A Sadist Teacher in charge of an entire educational institution. This guy hates the protagonist and his friends — especially the High-School Hustler — with a passion. He has the entire institution with its long history and dignified reputation on his side. Its arbitrary and ancient rules exist chiefly for him to abuse in his vendetta.
Dean Bitterman is a pompous, self-absorbent and sour old killjoy who is opposed to the merest hint of fun. He believes that it cheapens the good name of the institution. However, don't expect this disdain to be evenly applied; he'll suck up shamelessly to wealthy parents. He favors the children of alumni and big donors. He has no problem with letting them get away with murder. He is quite blind to their obnoxiousness and malevolence — and the fact they are much worse than the heroes would ever be. In lay terms, Double Standard is on full display on his watch.
If you don't come from old money or have a trust fund, or even if you just happen to be in a fraternity or sorority that he disapproves of, then heaven help you.
If Dean Bitterman is temporarily taking the place of a more likable character, then he is starring in a Tyrant Takes the Helm story arc. The classic Dean Bitterman is found in colleges and universities. Sometimes he turns up in high schools, where he will be the principal of the school (or in some cases, the vice-principal acting as The Dragon to an ostensibly more pleasant principal, who may have selected him or her specifically to be their ax-man).
The Dean Bitterman is the ideological nemesis of the High-School Hustler, who may not make it a life mission to irritate the Dean and subvert his authority at every opportunity, but still does. Expect the Hustler and his friends to be expelled at some point, only to take their elaborate revenge in the climax.
In Real Life, while college faculty and rules on college campuses can obviously be biased, most deans and headmasters are far too busy and in charge of far too many students to have personal vendettas against a small set of them. Educational institutions typically have written rules and codes of conduct. Any dean that expels a student for reasons he created by fiat should expect several lawsuits.
In terms of rank, the Authority Tropes arguably at the next step down are Badass Preacher, Corrupt Corporate Executive, Irish Priest, Preacher Man, Pedophile Priest, Schoolteachers, Sinister Minister, and The Vicar. For the next step up, see Majorly Awesome. Contrast Putting the "Pal" in Principal.
- Akkan Baby: To an extent, the new principal at the school. She bans electronics, makeup, shortened skirts, and jewelry, and even tries to ban male-female contact. Cue Yuki bursting in late, carrying Shigeru (whose skirt is extremely short) - and then ends up blurting out she's pregnant. It doesn't end well. However, considering how the students at the school are delinquents or act like the part, she's a more justified case.
- Great Teacher Onizuka: Vice-Principal Uchiyamada hates Onizuka and will stop at nothing to get him fired, even though his class increasingly likes their teacher's unorthodox methods. (To be fair, Onizuka did wreck his car 3 times, but Uchiyamada already had it out for him. And two of those times were accidents). Fortunately for Onizuka, the Chairwoman Ryoko Sakurai is in charge of hiring and firing decisions, and she seems to like him.
- Major 2nd: The Principal of Fuurin Academy seems to be bent on making a living hell for Daigo Shigeno and the baseball club as a whole. To wit, the school's baseball team was caught in the middle of a scandal that resulted in most of the second-year players being expelled and the coach resigning, leaving the club down to only five members, and Daigo having to do double duty as team captain and coach. When it seems a new coach will come to their school, the principal rejects his offer, and the team barely makes the cut when a few new first-years join to make a full active roster. Add to it that he appointed as the club's advisor a teacher who is rather apathetic and actually hopes the team loses so she can go home and be relieved of these duties. And when Daigo's father Goro wants to offer himself as a coach, he's also rejected because he's still active as a professional player, and thus cannot legally take that job. Things begin to make sense when it's revealed that the principal is none other than Tetsufumi Egashira from the original Major series, who is still bitter about his plans for Kaido Academy being ruined by Goro, and now seems to be taking revenge on him through his son.
- Robin: Dean Nederlander of Brentwood Academy is a suspicious old man who patrols the campus at night and gives out demerits like candy, and it doesn't take very many demerits to earn an expulsion. He is however somewhat reasonable and his attitude can be explained by just how many of his students are there because they're troublemakers who've been expelled from other schools.
- Headmaster Hammer of Gotham Academy is a cranky elderly man who keeps confiscated student possessions in a dusty trophy room and takes joy in "expelling Waynes" and other students, though he does allow them to present a case for remaining (unless they're Waynes).
