake exhibited signs of this, as he was a good doctor but an almost criminally incompetent administrator. Radar practically ran the unit, only requiring Blake to sign off on documents. One time he got Blake to sign blank pieces of paper even as Blake railed about not knowing what he's signing.
- Blake was also completely aware that he was totally inept when it came to running the unit. He was completely competent when it came to make serious medical decisions (i.e. in the OR, or anything to do with patient care), but realized he didn't know what he was doing when it came to other administrative matters. To that end, he was completely happy to let Radar run things.
- The few times Frank Burns was put in charge, he was literally a criminally incompetent leader (as well as a doctor, but that's another trope there), bordering on Bad Boss turf.
- Hawkeye himself, while regarded as the best surgeon, did not do well when put in charge of the unit. Anytime that situation presented itself, his friends would have reactions in the realm of "oh god NOOOOO"
- Lieutenant Brass comes off very much as an incompetent and biased boss in the first episode of CSI, but it may just be that his promotion put him in over his head—when he is demoted to Homicide in the second episode, he becomes every bit the equal to the crime lab folks in professional competence. His demotion to a position of competence is actually a violation of The Peter Principle; something that is even rarer in real life than it is in fictional entertainment.
- Homicide: Life on the Street
- Detective Gharty is incompetent both as a beat cop and as the head of IAD, but turns out to be proficient when he finally lands as a homicide detective. When he is finally re-promoted to head the homicide division in the finale movie, he loses some of his competence again, becoming a shill for the department brass. It is noted that he's not entirely incompetent in the role, but in Giardello has some pretty big shoes to fill—and many of the other detectives note that "he ain't no Gee." Gharty is treated as a rather sympathetic case. While he is intelligent and capable, it has been shown on multiple occasions that he really isn't suited for the rough life of a Baltimore police officer and should have retired years ago (he has earned two citations for Bravery in the past). Gharty also seems painfully aware of how unsuited he is but still helps the main characters and tries to protect them from Gaffney.
- Averted cynically with Roger Gaffney. He is shown as an incompetent detective, especially when compared to the main characters and is rerouted to a dead-end department, but sleazes his way to a high-end position and gets the Captain's spot Gee had earned. Given the show's cynical view of the bosses, Gaffney fits in perfectly among men with even less moral standing than himself and who happily abuse power for their own ends.
- The bosses of The Office are exemplars of two different kinds of PHB. Michael Scott of the American version is a classic illustration of The Peter Principle: he was (and is) a genuinely superb salesman, but was promoted to the post of Regional Manager—a job he is absolutely unqualified for. His UK counterpart, David Brent, evidently never had any skills to begin with, making his promotion an enigma... or an illustration of the Dilbert Principle, wherein the incompetent are quickly Kicked Upstairs to a position where they will do less harm to the productive parts of the organization.
- Although it's not made as clear as in the American series, in the final episode of the British series it is suggested that Brent actually is a pretty good salesman, but is definitely not management material or as talented as he thinks he is. As for the enigma, Word of God responded to criticisms that Brent would never reach a management position with a retort that a brief look around any kind of corporate-style organisation (including The BBC) would reveal that major positions were being filled by people who were even worse than Brent.
- The laughably incompetent Colonel Klink of Hogan's Heroes. It's been mentioned that he's from noble stock, so he most likely got the position through nepotism more than any real leadership ability. He confirms in one episode that his family pressured him into the military to get rid of him. However, he is also a career officer with decorations for bravery in WW1; he used to be a pilot. It is almost certain he got promoted to his current position in an attempt to get rid of him, both as a bumbling fool and as a non-member of the Nazi party.
- Major Neuheim of Private Schulz is pretty much what Colonel Klink would be like if he was a die-hard Nazi.
- In 30 Rock, Jack Donaghy is promoted to oversee the production of Liz's comedy show after having invented a microwave. He seems to be a competent businessman, but clearly has no understanding of comedy. Note that he acted more pointy-haired in earlier episodes. This had all but disappeared by the second season. All of his summer shows were great hits, chief among them MILF Island.
Jack: I've been reading up on humor, I found this hilarious strip called Dilbert, and I want to know, can we do that?
- Captain Frank Hollister of Red Dwarf is revealed to have only reached his rank through blackmail (from the lowly position of Doughnut Boy no less), implying that he is possibly even less qualified than Rimmer or Lister (though clearly cleverer and/or more ambitious).
