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Enemies with Death

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Some heroes are Pals with Jesus, while the least fortunate are Enemies With Death.
For some reason The Grim Reaper, or an Anthropomorphic Personification of some other concept intrinsic to existence, takes a serious dislike to our hero and has it in for her/him. Maybe the hero has upset their Evil Plan, they dislike her/him for doing things counter to their nature (like saving lives, cheating death, or becoming immortal), or they have a boss who orders them to antagonize the hero.
Oddly (especially when it's Death) he/she/it won't just kill the protagonist with a snap of the fingers. There may or may not be some form of cosmic rulebook obliging Death not to outright kill the hero, or it may be merely a Psychopomp with no power to directly cause people to die, but likely it's an authorial fiat to give the hero a chance to survive. Death has two ways to make the hero's life difficult: fight the hero physically (usually as a Boss Battle), or mess with the people and events around the hero, making the her/him either a Weirdness Magnet or a Doom Magnet chased by the Butterfly of Doom. If Death is particularly gentlemanly, it could offer to resolve the whole thing with a nice game of chess. If instead Death is a right bastard, it may well do "nothing" to the hero.
Interestingly, when our hero kills Death (they're a hero armed with a Save Point, they'll succeed eventually) it is not a case of Immortality Immorality, and it won't result in Death Takes a Holiday. Usually. It may have something to do with the fact that an actively malicious Death is somehow going AWOL and not doing its "duties" with impartiality. Or, the hero may discover too late that You Kill It, You Bought It. Or perhaps Death just can't be killed permanently.
Contrast Monster Roommate and, more specifically, Don't Fear The Reaper.
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In the Iron Druid Chronicles the protagonist has the inverse problem. A female goddess of Death of his religion is rather fond of him and likes to use him for sex. This has given him a form of immortality but has also made him a mortal enemy of one of the gods of Love. Since in that pantheon all the gods are very nasty, vengeful and quite barbaric, the difference is mostly academic. The god has tried to make the protagonist's life miserable for two millenia and is always looking for a way to kill the protagonist.
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Harry Potter and the Deathly Hallows has a fable that takes this form: three brothers use magic to cheat death, and Death himself shows up to "congratulate" them with three gifts. Two of the brothers die soon after because they chose or used their gifts poorly, just as Death hoped, but the third uses his gift to hide from Death, and decades later, as an old man, he decides he's lived long enough and passes the gift down to his son. It's suggested that this gift is Harry's invisibility cloak and that Death has poorer eyesight than a cat.
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After The Mighty Thor severely ticked off Hela (Norse goddess of the dead) one time, she cursed Thor to be undying, but to have extremely brittle bones, leaving him in constant pain and held together by an improvised suit of armor and splints. (Obviously, he got better.)
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Sluggy Freelance: Inverted at first, when it's Bun-bun the mini-lop who has it in for an Anthropomorphic Personification; he tries to kill Santa Claus every Christmas due to a grudge whose origin he can't remember properly. Eventually he pushes Santa so far that he snaps and starts plotting Bun-bun's death too. As this theme progresses, other Anthropomorphic Personifications of the holidays also become Bun-bun's enemies (others, cowed allies), although they'd rather just leave him alone after he shows he could beat up just about any of them.
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Death is usually a pretty nice guy, or neutrally doing his job, but in the first book, before his characterisation was quite settled, he could be slightly malevolent, and annoyed that he couldn't tell when Rincewind was going to die. He stopped actively going after Rincewind as early as the second book, and took the view of I'll get him eventually. I get everyone, eventually.
Death's attitude toward Rincewind (and fellow death defier Vimes) softens significantly in the later books, to the point where he sees them as a curiosity (or a source of mild exasperation at worst) more than anything else. At one point, while Vimes is in a particularly dangerous situation, Death appears off to the side sitting in a chair and idly flipping through a book. When Vimes notices him, Death says something along the lines of Oh, don't mind me. I'm just waiting to see how this turns out.
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Mortality: Watson out-right refuses to let Death take his friend. Seriously. He's NOT letting Death kill his friend. You know who it is. And who wants to bet Death is thinking Oh, Crap! when he has to deal with Watson?
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The Auditors of Reality, on the other hand, who are roughly personifications of the laws of the universe, are antagonistic towards all life, especially intelligent beings. They have it in for Death, too, particularly as he takes the side of life against them; this results, especially in Reaper Man where he's a protagonist, in the odd situation that Death is "Enemies with Death".