- Miles Morales is about to swing to the adventure... hey, where do you think you are going? You have chemistry class! The dean is not an idiot, and has his eye on you!
- Wonder Woman vol 1: Dean Strikt of Holliday College, also known as Dean Sourpuss, was exasperated with their students' antics and had little patience for perceived trouble making. She was also incredibly protective of them and supportive of their goals, but loafing around on campus while one was meant to be in class, pulling pranks or looking like one was going to pull a prank was a good way to get a long lecture entirely screamed in one's face.
- Star Wars: Doctor Aphra has the Sava, or teacher, who accepted Aphra into his doctoral program. He says he did it merely to give her hope and take it away all because he hates her.
- In Peter Parker's Field Trip (Of course it's to Stark Industries), Principle Morita is completely on Harrison's side in regards to Peter being a liar, suspending Peter from all school activities for it.
- Principal Mazur in A Goofy Movie wants to plan events during summer vacation that involve coming to school and learning. He also tells Goofy that Max was dressed like a gang member (actually a celebrity), and started a riot (actually just people having fun at an assembly due to his surprise music show), and says he'll be arrested and executed eventually, unless Goofy changes something about his parenting. To put it in perspective, this mindset is otherwise held only by the character who believes the proper way to raise a child is to bully him.
- Principal Cinch of Crystal Prep Academy in My Little Pony: Equestria Girls Friendship Games. She doesn't really detest her students, but sees them as tools instead of people, tools by which she can forge her reputation and legacy on. This mentality also spreads to the rest of the school and makes everyone haughty and uncaring towards one another, uninterested in anyone's accomplishments but their own. Interestingly, the schools' actual dean, Cadence, is quite nice.
- Dean Vernon Wormer in Animal House. However, since the film is much more cynical than later Wacky Fratboy Hijinx films, he often comes across as a Villain With A Point, and the Deltas really are engaging in "pranks" that no sane college administration would tolerate.
Fat, drunk and stupid is no way to go through life, son.
- The Dean from Harold Lloyd's 1925 film The Freshman, said to be so formal, he never got married because he was afraid his wife might call him by his first name.
- Our Miss Brooks: In The Movie Grand Finale, Miss Brooks meets Mr. Conklin on her first day at school. He makes it understood that he is a man of a military background, who runs Madison High School with discipline. And immediately Miss Brooks drops a barbell on his foot . . . .
- Van Wilder's Professor McDoogle pretends to be one of these, but he's actually a Stern Teacher specializing in the Secret Test of Character — the only reason he was riding Van was to make him realize his potential.
- PCU has the dean trying to shut down "the Pit," a frathouse full of slovenly hipster deadbeats.
- Principal Dick Vernon in The Breakfast Club, although it's deconstructed somewhat in his conversation with the school janitor.
Vernon: Carl, I've been teaching for twenty-two years. And, each year, these kids get more and more arrogant.
Carl: Aw, bullshit, man. Come on, Vern. The kids haven't changed; you have. You took a teaching position because you thought it'd be fun, right? Thought you'd have summer vacations off. And then you found out it was actually work, and that really bummed you out.
Vernon: These kids turned on me. They think I'm a big fucking joke.
Carl: C'mon listen, Vern, if you were sixteen, what would you think of you, huh?
Vernon: Hey, Carl. You think I give one rat's ass what these kids think of me?
Carl: Yes, I do.
- The same principal also appears in Not Another Teen Movie (with the same actor, even). Like many other things in the film, he is exaggerated for laughs, with a colossal desire to be "bitter" but having an equally colossal degree of incompetence.
- Dean of Students Edward Rooney from Ferris Bueller's Day Off. Though his hatred seems to be concentrated solely towards the title character and his friends.
- Dean Richard Van Horne in Accepted is the polar opposite of Bartleby and his friends, as he discourages innovation and loosely regulated education. His personal belief is that a college's prestige is measured by how many applicants it rejects every year. Also, his motives for taking down the college have nothing to do with college honor or any of that. He just wants the property so he can demolish it and give his own school a gateway.
