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The Problem with Fighting Death

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...Is that even when you win, you'll still eventually lose.
As nemeses go, you can do worse than be Enemies with Death. The Grim Reaper isn't unbeatable, he can be whipped into submission by a sufficiently cunning Guile Hero with The Plan or a sufficiently tough Action Hero with a good enough weapon or a nice game of Chess.
There's just one small problem: these cosmic entities usually play a pretty important role in the universe and afterlife. Beating them to a pulp just means you've pissed off the guy who's in charge of your eternal reward. He may decide to punt you into Hell instead of Heaven, or simply trap you in an unnatural state between life and death when it would be your time to "die." Even Immortality is no guarantee of safety, because Death will make sure the hero regrets eternal life one way or another. Heck, Death may even levy immortality as the punishment!
Killing or imprisoning Death might not offer protection either, as his sister Entropy goes around making everyone grow old and wish to die while Death Takes a Holiday or cause a plague of ghosts as the souls of the dead get stuck on Earth.
This is the problem with fighting Death, Hades, The Devil, Psychopomps, Anthropomorphic Personifications or even God; you just can't win. However, a draw may be possible with creativity. If all that matters is that there be a Death, then replacing him with someone friendlier or someone with whom deals can be struck and honored can be a way to go. This can be done by appealing to someone higher on the divinity ladder, getting someone else to kill and replace Death (or doing so yourself, if you're willing to accept the job for the rest of eternity), and flying out of Hell are all possibilities. In this way, one can say Living Forever Is Awesome.
This is rarely mentioned in stories, which can become a rather horrific revelation for viewers on a walk to the fridge as they realize that their beloved hero will eventually die and be at the mercy of their enemy. If it is dealt with in the story, it makes a fight that much more heroic, since the hero knows that winning means he's condemning himself to an afterlife of pain. Having the character face the consequences makes it a case of Broke Your Arm Punching Out Cthulhu.
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In Dark Alleys (Tabletop Game)
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Mort picks a fight with Death towards the end of the book. Death briefly tries to trick Mort into winning conventionally by killing him, which would force Mort to bear the burden of being Death in turn, but Mort refuses to take the bait.
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The Mighty Thor:
Thor, after invading Hel to rescue the souls Hela had stolen, she, as the goddess of death and decay, cursed him to never die or heal. While this actually saved his life when he battled the Midgard Serpent, a fight fated to end in a Mutual Kill, he eventually sent a Magitek robot called the Destroyer into Hel to make her lift the curse and restore him. By this point his bones had been reduced to mush and he was unable to move without assistance.
Earlier as well, Hela came to claim Thor's soul for some reason and Odin killed her dead. This was earlier when Odin and his kind were still Marvel's "only" Gods, and all things on Earth stopped dying, like plants overgrowing, gnats turning into swarms, etc.
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Harbinger (Finmonster): Danny Fenton's ancestor got into a chess game with Death, and played to a draw, which was equivalent to a win because Death had other stuff to do. So he and his wife were allowed to live out a normal life. The only problem was that because this turned Allister into a Paradox Person, this meant that he and his descendent were roped into Death's need to defend the living from an incoming Demonic invasion.
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The Colour of Magic has a clairvoyant see her death happening in a matter of hours/days from a fire, so she gets the hell out of town and takes up a mountainside residence. She dies in a landslide the moment her house goes up in flames.
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In Reaper Man, Death is given mandatory retirement, and the whole book is about the issues that ensues. An excess of life and souls charges up the world, causing poltergeist activity and objects to come to life, notably a sentient mall that tries to draw in people as consumption, metaphorically..