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Bruce Coville's Book of... Ghosts: Alex in Not From Detroit, who chases down and fights Death to get his wife's soul back. In the end though, while he successfully gets Margie's soul back, he can't stop Death from taking her for good, and the two settle their differences, Alex choosing to let Death take him early so he won't have to outlive his wife.
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In Odin Sphere, several of the characters have to fight Odette, the Lady of Death, for various reasons. Gwendolyn succeeds in killing her. This wound up being something of a mistake, since it winds up being one of several events that help trigger the apocalypse, killing all but four people on the planet.
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The Outer Limits (1995): In the episode "White Light Fever", Harlan Hawkes is a billionaire centenarian with an abject fear of death due to his extremely traumatic childhood experiences, and uses his wealth to reserve revolutionary medical treatments for himself. The Grim Reaper concludes that he's outstayed his welcome, and starts to hunt Hawkes Final Destination-style.
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Alpha Flight foe Deadly Ernest was a WWI soldier who rejected Death when she came to claim him on the battlefield. He later discovered that by rejecting her he had been cursed to never die and to bring death to anyone who touched him.
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SCP-1440 is a man who won immortality from the grim reapers at cards. The reapers take revenge by destroying everything human-related wherever he goes.
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This is used at least four times in Supernatural.
The demon Alastair uses Death's scythe to kill two Reapers, part of a ritual to break one of the 66 seals on Lucifer's cage. He's stopped by the Winchesters from killing Tessa and completing the ritual though.
In the later part of season 5, Dean hunts down Death so he can kill him and take his ring. When he finally meets the Grim Reaper, it turns out that things don't work that way in the Supernatural universe.
In the first episode of season 7, Castiel and Death get into a very heated argument, in which Castiel outright threatens to kill Death. Death isn't impressed by the "mutated angel".
Billie has never liked the Winchesters but grudgingly accepts working with them after she becomes the new Death. When their deal to kill Chuck falls apart she's more than ever determined to reap Dean. Of course, she failed to mention that she was planning on becoming the new God all along, starting with killing off everybody the Winchesters have saved from Apocalypse World. Castiel foils her by dragging her with him to the Empty.
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Discworld:
Death is usually a pretty nice guy, or neutrally doing his job, but in the first book, before his characterisation was quite settled, he could be slightly malevolent, and annoyed that he couldn't tell when Rincewind was going to die. He stopped actively going after Rincewind as early as the second book, and took the view of I'll get him eventually. I get everyone, eventually.
Death's attitude toward Rincewind (and fellow death defier Vimes) softens significantly in the later books, to the point where he sees them as a curiosity (or a source of mild exasperation at worst) more than anything else. At one point, while Vimes is in a particularly dangerous situation, Death appears off to the side sitting in a chair and idly flipping through a book. When Vimes notices him, Death says something along the lines of Oh, don't mind me. I'm just waiting to see how this turns out.
The Auditors of Reality, on the other hand, who are roughly personifications of the laws of the universe, are antagonistic towards all life, especially intelligent beings. They have it in for Death, too, particularly as he takes the side of life against them; this results, especially in Reaper Man where he's a protagonist, in the odd situation that Death is "Enemies with Death".
In Hogfather, Mr. Teatime devises plans for killing Death, as well as seemingly every other anthropomorphic personification on Discworld, in his spare time. He nearly pulls off the one against the Hogfather (a Santa Claus expy) until Death and his daughter Susan get involved.
One wizard thought to escape Death by getting into a box adorned with every protective enchantment he can think of. Once he's inside...
Turns out there wasn't much room for, say, airholes...
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Hood does, however, have a beef with the T'lan Imass as a whole, as is revealed in The Crippled God, who are a race that collectively cheated death by becoming undead. For a long time, he could do nothing about it, but then the T'lan Imass decided to make Dassem Ultor their champion, and since such motions have metaphysical investiture in the series, all Hood had to do was to serve him the information the T'lan Imass had just made him the God of Tragedy on a hot platter. It's never explicitly explained what truly happened, but Onos T'oolan claims that Dassem and his daughter were actually Hood's weapons directed at the T'lan Imass.
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Fallout Tactics has this as a potential character trait for Ghouls. They gain access to perks faster than regular ghouls, but they have a chance of taking damage for no reason other than DEATH!!!