- Back to the Future's Principal Strickland, this Trope's image example, has reached the zen apotheosis of this, to the point that he looks and acts exactly the same across a thirty-year timeframe. Apparently, a sufficiently single minded hate of students is the key to immortality. It runs in the family since the adventure games star his sister Edna, a stuck-up prude and Crazy Cat Lady that goes on to turn Hill Valley into a police state in another timeline.
- Dean Martin, in Back to School, does not fit this trope. However, his sympathy for Rodney Dangerfield's character is undermined by the machinations of evil department head Dr. Barbay.
- Dean Yeager in Ghostbusters (1984). This dean actually wins, and fires the paranormal researchers, forcing them to go into business as the Ghostbusters. Significantly every prediction he made turned out to be right. As it is, ghostbusting remained a wildly unregulated and un-systematic venture.
- Ms. Calley in Jennifer is the principal of an elite school that mostly caters to rich kids. She despises the titular character for her poor background, while she lets Alpha Bitch Sandra Tremayne get away with murder (her father is an influential senator who gives the school huge contributions). She even threatens other staff members with dismissal if they don't put up with Sandra's behavior.
- Dean Walcott in Patch Adams is not only a despotic bully over his medical students, but goes the extra mile by treating patients like scum as well.
- Played straight to the extent that he actually tries to discipline Patch on grounds of "excessive happiness". As the movie is at least somewhat based on a real story, arguably a case of Truth in Television.
- Mr. Gale Nolan from Dead Poets Society. This vile and Cruel man cares more about his All-Boys school's outdated traditions and his own personal success then any of his students' lives. He hates the idea of the boys thinking for themselves and planning their own lives, disobeying rules, and when one of them commits suicide and his father orders an investigation on what made it happen (while refusing to accept that his own blow-hard mentality drove his son into depression) Nolan threatens the boys with corporal punishment and fires John Keating for the crime of telling them "carpe diem".
- Principal Elliot T. Jindrake from Max Keeble's Big Move. The man desires to destroy anything that makes the school fun and pocket the money for his private enterprises. He is also highly pompous, making his public announcements in front of a part of his office he prepared to look like the Oval Office.
- Dean Phil Elias in Necessary Roughness isn't satisfied with the NCAA sanctions stripping down the football program; he's determined to do whatever he can to terminate the program outright, and comes close to succeeding. (It also doesn't help the team that the professor he's got the hots for is dating QB Paul Blake, who's about as old as he is.) Fortunately for the team — and unfortunately for Elias — the president of Texas State University is a football fan (and played by Fred Thompson, by the way), and Dean Elias gets his comeuppance after Blake calls a sideline play that results in Elias getting flattened.
President Carver Purcell: By the way, you're fired.
- Sister Aloysius, played by Meryl Streep in the film Doubt certainly counts as one. The film involves her going against a friendly and likeable priest who may or may not be molesting his alter boys, which is contrasted by her dominating and tyrannical control over the school. She is uncommonly harsh and controlling of the student body which is uniformly afraid of her. Even her own teachers are controlled very tightly and appear very nervous and uneasy around her. When another nun confronts her about this, she merely smiles, shrugs, and replies, "That's the way it is." Even the priest she's rallying against accuses her of holding the school and parish back from "Progressive education and a welcoming church" in their final speech together.
- Dean Richmond from The Nutty Professor movies qualifies along with Mean Boss, considering most of his behavior towards Sherman.
- Dean Alan Halsey of Re-Animator is initially a nice enough fellow but is corrupted by the nasty Dr. Hill into becoming a jerk. Then he's killed by zombies, re-animated and becomes even more of a nightmare to work with.
- Principal Takes A Holiday: The wayward Principal Frank Hockenberry is a strict authoritarian, and none of the students seem to be learning anything while he's in charge. This makes it more justifiable when the main character recruits a homeless man to pass himself off as the substitute principal and institute some sweeping changes.
- Dean Pritchard of Old School is like this to the protagonists because he's the younger brother of a classmate of theirs, and they all used to pick on him when they were younger ... though his behavior to the other students in the fraternity, whose only "crime" is hanging out with the protagonists, and the student body president, who didn't even do that (and in fact did exactly what he wanted) makes him just a dick rather than a sympathetic figure in any way.