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Odin Sphere: Oswald the Black Swordsman must repeatedly fight off the Halja since his foster father Melvin sold Oswald's soul to the Queen of the Netherworld Odette in order to empower Oswald's Belderiver. While the Belderiver gives Oswald the power to drive away the Halja, he must also never let go of it or else the messengers of death will be on him like butter on toast, which happens twice over the story. There's also the tiny problem that utilizing the Belderiver's true power too much will eventually devour his soul and turn him into a monster and does happen in one of the bad endings. Luckily for Oswald, his wife Gwendolyn invades the Netherworld and up and kills Odette to take him back the second time around, and in the true ending the Belderiver is destroyed and freeing him from its curse. He still has a normal lifespan, but now he doesn't have to worry about any Fate Worse than Death.
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Subverted with The Flash. He found a safe way to foil Death (at least the entity who fills that role on Apokolips): outrunning him. He was actually faster, proven when the hero outran the Reaper to a child he was intent on claiming and rescued him.
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RWBY: The short fable "The Girl in the Tower" is about a woman who was rescued from a tower by a brave knight and they lived happily ever after... until, inevitably, he died. The woman petitioned the gods for help, but after they denied her and she tricked them, they cursed her with Complete Immortality until she learned to accept death. She instead used this immortality to convince an army to follow her, who attacked the gods. The gods responded by wiping out all of humanity except for the woman, telling her, once again, she needs to learn to accept death. Then it turns out the story is based on the life of Salem and Ozma.
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Sqid religion in Freefall holds that every Sqid's first theft is from the god of life, who then eternally pursues them to get it back.
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The SCP Foundation has quite a few examples, but SCP-1440 is in a league of its own: a reluctantly immortal man who has wandered the world for an unknown length of time because his presence destroys everything associated with humanity.
Although according to the author, his mistake wasn't winning, it was taunting death after he won.
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This is a very prominent recurring theme in Supernatural, sometimes literally involving Death himself. By the fifth season and later the Winchesters have made enemies out of both Angels and Demons, who control much of the afterlife — Heaven and Hell respectively of course. Since this is a show where Death is Cheap and characters have come back from the dead multiple times, the real concern isn't about actually dying, but what happens afterwards. If Sam and Dean weren't required as Angelic vessels, they would just be tortured in the afterlife for all eternity considering all the havoc they have caused to both factions. They even manage to get Death annoyed at their constant resurrections, and he implies this trope to them when they try to bind him.
In season 5's "Dark Side of the Moon", Sam and Dean enter Heaven (as Ash tells them, it's hardly the first time either, but the Angels keep wiping their memories) after they are killed by another pair of hunters. The high-ranking Angel Zachariah eventually captures them and immediately begins torturing the two. Because they humiliated him by escaping his clutches several times on Earth, he promises that he's "gonna be the Angel on your shoulder for the rest of eternity".
In season 5's "Two Minutes to Midnight", Dean tries to kill Death to stop the Archangel Lucifer, unaware that he could've gotten what he wanted without killing him, as they both had a common interest in stopping the "bratty child". Dean assumes that Death would be angry at this, but it turns out the problem with a human fighting Death is that the human just doesn't matter.
In season 6's "Appointment in Samarra", Dean gambles with Death to get Sam's soul back from Lucifer's Cage and return it to his body with a temporary fix to keep the hell memories from killing him or worse. Death buys him a hotdog and holds up his end of the bargain—even though Dean failed his—because Dean learned something. Death of course continues to impress upon Dean the depths of his insignificance at every opportunity. It's here that Death also clarifies that he himself cannot, in fact, die.
In the season 7 premiere, this trope is almost actually achieved when Dean, Sam, and Bobby use a spell to bind Death so they can politely ask him to kill Castiel before the mutated angel gets even more destructive, explodes and takes the world with him, or worse. Dean attempts to placate Death with fried pickle chips, but you can tell by their expressions throughout the affair that they expect him to lay the smackdown on them whether it works or not. It doesn't. Except Death does give them an extra eclipse so they can try to fix Castiel's overpoweredness. Death doesn't seem to hold a grudge (probably because they're too insignificant), but he warns them not to try that again. When you're Death you don't need to hold your grudges, they all come back to you eventually.