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A significant theme in Persona 3. And ultimately, all you can do is hold Death off for a time - the battle is not truly winnable. In a less existential sense, The Grim Reaper will hunt you down and (unless your levels are significantly stacked) wipe the floor with you if you dawdle too long in Tartarus.
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The Series 8 finale of Red Dwarf, "Only the Good...", has Rimmer escape from Death by hitting him with a Groin Attack. Made even funnier if you flash back to Series I, when Lister picked up a length of pipe to ward off his inevitable demise:
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Happens in Touhou Youyoumu ~ Perfect Cherry Blossom when you fight Yuyuko, a super-powered ghost whose main power is inflicting death upon others. Said battle happens in the local equivalent of an afterlife. A more literal use of this trope is during Touhou Kaeidzuka ~ Phantasmagoria of Flower View when you must fight Komachi to get her back to work, so it's your character who deliberately makes Death your enemy.
What is important to remember is Komachi is just a ferryman shinigami who takes the spirits over to meet the Yama, not a reaper shinigami who comes to collect the person when their time is up. However, Tenshi the Celestial is immortal through the fact she has defeated every reaper shinigami who has come for her, which makes the fight against her in Komachi's storyline a Moment of Awesome.
Hermits are also on probation from Hell for their immortality, and have to perform good deeds or get taken by a shinigami. Hermits who don't, like Seiga, have to fight off or escape the servants of Hell to survive. The same applies to Celestials.
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The Lion King Adventures depicts Death as the Big Bad of Series 3, and Simba marks his ability to defeat him as one of his greatest achievements.
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Castlevania (2017) — just like in the video games, ends up featuring Death as an antagonist, arriving in the very climax of the final season, turning out to be the series' Greater-Scope Villain responsible for much of the bloodshed throughout the series, being the Final Boss behind Dracula himself.
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In The Tiger's Wife, by Téa Obreht, the narrator's grandfather tells of his encounters with the "deathless man," who angered Death — his uncle — by saving a woman who was meant to die, and was punished with immortality.
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At the end of the Neopets War of the Obelisk plot, the Awakened, an army of the undead, are pitted against Death. They fear him because he is a threat to their immortality. It also would appear that he is the little brother of the leaders of the Awakened, Lanie and Lillie. As they encourage the dead to rise from their graves, and he wants the dead to stay dead, they are at odds with each other.
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In Dante's Inferno, the protagonist Dante is assassinated. When Death appears before him and tells him that he will be damned for his sins, Dante gets up, takes the knife from his back, and fights Death. Dante won. But not before stealing Death's scythe and killing him with it.
And then it turns out Death never came for him in the first place as a tangible being. He just keeled over on the spot.
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The titular character of Elisabeth has a love-hate relationship with Death. She doesn't fear him and continually rebuffs his advances (romantic or otherwise) throughout the show, until her Despair Event Horizon (at which he refuses to take her because he realized in that moment she wanted to use him as an escape). In the German version, Lucheni implies that Death goes out of his way to mess Sisi's life up out of spite.
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Inverted in Universe X. Death is under siege by Captain Mar-Vell's army, and fights back, but it seems she'd be perfectly willing to leave him alone if he'd return the favor. And then it turns out that the world needs a Death.
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In Puss in Boots: The Last Wish, Puss’s greatest adversary ends up being The Grim Reaper himself in the form of the Wolf, who he's been unknowingly pissing off for years due to arrogantly wasting the extra lives he gets as a cat and claiming himself an immortal legend who "laughs in the face of death" — thus, Death decided to test that notion and take his last life personally. This conflict ends amicably, however; Puss shows Death he's undergone Character Development and humbly accepts his mortality, the latter in turn giving into his honor and sparing Puss, wishing him well with his life until they inevitably meet again.
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Chakan: The Forever Man is based on this. A Swordsman brags so much about his skills that he declares not even Death could better him. Death accepted the challenge with a condition: If Chakan could defeat him, he'd be granted eternal life. If Chakan was defeated, he'd become Death's eternal servant. Chakan wins, but turns out he was Blessed with Suck since he cannot rest until all Evil is eliminated.