- Pump Up the Volume provides us with Principal Crestwood of Hubert Humphrey High. She has institutionalized her own brand of student margination via keeping tabs of whichever students piss her off or she has decided are "losers" (which is flat-out illegal... and yes, she actually calls them that when she gives her Motive Rant) and expels them for any reason she can find so they won't taint her school with their lack of productivity. When one of the students commits suicide, she pretty much doesn't does more than the standard knee-jerk reactions expected of her and "Happy Harry Hard-On" starts broadcasting she does anything in her power to stamp down on student rebellion to the point that she doesn't even tries to make herself look justified by the end.
- Mr. Warren is the camp director version of this trope in Summer Camp Nightmare, as he hardly allows the teenage boys of Camp North Pines to have any fun, going so far as to have the rec room's TV set only receive one channel which is full of religious programming. He also ends up cancelling the co-ed dance planned with Camp South Pines over John and Stanley's obscene performance of "Beef Baloney", and further restricts any contact with the girls' camp after Chris Wade is caught making out with Heather. One of the teenagers comments that he used to be a very strict high school principal. He is accused of being a pedophile after Peter, one of the young campers, reports of some "inappropriate actions" the camp director allegedly did unto him that made him wet his pants. He ends up killed halfway through the film after the teenagers take over the camp, and his body is dumped into a cave.
- Lt. Harris in Police Academy has this role alongside with Sadist Teacher as part of a gambit to foil the Mayor's initiative to let common people became part of the police. Although technically the head of the Academy is Absent-Minded Professor Commandant Lassard. Interestingly Harris is still a pain in the ass for most of the cast in the rest of the series even after he's no longer their instructor (but still their superior).
- Stan Gable the main antagonist of the first film in the Revenge of the Nerds franchise became dean of the college in the third movie, and plays this role until his HeelFace Turn in which he "comes out of the closet" (he literally puts it that way) as a secret nerd. Averted in the first one as the dean is actually incredibly benevolent to the nerds (probably because he's a nerd himself) although he lets the Couch bully him (which makes no sense as he is his boss, but anyway...)
- Harry Potter:
- Harry Potter and the Order of the Phoenix: Dolores Umbridge takes charge, uses her blood-quill on at least two students, and allows Filch to whip students.
- Harry Potter and the Deathly Hallows, Severus Snape — who has been promoted to headmaster of Hogwarts — in some ways meets this trope, being a strict and humorless disciplinarian, though as with previous books his off-putting personality is balanced by the fact that he's actually a good person. He's secretly fighting the villains as headmaster and protecting the heroes.
- Dr. Bledsoe from Invisible Man. He expels the narrator for revealing his rough past to the school's investors, brags that he'd let every black man hang if it meant he'd keep his position (despite being black himself), and goes on a Motive Rant about how power doesn't need to prove itself.
- Agatha Trunchbull from the children's book Matilda seems to be this trope taken to its irrational extreme, as the headmistress inflicts acts of extreme and horrible violence and cruelty upon her young students, knowing their parents won't believe them. This was based on Dahl's experienced with cruel headmasters in his youth.
- Every single adult (with three exceptions) in The War Between The Pitiful Teachers And The Splendid Kids hates their students, which is unsurprising given that they all reside in a prison school for horrible teachers and smartass kids. They win(!), but not completely.
- Miss Minchin from A Little Princess enslaves Sara Crewe, whom she has always disliked, when the latter loses her fortune.
- Mr. Krupp of Captain Underpants who, due to brainwashing becomes the titular superhero whenever he hears fingers snapping. The movie reveals that he's a more sympathetic version of this as he lives alone and has nobody who cared about him. George and Harold fix his problem by hooking him up with Edith the lunch lady.
- Older Than Radio: Mr. Brocklehurst from Jane Eyre, 1847. He is not only the headmaster but the treasurer of a charity school for girls, and he appears to relish publicly humiliating the young women in his care for such horrific sins as having naturally curly hair. When his own wife and daughters troop in, however, they are shown to be elaborately dressed, complete with stylish false curls. Even worse, Brocklehurst's insistence on the lowest-quality food contributes significantly to a typhoid epidemic that kills a large portion of the student body.
- Miss Eulalie Butts, headmistress of the Discworld's Quirm College for Young Ladies in Soul Music, is a very mild example. She means well, she's just not really equipped either mentally or emotionally to deal with the likes of Susan Sto Helit, who refers to the Anthropomorphic Personification most people know as "Death" with the term "Grandfather", more or less legitimately (her mother was Death's adopted daughter, and her father was Death's apprentice). Faced with situations she doesn't understand, Miss Butts tends to fall back on The Rules, of which she has rather a lot.
