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Gluttons can't eat or drink in Hell because they ate and drank so much in life. And they are trapped in putrid soil because they produced nothing but garbage in life. And they are being torn apart constantly by Cerberus's three sets of bloody teeth, because Dante is one sick motherfucker.
— Lore Sjoberg, The Book of Ratings, Dante's Inferno Punishments, Part 1

Black Mage: (Upon dying and going to hell) Wait, if I did evil, and you guys are evil, then shouldn't be showering me with rewards and concubines?
The Devil: This is hell. We're big on irony here.

Most depictions of Hell involve some form of eternal punishment for the damned souls who are sent there. In Ironic Hell, they get a more personal service. Each sinner gets a punishment that is an ironic reminder of the sins of which he or she is guilty. A glutton might be force-fed something unpleasant for eternity, or might be prevented from eating ever again.

Many examples of Ironic Hell are references to Dante's Inferno (Book 1 of the Divine Comedy), which depicts Hell in this way. It was published in 1314; however, the basic idea goes back even further, to Greek legends of Tartarus.

It may be worth noting that, despite Dante's work being mainly a sociopolitical statement and not supposed to be taken as a literal journey through the afterlife, people still presumed that he knew what he was talking about and have used his often sanctimonious depictions of Hell, what acts are sinful, and how sinful they are, taken directly from his writings.

Often coupled with Self Inflicted Hell.
Examples:

Mythology and Religion
  • One good Tartarus example: Tantalus, who fed the gods his own chopped-up son for dinner, was chained to a rock and cursed with unending hunger and thirst; a bunch of grapes hung just above his head, and he stood in waist-deep water, but whenever he tried to reach for these, they would move out of his grasp. (From this, we get the word "tantalizing".)
    • Another one that always stayed with this troper: Sisyphus was the trickiest Greek, so much so that several times he managed to trick the incarnation of death and/or the gods of the Underworld to avoid dying. When finally taken off to the Underworld for good, he was given a task he couldn't trick or think his way out of: to roll a heavy boulder uphill every day. And at the end of every single day, when he'd finally managed to do it, the boulder would roll back downhill and he'd have to start all over again. The gods might as well have just said "Okay smart guy, try thinking your way out of this one!" (In case you're wondering why Sisyphus doesn't just stop trying to do the impossible, it's stated that his hubris prevents him from admitting defeat.)
  • After the events of 9/11 it became well known that Osama bin Laden promised paradise to the matyrs and that one of their rewards would be 40 eternal virgins. This immediatly gets picked up as an ironic form of hell, since there would be fourty extreamly beautiful women tantizing you and yet you couldn't have sex with them lest they loose their virginity.
  • A religious parable of unknown origin has the protagonist shown a vision of Hell in which everyone is eternally seated at a table filled with delicious-smelling food. However, none of them can eat a bite because they can't bend their elbows (or, in another version, their forks are far too long to reach their mouths). The protagonist then sees a vision of Heaven where the same banquet and same anatomical (or cutlery) restrictions apply, but everyone is feasting happily. Why? Because unlike the people in Hell who think only of themselves, the people in Heaven feed each other. (Depending on your sensibilities, this is either a Crowning Moment Of Heartwarming or a Tastes Like Diabetes Golden Moment.)

Live Action TV
  • The Twilight Zone episode "A Nice Place to Visit" used this trope. Rocky, an armed robber, is shot and killed by a policeman; upon recovering awareness, he is accompanied by a "guardian angel," Pip, who gives him anything he asks for. Money, women, success at gambling are all his for the taking. After a while, Rocky grows bored of perfection and the lack of any challenge in his afterlife, and asks to be sent to "the other place," whereby Pip responds that "this is the other place."
    • And another Twilight Zone example features a food critic who revels in the cruelty of his reviews. He makes short work of a Chinese restaurant. They invite him back for another meal to hopefully change his mind. Once he starts eating, he finds himself insatiable. At which point he is presented a fortune cookie which reads: You Are In Hell, and he realizes that perpetual starvation and being served Chinese food only is his damnation punishment.
    • Night Gallery did a short skit where a hippie-type (memorably played by John Astin) arrives in Hell, eager to experience the flames. The devil instead seals him in a room which is sort of a horrific cross between a 50's malt shop and a backwoods country store circa 1910. As he departs, the devil idly comments that there is a room just like it up in Heaven.

