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{{trope}}
{{quote|''"Somebody's sucked all of the life out of these kids, and unless TV has lied to me, it was a crusty, bitter old Dean!"''
|'''Homer Simpson''', ''[[The Simpsons (animation)|The Simpsons]]''}}
A [[Sadist Teacher]] in charge of an entire educational institution. This guy hates the protagonist and his friends 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.
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In terms of rank, the [[Authority Tropes]] arguably at the next step down are [[Badass Preacher]], [[Corrupt Corporate Executive]], [[Irish Priest]], [[Landlord]], [[Preacher Man]], [[Pedophile Priest]], [[Schoolteachers]], [[Sinister Minister]], and [[The Vicar]]. For the next step up, see [[Majorly Awesome]].
{{examples}}▼
▲{{examples}}
== Anime
* Similar to ''[[A Little Princess]]'', Japanese drama ''[[Shokojo Sera]]'' 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.
== Fan Works ==
* ''[https://archiveofourown.org/works/31492754/chapters/77903009 Mars Attacks: Simpsons]'' has a retired drill sergeant replacing Skinner as prinicpal and becomes this.
== Film ==
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* Dean Alan Halsey of ''The 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 Frank Hockenberry in ''[[Principal Takes A Holiday]]'' is portrayed as evil for trying to keep a student named John Scaduto in line. Yes, his school wasn't as fun as Fitz's, but a school's primary purpose is education, not fun. Of course, this is semi-justified in that nobody was learning while Hockenberry was in charge. Scaduto is portrayed as justified in doing things that are downright illegal (like hiring an actor to impersonate a principal).
* Donna Weller in ''[[
== Literature ==
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== Western Animation ==
* Dean Vernon in ''[[Futurama]]'' ("''Robot Hooooooooouuuuuuusssee''!")
* Trope name comes from [[Show Within a Show]] "School of Hard Knockers" featured in the ''[[The Simpsons (animation)|Simpsons]]'' episode "Homer Goes To College" (1993), excerpting 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 [[Reasonable Authority Figure|Dean Peterson]], who is a complete subversion, to be his nemesis:
{{quote|'''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''':I can't wait to take some of the starch out of that stuffed shirt... }}
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* 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.
* Dean Toadblatt in the ''[[The Grim Adventures of Billy
* The Gromble qualifies this fully in ''[[Aaahh Real Monsters]]'', he's the headmaster of the monster academy.
* Mr. Lamar Bone from ''[[Doug]]'', "One second late and it goes on your ''permanent'' record!"
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