- J. J. McHabe of Up the Down Staircase. Although he essentially governs the high school, his official title is Administrative Assistant. He adds the abbreviation Adm. Asst. to his signature, prompting Miss Barrett to dub him Admiral Ass.
- Katherine Brooks, principal of Queen's Academy in Anne of Avonlea. She turns out to be Sour Outside, Sad Inside and the title character manages to befriend her by the end of the film.
- Miss Bubb in Gay from China at the Chalet School. Madge Russell employs her as a temporary headmistress when Miss Annersley, Miss Wilson, Miss Edwards and Mdlle de Lachenais are all injured in a Bus Crash, and she immediately imposes her authoritarian standards on both the girls and the staff, with Madge unable to keep her in check due to her daughter Josette being ill. Things get so bad that Joey Maynard, who's come back to the school to help out, writes a letter begging Miss Wilson to come back, and Gay Lambert runs away after Miss Bubb refuses to let her see her brother-in-law before he is stationed abroad. (The book takes place during the Second World War.)
- The Automator in Skippy Dies. He's dead-set against Howard's attempts to deviate from the textbook or anything that challenges social expectations, and becomes the main antagonist in the last third of the book. He's dead-set on modernizing Seabrook but transparently and crassly only cares about money and prestige, not the well-being of students, and will cover up horrible crimes if it protects the school's image. He also is set against Skippy in particular, seeing him as a troublemaker (rather than the person in trouble that he is) due to his sometimes odd behavior and using him as a scapegoat.
- While Nero in the fifth A Series of Unfortunate Events book The Austere Academy is only the Vice-Principle of Prufrock Preparatory School, the lack of an actual principle there leaves him as the highest authority there and is probably one of the biggest Hate Sinks in the entire series. He is responsible for the abhorrent conditions of the school like the complete incompetence of his teachers, the fact that even the weekends are school days and is also the reason for the various nonsensical rules and the cruel and unusual punishments for breaking them, like the punishment for being late to lunch (in-spite of there being no set lunch hour) being that the student will have to eat with your hands tied behind their back. He hires Sunny (who is a baby) to be his secretary and has her silver-ware taken away during lunch hour because students aren't allowed in the administrative building. He is convinced that he is a musical genius and spends all of his free time (including time where he should be doing his actual job) practicing on the violin, and even then he has absolutely no talent on it, playing it with the wrong hands. He forces everyone in the entire school to attend his six-hour concerts, with anyone who is late or absent for them - regardless of the reason why - to buy him a bag of candy and watch him eat it. He seems to have an irrational hatred for orphans, responding to anything the Baudelaires words by snidely repeating it back to them like a Spoiled Brat and putting them in a rickety, uninhabitable shack because they do not have guardians to sign the right permission slips to let them live in the actual dorms.
- Spy School: The Spy School's principal is a Pointy-Haired Boss who slacks off a lot, and hates Ben for somewhat irrational reasons. The students codename for him him is "The Idiot."
- Averted with Mr. Sturgeon in the Macdonald Hall books. Even though he's nicknamed "The Fish" because of his focused gaze, he's actually a Reasonable Authority Figure. Played straight with Mr. Wizzle in The Wizzle War, an Obstructive Bureaucrat to the highest order and is an incredibly easy Hate Sink for a lot of the students.
- Principal Osgood Conklin on Our Miss Brooks. Mr. Conklin is pompous, perpetually in a bad mood, and tends to run Madison High School with an iron first. In one episode, it's revealed that he has proverbs like "Respect through Power" hung prominently throughout his office.
- Principal Snyder from Buffy the Vampire Slayer, who hates Buffy so much that when he expels her at one point (because she was framed for murder — he also lied to the cops about it) Giles has to brutalize him and intimidate him into taking her back because he was willing to refuse even orders from the Supreme Court. There is the implication that he isn't actually a teacher. And of course, he is somewhat redeemed by two things: first, the immortal line "Whoaa Summers! You drive like a SPAZZZZ", and telling the Scaled Up Mayor to get the hell off his campus.