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In the original Shadow Hearts, the God of Death embodied as Fox Face doggedly hunts Yuri through half the game, apparently having a major grudge against him that is never spelled out, beyond wanting to help the monsters killed by Yuri take their revenge. Implied to be one of the innumerable lesser death gods as common in Japanese mythology, as opposed to the ultimate personification of Death as in Western mythology.
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Journey to Chaos: By the time of Transcending Limitations, Eric Watley has offended three grim reapers and all of them want to kill him. Their boss, Lord Death, forbid it until one of them used their Final Wish to kill him. Eric would have died right then and there if not for other deities intercepting their attacks.
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The Lexx crew are personal foes of an Affably Evil Manipulative Bastard incarnation of Death.
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In Hogfather, Mr. Teatime devises plans for killing Death, as well as seemingly every other anthropomorphic personification on Discworld, in his spare time. He nearly pulls off the one against the Hogfather (a Santa Claus expy) until Death and his daughter Susan get involved.
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Hood himself is the God of Death because, as is hinted at in Toll the Hounds, then confirmed in the prequel trilogy, he at one point decided to fight the very concept of Death itself and called together a huge army to do so. Technically, they lost, but in best You Kill It, You Bought It fashion, Hood who was mortal up until that point became the God of Death.
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In Dragon's Crown, one of the bosses you fight is the Death God, who will chase your party of adventurers through the Castle of the Dead until you successfully send it back to the underworld or escape via an area filled with sunlight. The Flavor Text of the Angel of Destiny Treasure Art explains that death gods only started appearing in the world after people gained the powers of resurrection from the gods, causing people who are supposed to have died to not show up in the afterlife. Considering how often adventurers use that specific gift from the gods, it probably explains why the death gods aren't in good terms with them.
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The Fire God Agni from Kubera fights the god of death just to save Brillith.
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Yu-Gi-Oh! GX has an episode where the opponent's trading card is actually The Grim Reaper himself. Other cards based on Death have also appeared, such as Reaper of the Cards.
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Skips in Regular Show. Also arguably the whole group as of "Skips Strikes," since Rigby won a bet against Death and defeated Death's bowling team.
Another borderline example is in "It's Time" where Father Time is shown to be frustrated with Mordecai for microwaving his clocks and decides to free him from eternal imprisonment only because he accidentally trashed Father Time's living room.
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The Final Destination films have the main cast fight Death in the form of a faceless Butterfly of Doom that's out to get them for not dying when they should have. Except it is revealed (or retconned) in the fourth movie that the characters DID die when and how they were supposed to- the visions that saved them from dying were sent by Death itself! Suck on that, causality!
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Twisted Metal 2's Mr. Grimm is in fact the Grimm Reaper. He's pretty weak but has the single most powerful projectile in the game. His reason for entering the tournament is to make people die faster to feed his hunger for souls. He gets his wish. For a while. When global war breaks out, its only so long until everyones dead and there's no more deaths, ever again.
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Malazan Book of the Fallen:
Dassem Ultor, a legendary Malazan general started out as the Champion of Hood, the God of Death, but felt betrayed by his god when his beloved daughter died under suspicious circumstances which looked a lot like Hood using her for his own purposes. Dassem declared himself an enemy of his former patron and spends most of the series pursuing a way to kill Hood. Hood himself really does not have any strong feelings on the matter.
Hood does, however, have a beef with the T'lan Imass as a whole, as is revealed in The Crippled God, who are a race that collectively cheated death by becoming undead. For a long time, he could do nothing about it, but then the T'lan Imass decided to make Dassem Ultor their champion, and since such motions have metaphysical investiture in the series, all Hood had to do was to serve him the information the T'lan Imass had just made him the God of Tragedy on a hot platter. It's never explicitly explained what truly happened, but Onos T'oolan claims that Dassem and his daughter were actually Hood's weapons directed at the T'lan Imass.
Hood himself is the God of Death because, as is hinted at in Toll the Hounds, then confirmed in the prequel trilogy, he at one point decided to fight the very concept of Death itself and called together a huge army to do so. Technically, they lost, but in best You Kill It, You Bought It fashion, Hood who was mortal up until that point became the God of Death.
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Zeus: Master of Olympus: This trope and its opposite are equally possible depending on whether Hades is set to be enemy or friendly. If an enemy, he unleashes Cerberus on you, or shows up and instakills every walker in the city along with cursing your silver mines. But if friendly (and you built him a sanctuary), he'll send Cerberus to defend your city, bless your silver mine production (not to mention his sanctuary providing silver veins to mine), and defends your city against other gods (and there's only two gods more powerful than him).