Western Animation
  • In the fourth Halloween special of The Simpsons, Homer spends a day in Hell. In the Ironic Punishment Department, Homer is force-fed "all the doughnuts in the world", but much to the annoyance and confusion of the demon torturing him, Homer enjoys the experience.
  • Futurama's famous "Robot Hell" musical sequence from the episode "Hell is Other Robots" featured Bender going through several instances of this trope for the various sins he'd committed. For example:
    Robot Devil: (singing) Cigars are evil, you won't miss 'em.
    We'll find ways to simulate that smell;
    What a sorry fella,
    Rolled up and smoked like a panatella,
    Here on Level One of Robot Hell!

Literature
  • A humorous example from the Discworld books is the punishment given to the villain Mr. Pin near the end of The Truth. After exposure to a "dark light" camera leaves him with the feeling that the ghosts of everyone he's killed are after him (long story), Pin is is told by his more sympathetic partner, Mr. Tulip, that wearing a potato to the next life will allow for reincarnation (another long story) instead of eternal punishment. Thus, when both are in a dire situation, Pin kills Tulip and takes his potato for extra protection. Appropriately, when he meets with Death, Pin is reincarnated as a potato. For the final kicker, he had killed his friend because, quote, "I wasn't meant to fry"... and the farmer who grew the potato he came back is talked by the protagonists, William de Worde and Sacharissa Cripslock, to make chips out of it. Tulip is also reincarnated, despite his potatolessness, as a woodworm, living an idyllic life in an antique desk.
    • The Discworld novel Eric also played with this one. Hell has recently come under new management, so the traditional punishments get scrapped in favor of mind-numbing eternal boredom. The Sisyphus stand-in has to read a book on the correct manner of rolling rocks up hills, for example. A book consisting of at least 10,000 tomes. Even the demon carrying out the punishment feels sorry for him; in fact, the majority of demons eventually conspire to move the current ruler of Hell into a powerless job because they're sick of inflicting the new punishments.
    • And Death seems to have even more ironic views on reincarnation. In might have been Maskerade, a rat catcher is killed, and discovers that he is due to be reincarnated - as a rat. He doesn't even believe in reincarnation, but it's made clear that reincarnation believes in him.
  • An example found in poetry that refers to a a real-life person, the first verse of Vachel Lindsay's The Congo: A Study of the Negro Race (it's exactly what it sounds like) contains the line, "Listen to the yell of Leopold's ghost, / Burning in hell for his hand-maimed host. / Hear how the demons cackle and yell / Cutting his hands off down in hell." Leopold II, King of Belgium, was the colonizer of the Congo whose occupation and forced labor amounted to a massacre of the natives of that area. Among his laws was that his soldiers had to present a [black] human hand for every bullet they fired as proof of an "enemy" killed. Because it can take more than one bullet to kill a man, somehow it evolved that chopping off a bystander's hand to save one's own skin was preferable to wasting a bullet.

Webcomics
  • The furry webcomic Jack, which is set in both heaven and hell (along with the living world), features this trope prominently. In its Hell, the people who end there are given punishments reminiscent of the way they lived or died, and are often denied memories from their past, making their ironic punishments even more cruel. The titular character is, at the same time, The Grim Reaper and the Anthropomorphic Personification of Rage with Laser Guided Amnesia, whose job, tag and amnesia are all punishment for his former sins from when he was alive. In fact, all the malevolent Anthropomorphic Personifications became that way as a result of their acts and are punished in a way symbolic of the sin(s) they personify; save for the protagonist, they all prefer to see The Punishment as more like a Cursed With Awesome, even if it obviously does not work that way.
    • That's technically untrue. The only one of the Sins who didn't seem to realize that their situation sucked was Victor (Greed, Although, Dr. Kain, AKA Envy, seems to not be able to care less either way.), and that's probably because hell's punishment for him kinda gives him what he wanted in the first place, and just him knowing he has it is enough to make him happy, even if he can't enjoy it. It's just that Jack is the most angst ridden about it.
  • Dresden Codak has a two-part piece in which it is revealed that there is a "secular Heaven", which as its name states is a secular humanist idyll populated by people who refuse to believe in the anthropomorphic deity running the place. Meanwhile, "religious Hell" is populated primarily by fundamentalists of all faiths; when a character notes it makes no sense, the comment is made that God is powered by irony.
  • Dunno the book, but this editor's dad has described a story where a murderer gets sent to a planet where he is required to kill five people per day. (Can't recall the ending: Either he grows to hate the act of killing and is thus "cured," or he finds out that they're robots and runs around killing even more of them.)
    • In the short story (not book), when he finds out they are soulless robots who can be no more murdered than a toaster, he becomes convinced all members of that alien species are robots and goes around killing them the way another man might crush an empty can of soda. The alien society's police rely entirely on a telepathic device, ignoring all witness testimony in favor of the device's reading, and each time they use the device to ask the man whether he murdered anyone, he answers defensively his genuine belief that he has not "murdered" anyone (only broken people he has been mindscrewed to believe are mere robots), so they keep having to let him free to kill again.

