Wardens are Evil
Regardless of what the rest of the guards are like, the warden will always be evil.
A character gets sent to the slammer. He or she might fear or dread several aspects of the incarceration, including lack of freedom, abuse by other prisoners/guards, and bad food. But none of those are the scariest thing about the prison. Nope, it's the warden. The prison's warden will be a heartless, soulless monster dedicated to abusing and bullying prisoners in the most brutal ways possible. Alternatively, he or she will torment prisoners emotionally by saying hurtful words and putting them down. Or it could be both. Bonus points if his or her actions are illegal themselves. Double bonus points if he/she gets busted and becomes an inmate in the prison they once ruled with an iron fist. Don't even think about thinking about crossing him or her, and don't even think about thinking about escaping. If you do, the punishment will make you wish you were dead (assuming it doesn't involve death). Note that this doesn't necessarily have to be a prison warden; it could just be the commander of a prison-like institution. Compare Corrupt Politician, Screw the Rules, I Make Them! Contrast Reasonable Authority Figure.
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Anime and Manga
- One Piece: While he really means well for the world, Chief Warden of Impel Down Magellan qualifies. He has stated (and demonstrated) that he has the authority to punish or kill any prisoner there as he sees fit, and along with being a Poisonous Person, it's the reason he's so feared there. He's not without limits, though; his former colleague Shiliew is far worse, brutally massacring the prisoners for the fun of it. This disgusted Magellan so much that he ordered Shiliew to be imprisoned.
- Batman and the Outsiders #4: Warden Brewster of Gotham State Prison deliberately denies a prisoner (codenamed "Meltdown") needed medical treatments and then lies that the Prison Board was responsible. He does this to trick the dangerously radioactive felon into escaping so he can be killed to save the public. Turns out the warden has decided rehabilitation doesn't work, so he's been finding ways to "legally" off prisoners.
- In Escape from Alcatraz, the contrast between the unnamed Warden and the rest of his staff is quite obvious. The guards and the Deputy Warden are just people doing their job and don't resort to plain brutality at any point. The Warden on the other hand is a cold, vain bully. He drives an old prisoner to madness by taking his painting privileges away just because he didn't like a painting the man made of him. His mission to ensure that Frank Morris will remain in prison is also portrayed as more of a personal obsession than just fulfilling his duties as head of the prison.
- Cool Hand Luke. The Captain is the sadistic warden of a chain gang prison. He ruthlessly mistreats the title character by locking him in a punishment box and having him beaten.
- In The Shawshank Redemption the warden is skimming money off of the price he charges for prisoners to work for various buinesses/public works/etc. When Andy reveals the corruption the warden commits suicide.
- Death Race: Warden Hennessey of Terminal Island Prison is a cold-hearted bitch which shanghais Jensen Ames (in more ways than one) into taking part of the titular Deadly Game (and plans to either keep him racing forever or kill him as soon as his usefulness as the season's Frankenstein is over-not that she had a plan to have anybody win). The Prequel movies also retroactively show that she had some amount of Small Name, Big Ego-she says on the first movie that she was the creator of Death Race, but in reality it was the corporation she works for, and they knew she would take credit around anybody who could buy it.
- The Last Castle: James Gandolfini 's Warden Winter is an excessively brutal, excessively petty bastard. Doling out rules about prisoners not being able to act like soldiers anymore? OK, tough, but understandable. Using a number of brutal methods to break prisoners' wills (especially when Determinator Badass General Eugene Irwin arrives), and ordering prison guards to shoot prisoners in the head with 12-gauge rubber bullets (which is highly lethal) if they somehow manage to piss him off (which is unfortunately often)? Firmly cements him in this trope.
- In The Count of Monte Cristo, the warden of the Chateau d'If is a sadist who among other things has the prisoners flogged and given a lash for every year of imprisonment. Incidentally, this is a case of Adaptational Villainy, since in the novel the guards (the warden doesn't appear) are presented as good men doing a bad job.
- An interesting case in Discworld. The Ankh-Morpork City Watch is generally portrayed as heroic, but the city prison, the Tanty, is apparently answerable to the Patrician rather than the Commander of the Watch. When the protagonist of Making Money is springing a prisoner, he is pleased to find Bellyster, an evil cuss who doesn't even have the grace to turn his back when gobbing in a prisoner's food, on duty, because of the problems he's about to make for the man.
- Holes: The warden at Camp Green Lake crosses the Moral Event Horizon when she slashes Mr. Sir across the face with her rattlesnake-venom-polished nails. Later, it is revealed that she established Camp Green Lake for the sole purpose of using inmate labor to find the relics of outlaw "Kissin' Kate" Barlow.
- Al Capone Does My Shirts: Warden Williams is a tyrant who threatens to fire Moose's father just because Moose said something rude. A slight subversion in that his victims aren't prisoners, though.
Live Action TV
- In Red Dwarf VIII, when the crew are back on the Dwarf as it was, but are sent to the onboard prison for correction: the Warden is a sadistic grudge-holding bully who takes delight in having Rimmer beaten up.
- Basic Dungeons & Dragons module DA1 Adventures in Blackmoor. The warden of the Prison Out Of Time is a sadistic former slave master who has been ordered to kill King Uther rather than let him be rescued. He carries out this order by trying to magically torture the King to death.
- Classic Traveller Adventure 8 Prison Planet. The warden is a lying, hypocritical crook who orders cruel punishments for minor offenses, violates prisoners' rights in order to make his quotas and takes out his anger at his superiors on prisoners by arbitrarily denying parole.
- Avatar: The Last Airbender
- The warden in the episode "The Boiling Rock" would rather die (and have prisoners killed as well) than tarnish his prison's record of zero escapes. Also, he tortures a prisoner into revealing escape plans.
- The warden in "Imprisoned", voiced by George Takei, is a Bad Boss who throws subordinates overboard, delights in crushing the spirits of those in his custody, and on top of it all is a Dirty Coward.
- Walker from Danny Phantom is an obsessive Rules Lawyer when it comes to the rules of The Ghost Zone, and will go to great length to belittle his prisoners and keep them under control by any means necessary. His prisoners are ghost, but he can ensure a Fate Worse than Death.
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