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In the Fafhrd and the Gray Mouser stories the Death of their world is something like a cosmic bureaucrat that answers to some vague pan-dimensional forces. He has to meet particular quotas of who dies within allocated time periods (measured in mortal heartbeats) and is only really allowed to do so by manipulating natural events. He can't snap his fingers and kill somebody unless they have a severe medical condition, but he can make sure that they might have a nasty incident with some badly maintained masonry. The exceptions to this rule are the main characters, who once attempted to steal his mask; since then he's had it in for them and has resorted to toying with reality by teleporting crazed berserkers into their living quarters.
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In God of War: Ghost of Sparta Thanatos is the Big Bad Death somehow gets killed, even though he is Death incarcerate. Its implied Kratos has absorbed his power and become the new death, but since this is an Interquel its unknown if he lost this status in the beginning of God Of War 2.
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This is the origin of Mr. Immortal's power.
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Pathologic has an odd version of this. One of the main characters is a Bachelor of Medicine who honestly believes that the very concept of "death" is not a natural part of our existence, but rather another disease we have simply yet to cure. Some of the NPC's even refer to death as his natural enemy, which is true on more than one level given his profession.
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Although the Queen of Maggots in The Cat Lady is, by her own admission, not truly "death", she may as well be given her ability to resurrect the dead and prevent souls from passing on into the afterlife. The game provides an excellent example of what happens when you annoy Death: she picks a recently-deceased soul, resurrects them, and makes them functionally immortal while telling them that the only way they get out of their crapsack life is by murdering the hell out of you.
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Shuma Gorath and the other Many-Angled Ones alter reality in the dimensions they take root in to remove Death so that life will grow out of control and become cancerous, spawning more Eldritch Abominations like themselves. And even Death itself (as in the cosmic anthropomorphic personification of death) can't permanently kill them.
Marvel's Cancerverse is the living result of one of these alterations through an in-universe Deal Withthe Devil. It took A multi-versal invasion, bringing in other Eldritch Abominations, and a moment of stupidity on part of Thanos to bring Death back, and even then it's temporary since Death's gone again.
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One Season 1 episode of Big Wolf on Campus had Death decide to claim Tommy's life, when he had his work interrupted by the latter wanting to save an old man from him. It takes a lot of convincing for Death to leave Tommy alone, although he later returns in a Season 2 Clip Show episode to claim Merton's life instead.
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In Diaries of a Madman, Navarone turns out to be Discord's Arch-Enemy. Discord being the Anthropomorphic Personification of chaos/discord.
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By the time of Darkest Dungeon II, the Flagellant has attracted the ire of Death herself thanks to his constant self-abuse, to the point he’s little more than a walking corpse that tainted his Blood Magic thanks to his body rotting away, and he outright fights her off as death would put an end to his suffering. Thus, any party with him in it has a chance for Death to spawn in at the end of a Resistance encounter to try and claim him and any other poor sods in your party.
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When Deadpool and Death become infatuated with one another after Deadpool has a number of near-death experiences, a jealous Thanos prevents Deadpool from dying and joining the entity.
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Saint Seiya has the heroes fight Hades, god of the underworld... and his minion gods Thanatos and Hypnos, gods of death and sleep, respectively. Just how powerful they are or how wisely they use their abilities is debatable, as they both physically fight the saints (and lose) rather than kill them by natural causes or make them comatose, respectively.
Hades actually uses his powers intelligently and gives a Deal with the Devil to dead Gold Saints. It just happens that the Gold Saints took the bait to accomplish more strategic objectives, but this is still a valid tactic specific to a Death God.
In Hypnos' defense, his special move does make the target go into an endless sleep, with the caveat that it has No Ontological Inertia once he is beaten. Thanatos, on the other hand, may just be an arrogant Jerkass who prefers toying with his opponents rather than plain killing them.
Thanatos tries to use the insta-death on a non-fighter, Seiya's long lost sister, but the lowest ranked saints manage to block it (at great damage). It's implied that the nearly godly main characters would be immune, what with divine blood protection.
It should be noted it worked on former minion Pandora who just betrayed them, giving Phoenix Ikki a key to go to Elysion.
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Castlevania (Franchise)
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