Pointy-haired boss: I saw the code for your computer program yesterday. It looked easy. It's just a bunch of typing. And half of the words were spelled wrong. And don't get me started on your overuse of colons. Dilbert:They remind me of you, sir.
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 immediatelyKicked 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. Then there's the CEO of the company - the guy who the Pointy-Haired Boss reports to - who's just as incompetent as he is, if not more so.
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.
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 Bad Ass moment in the Pit.
Night Watch gives us two examples in the past version of the title organization. The first is Captain Tilden, a decent enough man who was a competent military leader, but is woefully unqualified to run a police organization. The (largely corrupt) Watch runs rings around him. Later on he is replaced with the future Lord Rust, a General Failure who is a far more dangerous sort of stupid. Vimes winds up laying him out with a single punch and effectively taking command himself (which he was arguably doing anyway under Tilden).
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...
For those of you wondering what the problem was. the plot of sawgrass was the air plant: it filtered and scrubbed the air simply by being sawgrass.
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.
In Thirty 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?
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 Brittas Empire revolves around one of these running a previously ordinary leisure center. Gordon Brittas (played byChris Barrie) can, through sheer tactlessness and incompetence, induce psychological breakdown in pretty much anyone who vists 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.
Lieutenant Brass comes off very much as an incompetent and biased boss in the first episode of CSI: Crime Scene Investigation, 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 more rare in real life than it is in fictional entertainment.
This is how Major Norton was portrayed in Disney's Davy Crockett mini-series, though he may have just seemed this way against Davy.
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 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.
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 World War I; 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.
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.
Denholm Reynholm, and even more so his son Douglas, in The IT Crowd. The latter once checks to see whether a gun is loaded by sticking it in his mouth and pulling the trigger. In another scene, he picks the king of diamonds from a magician's deck; when the magician asks if it was the ace of diamonds, Douglas is impressed at how close he got.
In Made In Canada, Pyramid Productions CEO Alan Roy has no idea how to properly run a film and television production company. His management style is based on reading (but not understanding) best-selling business books, and his ideas for how to "improve" the various films and television series made by Pyramid are universally inane and/or inappropriate (such as re-casting a fly-on-the-wall reality series with himself and two other Pyramid executives as the contestants (leading the series to be cancelled), or lightening the tone of a gritty detective series to such absurd levels that an episode about a murdered prostitute is re-written to focus on a lost kitten (leading that series to be cancelled)).
Lieutenant Colonel Henry Blake exhibited signs of this, as he was a good doctor but an almost criminally incompetent administrator (though not quite as dim as in the movie). 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.
The few times FrankBurns 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!" That said, Hawkeye was perfectly aware that he had no talent for leadership and tried to refuse command.
A Mr. Show sketch about downsizing features a boss (played by Tom Kenny) who ends up firing many of his employees in order to boost profits . . . then notices he's the only one sitting at the table. Realizing he's the only one left, he goes mad from the isolation until his assistant brings him back to earth. He thanks her then fires her.
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. Though he could be guilty of being an Evil Boss at times, his employees were generally competent and sometimes backed him when it was important enough. His evil tendencies faded over time, but his general inability to manage remained. 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 (see below), 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 organization (includingThe BBC) would reveal that major positions were being filled by people who were even worse than Brent.
Major Neuheim of Private Schulz is pretty much what Colonel Klink would be like if he was a die-hard Nazi.
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 Television version of Stuff You Should Know features Steve, a rare female example. She keeps order in the office by fostering paranoia among the other staff, and switches show priorities based on her daily whims and complete misreading of social trends. She's somewhat of a more effective manager than others on the list, but that could be because the rest of the office is just as crazy as she is.
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.
Carlson's mother put him in charge of her station specifically so it would lose money and be used as a tax write-off for her corporation. When the new program director changed the format and the station started to make money, she wanted him fired.
"As God is my witness, I thought turkeys could fly."
The "bankers in charge" in Doctor Steel's "Lament for a Toy Factory."
Dino Attack RPG has Elite Agent French Fries, who made several incredibly poor choices that had disastrous consequences. Of note are his decision to expose the previously top secret campaign in Antarctica (at first seeming like a good idea, only to accidentally cause massive riots and escalate the already mounting tension between the idealist and realist sides of the team into a whole new level of violence). Later on he attempted to perform a court martial against George and Rotor with conflicting charges, implement a "brilliant" idea that involved everyone walking very slowly toward a horde of mutant dinosaurs, and finally got beaten up by several different people for his trouble.
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.
The "BrikWars" rulebook 2005 and 2010 has a picture of a pointy haired minifig holding a piston to illustate half-minds. Curiously, The he was illustrating the cleverer mind, the other minifig was holding the pistol to his face.
Department of Death Boss Don Copal in Grim Fandango might not have any actual hair, but if he did, it'd be pointy.
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. marketing gel that bounces with 100% elasticity as a dietary supplement).
Nobles in Dwarf Fortress tend to be like this. For instance, nobles will periodically ban and unban the export of their favorite types of materials (like iron). So, if the noble has recently unbanned the export of iron, you might take the chance to sell some iron items to a caravan... only to have the noble re-ban iron after the caravan has packed up and is heading off, but before they disappear off the edge of your settlement. Once that caravan disappears off the edge of your settlement, whoever helped export the iron will be punished.
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.
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 & 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 onenote It really is just one, though, 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.
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 note other than that one time, but you know because circumstances usually prevent it from happening and at best he walks away with a few bruises.
Fry became a literal one of these when... That 80s Guy bought out Planet Express and promoted Fry to the position of Vice Chairman simply on the fact that they were both from the 80's.
Earl of Lemongrab from Adventure Time. He's the heir to the Candy Kingdom Throne because he was created by Princess Bubblegum in her laboratory to take the throne if anything should happen to her. But, being "the first one of her experiments gone wrong," he's a horribly incompetent ruler- immature, misguided, persnickety beyond all reason, a total stresscase, a Jerkass, and a mentally dysfunctional idiot with an almost pathological obsession with sending people to the dungeon for incredibly petty reasons. Princess Bubblegum strongly dislikes Lemongrab, everyone is annoyed by him, and he doesn't even want the job anyway- it was assigned to him when he was created.
Pops from Regular Show is this. He's the boss at the park, but he's incompetent, childish, clueless, and very naive. However, unlike most examples of this trope, he's a Benevolent Boss. He's an incredibly sweet man, and always has a kind word for everyone. Everyone at the park really likes him, even though he's an oddball.
Heavly lampshaded with Randy Marsh in the South Park episode, "A Nightmare on Facetime".
Malory Archers boss/mom who's mind tends to fly on missions, and sometimes becomes an emotional wreck.
Happens to the KGB as well in season 3. Not that Major Jakov was especially competent, but he is eventually replaced by Barry Dillon, a former Odin agent rebuilt as a cyborg. Which might be fine, as Barry was good at his job, but becoming a cyborg seems to have exaggerated his Bunny-Ears Lawyer tendencies into full blown insanity. He has since been replaced by Katya Kasanova (also a cyborg and former agent), and it remains to be seen how competent she is.