- Vice Principal Gavin Price in Joan of Arcadia. Semi-averted in that the literal Word of God notes that Price isn't actually evil, he just doesn't understand kids.
- Parker Lewis Can't Lose of course had one of those — Grace Musso. And even she is considered better than Dr. Norman Pankow, director of the neighbouring school.
- Rowan Atkinson as the headmaster in the "Fatal Beatings" sketch, and the roll call sketch, which had use of Punny Names.
- President Bates on 15/Love was often treated as this by the students, and did have a tendency towards allowing students like Sunny, who had major financial backing, to get away with murder. That said, he was really more of a Manipulative Bastard/Stern Teacher cross, and it showed.
- Dean Borak from Boy Meets World. He was actually played by Paul Gleason, the same actor who played the above-mentioned Principal Vernon in The Breakfast Club. Best of all, Dean Borak openly admitted that he was one of these: "Make no mistake about it, boys, I am a nasty, nasty man."
- Dean Craig Pelton in Community is normally a subversion of this, usually being more of a friendly but rather inept and slightly creepy and inappropriate administrator (particularly towards Jeff), but he had a go at this trope in "Biology 101" when the surreal antics that peppered the school prompted him to grow a goatee, wear a suit and start acting as more of an authoritarian. Unfortunately, he wasn't very good at that either, and it soon collapsed when he came into conflict with the Vice-Dean of the Air Conditioning Repair annex of his school... who turned out to wield considerably more power than him.
- Mr. Gilbert from The Inbetweeners - he openly despises his students and punishes them at every opportunity with an imposing sadism.
- Principal Caplan of Mighty Morphin' Power Rangers, despite being a Reasonable Authority Figure most of the time, could be this at times. He is especially quick-tempered when the episode needs a reason for (some of) the rangers to be unable to fight. Sometimes just accidentally bumping into him could warrant a detention.
- Mr. Herkenbae from Malcolm in the Middle gets promoted to Dean of Discipline at Malcolm's high school.
- Cathy Munsch, Jamie Lee Curtis' character on Scream Queens (2015), is a female example of this. She holds a longstanding grudge against sororities, possibly stemming from an incident in her past, and she forces Kappa Kappa Tau to admit any student who wishes to pledge. Chanel, the head of KKT, is not amused in the slightest.
- Japanese drama Shōkōjo Seira has Mimura Chieko, the director of the school, who makes every living moment in Seira's life miserable. The "Bitterman" of the trope really stands out because Chieko was once classmates/friends with Seira's deceased mother and felt inferior compared to Seira's mother who was adored and kind to everyone. So she decides to take out her anger on Seira instead.
- Radio Free Roscoe: Explored with Principal Waller, whose brutal crackdowns on minor infractions are revealed to stem from a belief that by making these sorts of lesser offenses seem like a big deal he will head off greater problems in the future; he'd rather have the school's rebel element think that it's sticking it to the man by listening to RFR and toilet-papering the cafeteria than destroying school property or using drugs. He eventually loosens up and has a number of bonding moments with the main cast, most notably Travis.
- Veronica Mars has vice-principal, later principal Van Clemmons as this at first, although later in the series Clemmons is shown to actually rely on Veronica's detective abilities and even hire her to solve crimes committed against the school, becoming much friendly toward her.
- Hank Zipzer has head teacher Mr. Love, and his replacement Mr. Joy. In both instances, this a case of a Non-Indicative Name. They care about the school and the students only so far as it will enhance their own reputations. Mr. Joy even refers to the students as 'learning units' during his school announcements.
- Principal Hader from 100 Things to Do Before High School is the principal of Pootatuck Middle School. In the first episode she serves as the main antagonist, but in the rest of the series she serves as the secondary antagonist/anti-heroine. She is a very strict authority figure and usually doesn't care about others' opinions. Her nickname is 'Darth Hader'.
- 7 Yüz: Aytaç, the vice principal in "Büyük Günahlar", who seems to have it in for Mete specifically. Following a scuffle that was instigated by another student, Aytaç singles Mete out for punishment, reprimanding and slapping him in front of his peers. The incident prompts Mete to conspire against Aytaç in an act of retribution.
- Blue Mountain State: Dean Simon is a grown up Academic Alpha Bitch who resents that the popularity of the football team overshadows the university's status as an academic institution. This brings him into conflict with both the team as he tries to reign in their partying and Coach Daniels as they fight for influence over the school community.