- The vacuous, hero-worshiping, management speak spouting Gus in Drop the Dead Donkey. He would appear to be a living, breathing example of the Adams principle.
- Dougie in Enlightened is a sort of example. While he is actually rather good at programming, his people-management skills are horrible, and he is pretty socially inept.
- ISO Administrator Mike Goss in Defying Gravity is shaping up to be this, grinding subordinates faces in their mistakes while refusing to admit to or back away from his own.
- The Brittas Empire revolves around one of these running a previously ordinary leisure center. Gordon Brittas (played by Chris Barrie) can, through sheer tactlessness and incompetence, induce psychological breakdown in pretty much anyone who visits the center. He stops by groups of happy people to offer well-meant "words of encouragement" and they storm off crying. He insults visitors until they're willing to pull a gun over a dispute about a cup of coffee. He tries to settle a problem with an unruly child, and ends up getting the center attacked by a Roman Recreational Society complete with war-elephants. His behavior did inspire many people to have the "I Spy Brittas" game where they have company outings to his center and score points every time they witness his various hand gestures and idiosyncratic tics and hear his various speeches. Bonus points if you get him to talk about The Dream.
- Arthur "Big Guy" Carlson, of WKRP in Cincinnati.
- In Are You Being Served?, much of the senior staff at Grace Brothers could fit this category. Mr. Rumbold is the most blatant example, but a recurring theme is that everyone in a position of authority at the store is incompetent; Captain Peacock is a blowhard, Mrs. Slocombe is far too self-absorbed to be much help to anything except for her pussy, Mr. Grainger is worn-out and well past the point when he should have retired, and Young Mr. Grace is virtually senile. Only Mr Humphries can handle additional responsibilities while escaping mostly unscathed.
- The Wire has several outstanding examples, both in city government and the Baltimore Police Department, with almost all authority figures fitting in somewhere between Corrupt Corporate Executive and Pointy-Haired Boss. Special note has to given to Maj. Valchek, however, who is rewarded for his incompetence by being made police commissioner.
- This is how Major Norton was portrayed in Disney's Davy Crockett mini-series, though he may have just seemed this way against Davy.
- In HBO's miniseries Chernobyl, Chief Engineer Dyatlov is portrayed this way due to his insistence to run the fateful security test that caused the explosion despite other plant personal trying to warn him that the conditions for that test were the incorrect ones, and then his stubborn denial that anything wrong ever happened at the place (even after, or maybe because of seeing the ruins of the exploded reactor) and trying to obstruct any action to control the disaster. In a scary turn, they only sightly exaggerated the antics of the real person, mostly by removing the mention of an incident that served as the Freudian Excuse for his radioactive stubbornness.
- The "bankers in charge" in Doctor Steel's "Lament for a Toy Factory."
- The Trope Namer comes from the original Pointy-Haired Boss in the daily comic strip and former animated TV series Dilbert, seen above playing chess against a 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 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 them are lesser reflections of the original. Interestingly the PHB was originally a unnamed balding manager who was more 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.
- Of course, he manages to get some pretty good evil moments in too.
- And some useful moments as well.
- 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.
- Ralph, Sally's original boss in Sally Forth.
- Rose Trellis (at least most of the time) in On the Fastrack.
- Many RPGs with diversified point-buy systems have characters suffering from PHB syndrome, especially if rank is among the characteristics to be bought. You can create a character that uses 95 of their 100 points on their traits and 5 on (e.g. military, noble or clerical) rank or you can use 80 points on traits and 20 on rank. Guess which character will be more competent...
- Paranoia has the CPU services. While every service has a few of these (read: everyone in it above the Troubleshooters' clearance, plus everyone at the Troubleshooters' clearance, plus the T-Shooters), only CPU will deliberately promote them.
- Department of Death Boss Don Copal in Grim Fandango might not have any actual hair, but if he did, it'd be pointy.
- Jeanne Frasoric, the head of the Bruma Mages Guild in The Elder Scrolls: Oblivion
- Cave Johnson from Portal 2 combines this trope with Mad Scientist for a Crazy Awesome blend of gross fiscal mismanagement, Inhuman Resources, and revolutionary super-science wasted because he can't figure out what it might be actually good for (e.g. using gel that bounces at 100% efficiency for a dietary supplement).
- The Magic School's Headmaster in Furmentation.