Video Games
  • A particularly undeserved example of this happens in Disgaea when it is revealed that Laharl's mother committed suicide to save his life. Instead of being rewarded for her sacrifice, the Powers That Be saw fit that she should serve several hundred years as a slave to the very boy she tried to save, who became emotionally stunted and violent after her death. Truly she is Blessed With Suck.
  • In Afterlife, Hell has structures which condemn people for their most usual of the Seven Deadly Sins. Most are ironic - for example, the Luxury ones remove any sex from the lives of the damned, and the Gluttony ones punish them with eating, from Taco Inferno (even the beverage is hot) to Bahb's All-U-Must-Eat (eat until you explode). The Fluffy Cloud Heaven equivalents reward them for the virtues (i.e. the Humble become famous).
  • In the Overlord expansion pack Raising Hell, you encounter some of the Fallen Heroes and their minions you defeated in the course of the regular game in the Abyss levels, suffering appropriate punishments. For example, the gluttonous and greedy halflings are trapped in a world where the pumpkins fight back and sheep explode, while their leader Melvin Underbelly is forced to repeatedly stuff himself until he explodes; the slothful Oberon is forced to watch a dreadful play detailing the fall of the elves; the womanizing Sir William is trapped in Lady Land; and the greedy dwarf Goldo is trapped in a gold statue while still conscious.

Film
  • One example of a combined Ironic Hell and Self Inflicted Hell is in What Dreams May Come, clearly based on Dante. The protagonist's wife committed suicide, and reflecting the selfish nature of the act, she is essentially trapped in a state of depression, unable to connect with others.

Radio
  • The radio series Old Harrys Game loves this trope, ranging from the Estate Agents Pit ("well, not so much a pit as a bijou basement property with unrealised potential") to the Enclosure of Eternally Pregnant Popes. Satan considers his own position to be an Ironic Punishment, and a particularly unfair one at that.

Anime
  • In Basilisk, that's what happens to Lady Ofuku in the end. After manipulating Oboro and the Iga Tsubagakure (as the leader of the Takechiyo faction they defended) in a good part of their trials, she was struck REAL hard when Oboro chose to kill herself - half to spare Gennosuke, half to get back at Ofuku and completely destroying her plans. She has a huge Villain Breakdown after that, and when Hanzou Hattori the Third finds out that Gennosuke has staged the rest to make sure Oboro is proclaimed as the winner before joining her in death, he decides to NOT tell Ofuku for a while, as punishment for her manipulations.
  • In Vampire Princess Miyu, the spiritualist Himiko Se believes the aforementioned Miyu preys on all of humankind, so she vows to hunt her down. However, at the end of the 4th OAV, Himiko is shocked to discover that she herself is at least part vampire, since she and Miyu exchanged blood when Himiko was a little girl and Miyu had just been appointed as The Guardian. Yikes, Himiko definitely Didnt See That Coming.

Fan Fiction
  • In the Good Omens fanfic Its Own Place, the angel Aziraphale's personal Hell turns out to be Heaven. The real kicker is that he doesn't even realize he's actually on Hell's torture roster because its version of Heaven is exactly as he remembers it, and he expected to be lonely and miserable there after the End (because Crowley isn't there Heaven is mind-numbingly boring compared to Earth), which makes this overlap with Self Inflicted Hell.