- The video game Bully features Dr. Crabblesnitch, the head of Bullworth Academy. Indeed, Jimmy actually does end up expelled near the end. Downplayed in that Crabblesnitch isn't so much evil as merely a bit deluded and clueless about precisely what's going on in his school.
- The principal of Kindergarten's eponymous, well, kindergarten. He uses his trusty shotgun to solve pretty much any problem that comes his way, including if the problem is one of his students; gives anyone who asks about missing student Billy mind-altering pills so they won't think too hard about it; and is the one who kidnapped Billy in the first place, performing experiments on and mutating him in an attempt to make him produce the substance used for making said pills.
- Dean Harding in the original Persona fits this trope to the T. He's nicknamed as Darth Harding at times. His original nickname in Japanese is "Vice Principal Hannya." By Persona 2: Innocent Sin/Eternal Punishment, he's still a douchebag. He also made a Deal With Joker to brainwash his school's students and faculty into respecting him, and to regrow his hair.
- Donna Walker from Criminal Case: Grimsborough, the dean of Grimsborough University, is revealed to have a special hatred for the members of the school's Psi Sigma Gamma sorority, including its president Madison Springer, all of whom she classes as narcissists and opportunists who only exist to crush others and be congratulated for it; in Madison's case, Ms. Walker gave her multiple notices for sneaking out of the dorm at night. As it turns out, Ms. Walker's hatred stems from an incident in her past, back when she was a student at the universityshe was the victim of hazing by the members of the sorority at the time, which consisted of forcing her to drink excessive amounts of alcohol that resulted in her being in a coma for four days. What especially angered her was that the dean at the time did nothing to punish the sorority members for the incident.
- In Dubbelmoral!, an early '90s Macintosh game based on the quadrennial Lundakarnevalen festival at Lund University in Sweden(hence the Swedish game dialogue), the University's Rector Magnificus does not take kindly to being puked on by drunken students such as the Player Character. If this happens three times, he expels the PC from the University as a Non Standard Game Over.
- Liberal Art Played with, in that the unnamed Dean only yells at other administrators.
- chainsawsuit's "Boner College" strips feature a Dean Bitterman by the name of "Dean Flaccid".
- The Inexplicable Adventures of Bob! has Dean Martin (no relation) of the Science Department at Generictown University. His Berserk Button is when people ask him how Jerry Lewis is doing.
- The headmaster in Gunnerkrigg Court seems to be this. Given the nature of the comic, he may be playing at some deeper manipulation, but he mostly seems to exist to oppose Antimony enjoying herself while being too impotent to actually do it.
- No Future has Mr. Lassiter. He is judgemental, lacks compassion, and while he is too professional to indulge in wanton sadism, he is petty enough to give detention for pointing out his son fits the Troubled Teen bill better than Andrew does. He also calls Andrew a mistake to his face, sending him running out of his office.
- In The Saga of Tuck we meet the high school's Principal Nickerson, who thinks a suicide attempt is no reason to skip class and assigns detention accordingly.
- From the Whateley Universe, we have Amelia Hartford, who — despite not having the central administrative position — still influences quite a few student affairs, trying to get some of the protagonists expelled, and clearly giving the Alphas preferential treatment. A genuine smile from her managed to seriously creep out her student assistant. And she seems to be in a 'vice principal' position at Whateley Academy.
- The Professor Garfield site intro (which no longer plays automatically, but can still be found here) features a short, angry man whose nametag (which can be briefly seen) reads "Dean B."
- Dean Vernon from Futurama episodes "Mars University" and "A Clone of My Own" is a parody of the trope and borrows liberally from Dean Wormer. "Robot Hooooooooouuuuuuusssee!"
- The Simpsons
Dean: Hi there! Hello, I'm Dean Peterson, but you can call me Bobby. I just want you to know if you ever feel stressed out from studying or whatever, I'm always up for some hackey sack. Or, hey! If you just want to come by and jam, I used to be the bass player for the Pretenders.
- "Homer Goes To College" (1993) provides the trope namer in the Show Within a Show School of Hard Knockers. An excerpt portrays a prank pulled on Dean Bitterman by two brothers of the wacky Chugalug House. When Homer attends Springfield University, he assumes (or wishes) its laid-back Dean Peterson, who is a complete subversion, to be his nemesis:
Homer: I can't wait to take some of the starch out of that stuffed shirt...