- Lord Stanley the Tool from Erfworld. He is not only is a Pointy-Haired Boss, he's a Bad Boss who threatens to kill Parson for simply noting that Stanley is short, and an Evil Overlord. And to top it all off? He believes that he is holy, and on a Mission from God (though in his defense, there's a good chance that he is). However, this may fall under the "promoted beyond his capabilities" aspect of the trope, as he's a pretty savvy tactician and capable warrior.
- The Noob has the head developer of Clichequest - the satirically stereotypical MMORPG that is set in and around - an idiot, Jerkass and a Small Name, Big Ego type to boot. And GMs he picks for the game tend to be, uh, like-minded.
- Mike in Between Failures is self-aware and trying not to be one of these, but his management training was inadequate to prepare him for the job, and those in charge of him have fobbed him off on one of the least important branch stores rather than trying to help him.
- George Fennec of Kevin and Kell is owner of Hare-Link, but only got that position because his daughter, the former owner, wanted to avoid a potential conflict of interest situation when her mother wanted her to promote her new stepfather. He makes hardly any useful decisions for the business except for once filling in for Kevin as a representative for a deal with Carrot Computers, and tends to be quite distracting. When he passes out after it dawns on him that his pregnant rabbit wife will likely have a litter of babies rather than just one, Kevin notes that they can finally get some work done.
- Horns, the Weapon Brown version of Dilbert's PHB is decidedly not like the original. For starters we're introduced to him as he's murdering Mr. Dithers to take charge of The Syndicate. Then again he forces the Mad Scientist version of Dilbert to rush CAL-v1.N and HOBS' awakening and ignores "Dilbert's" warnings that the two are unstable and uncontrollable.
- Mullet Boss from Basic Instructions fits this trope to a T
- Dr. Breign from The Snail Factory is the quintessential incompetent boss.
- Bug people have no hair - being bugs - yet you can spot the pointy-haired ones right away.
- SSDD explains the mechanics of how this happens here (and following pages).
- Principal Beau Vine in Ozy and Millie seems to not have the slightest idea how to properly educate children and run a school, sticking to the very outdated belief that bullying is a good thing and successively enacting and cancelling a school uniform policy several times in a single school year based on how popular such policies were at the moment, among other things.
- Shiny Objects Videos: The boss in "Magiconomy" is perfectly willing to banish his employees to the nether dimensions for making suggestions he doesn't like.
- The Dilbert TV series. See the Comics Strips section for more on Dilbert in general.
- Mr. Larrity from Code Monkeys outdoes perhaps even the Trope Namers; the man has no clue how to run a video game company (other than knowing that Games = $$$), generally treats his staff like crap, displays unapologetic sexism, has been known to do such outrageous things as bet Gameavision on a clearly bad Poker hand (that includes cards not even found in a standard deck of cards, like a blue Uno Reverse)... one could go on forever and not even scratch the surface.
- The Maurice LaMarche-voiced characters Principal Pixiefrog and Cheif are 100% this trope name.
- CatDog: Rancid Rabbit.
- Major Monogram from Phineas and Ferb drifts into this sometime. While most cases Doofenshmirtz is usually doing something to warrant sending Perry to stop him. There are a few instances where Doofenshmirtz is usually taking an off day such as going on a blind date, meeting an old teacher, going to a convention, actually being sick, etc., but Monogram doesn't really bother to look into these case and send Perry to "stop him" anyway. Then again, even in those occasions, Doofenshmirtz was doing something that should be stopped. In the blind date, Doof had developed a device to deprive people of their emotions if his date failed; to impress the "old teacher", he tried to blow up the moon; the convention was for evil scientists so, there was a reason to think someone (even if it wasn't Doofenshmirtz) would do something Perry should stop; when he got run over by an ice cream truck, he tried to hit the truck with a giant tire. Even when Major Monogram sent Perry to Doofenshmirtz because Doof was picking up empty bottles for recycling, it turned out it was for some plot ("It's green and evil! I call it 'greevil'!").
- Zapp Brannigan from Futurama, a celebrated space captain who couldn't fly his way out of a meteor shower. He puts all the work on his assistant Kif and takes any credit he can. His strategies for any threat are usually Attack! Attack! Attack!, sending hundreds of Red Shirts to their demise while he sits back and does nothing. The only reason he hasn't gotten himself offed  because circumstances usually prevent it from happening and at best he walks away with a few bruises.
- It really is just one, though
- other than that one time, but you know