- A decade later, in "I'm Spelling As Fast As I Can" (2003), Homer meets George Plimpton. He clearly hasn't learned his lesson.
Plimpton: Hello, I'm George Plimpton, founder of the Paris Review. I also played the evil dean in Boner Academy.
Homer: You monster! Why did you expel Boogerman!?
Plimpton: He replaced my tennis racket with a rubber phallus.
Homer: Heh-heh! That was awesome!
- Principal Seymour Skinner, of Springfield Elementary, can be one of these in his less sympathetic moments.
- Homer's high school principal, Mr. Dondelinger, was even moreso. Though this is a somewhat Justified Trope as the students he punishes are slackers and miscreants.
- Skinner has his own Dean Bitterman in Superintendent Chalmers.
- After Skinner is fired from his job in "Sweet Seymour Skinner's Baadasssss Song", an intense, large, and angry man named Leopold ominously states that things are going to be different around the school...before cheerfully announcing that it's because Ned Flanders is going to be taking over. He appears again in "The PTA Disbands" with a similar gag - this time introducing Marge Simpson as the teacher for Bart's classroom.
- Professor Rotwood, upon being promoted to Principal Rotwood, used his position shamelessly to torment title character American Dragon: Jake Long. He was also the victim of pranks by the mundane student body, so...
- Rotwood is sort of in the same brotherhood as Crocker from Fairly OddParents, so really, it's only to be expected that no one really respects him, and that he'd go a little power-mad.
- The Gromble qualifies this fully in Aaahh!!! Real Monsters, he's the headmaster of the monster academy. He still is shown as a fair teacher though... in that he Hates Everyone Equally.
- Mr. Lamar Bone from Doug, "One second late and it goes on your permanent record!" He had his sympathetic moments though, it was suggested that his attitude came from being overworked because the actual principal never did anything.
- Principal Wartz of PS 118 from Hey Arnold!: He's the strict, yet open-hearted principal of the school. In the end of episode "Sid's Revenge" he gave Sid detention for bringing a bar of soap to school.
- Whatever Happened to... Robot Jones?: Principal Madman rules Polyneux Middle School with an iron fist, and it's just Robot's luck that he's also a raving technophobe.
- Headmaster Grimm from Ever After High. It's implied he imprisoned his own brother in a secret library underneath the school because he threatened to defeat the purpose of his school. He's also way more sympathetic to the Royals, the school's "Rich Kids" for all intents and purposes.
- He's not without reasons, though: breaking away from the plot too much causes the characters to cease to exist. Or do they?
- Principal Prickly from Recess (although he does have his good moments, especially in the movie).
- Daria: Principal Ms. Angela Li of Lawndale High School. She also is a Politically Correct Villain and Professional Butt-Kisser — witness the time she enters Daria's art (without her consent) into a contest, modified so it won't be about raising awareness of bulimia and instead is about a generic pretty girl (which is why Daria didn't consent) and tries to get Daria expelled when she defaces her own art (Daria's mom threatened to sue Li once she had the whole picture).
- Glenn Ponzi from Dude, That's My Ghost! is this to Spencer, he enjoys making his life miserable, he tries repeatedly to get him kicked out of the school, until he figures out if he did he'd have no one to torment.
- The principal of the adorable animal school in Over the Garden Wall gets mad when he sees them playing and having fun due to Wirt and Gregory's intervention. Although he turns out to be a nice guy at the end.
- X-Men: Evolution had Principal Edward Kelly, taking over as Principal of Bayville High from the second season onwards. Overall he was more restrictive than Ms. Darkholme (Mystique), but once mutants were eventually exposed to exist he became a full-blown case of Tyrant Takes the Helm, using every resource he had available as principal to turn the lives of all mutant students on his campus into a living hell (treating them as second-class, destroying all of their achievements through accusing them of "cheating" with their mutant powers, looking the other way when Bully Brutality happened) out of Fantastic Racism.
- Headmistress Crone from Gravedale High was in charge of the titular school and often had a stern and ill-tempered demeanor.
- Prinical Skeeves from Star vs. the Forces of Evil is mean, rude, only cares about money not to mention a complete bully to Star.