In season 8's "Taxi Driver", Bobby Singer gets to find out what the result is of pissing off someone who has a say over the afterlife allotted to mortals, in this case the King of Hell by undermining his plans and killing his demons on a regular basis. After he dies again after having been a ghost, Crowley instructs a Rogue Reaper to take his soul to Hell so he can have him tortured forever. Crowley intervenes again when the Winchesters try to release Bobby's soul to Heaven instead, but Bobby is saved by intervention from the Angel leader Naomi, who's a tad higher on the cosmic scale.
However, Death conveys to Sam in season 9's "I Think I'm Gonna Like It Here" that it would be an honor to reap him when he faces his death willingly, because of all the persistent self-sacrifice and good they've done despite being only humans. He considers Sam one of the rare beings he has come across that he would both take an interest in judging and find worthy of praise.
In the Season 10 finale, they actually manage to kill Death, using his own scythe. However, all the other Reapers are quite pissed that somebody killed their boss, not to mention that they're sick of the two of them dying and being resurrected so often. A Reaper named Billie tells Sam that the next time they die will be the last time, and their souls will be sent to "the Empty" where resurrection is impossible.
Even Castiel, an angel who can freely wander into Heaven, gets hit with this after he dies and goes to The Nothing After Death. He inadvertently wakes up the Shadow, the primordial Eldritch Abomination which resides there, and develops a deep enmity for Castiel as it really doesn't enjoy being awake. When Castiel initiates his own near-death to go back, the Shadow tortures him until he resurrects.
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Discworld:
Death doesn't get annoyed about people "cheating" him, because he doesn't see it as a contest. In his own words, he can be robbed but never denied. That said, The Colour of Magic has him get a bit pissed off over Rincewind's entirely accidental avoidance of their appointments. But that was the first book in the series, and it's worth noting that he takes up the above view throughout the course of the story; from regularly trying to collect Rincewind's soul whenever mortal peril strikes, he eventually settles for just waiting to see whether he gets to escape or not.
Played straight in a few stories though:
The Colour of Magic has a clairvoyant see her death happening in a matter of hours/days from a fire, so she gets the hell out of town and takes up a mountainside residence. She dies in a landslide the moment her house goes up in flames.
Mort picks a fight with Death towards the end of the book. Death briefly tries to trick Mort into winning conventionally by killing him, which would force Mort to bear the burden of being Death in turn, but Mort refuses to take the bait.
Sourcery has, in its prologue, Death come to claim an old wizard named Ipslore the Red. Ipslore attempts to avoid his fate by having his spirit possess a wizard's staff and giving it to his Reality Warper son. Death doesn't seem to get mad, but agrees to let Ipslore continue "living" if they agree on a catch that lets Death claim Ipslore's soul eventually: Ipslore concedes that he will go quietly when his son willingly gives up the staff (something a wizard would never do).
In Maskerade Granny Weatherwax cheats him at cards to save a child. Death, by then has come to admire this aspect of humanity, and lets her win.
In Reaper Man, Death is given mandatory retirement, and the whole book is about the issues that ensues. An excess of life and souls charges up the world, causing poltergeist activity and objects to come to life, notably a sentient mall that tries to draw in people as consumption, metaphorically..
Soul Music, Death stops working. However, his granddaughter Susan is available as a necessary (but eventually unwilling) replacement.
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In the World of Warcraft universe, defying Bwonsamdi, the Loa of Graves, is not a good idea, as you'll need literal immortality to escape his wrath. Zalazane learned that the hard way when he tried to mess with the Darkspear dead.
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In Maskerade Granny Weatherwax cheats him at cards to save a child. Death, by then has come to admire this aspect of humanity, and lets her win.
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Black Bart and Captain Blood from Pirate101 discover that that Death does not like it when people try to prevent him from claiming souls. Once the player makes it possible for him to claim these two, Death's voice makes it clear that he's enjoying claiming their souls.
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In the backstory of Soul Nomad & the World Eaters, Lord Median The Conqueror killed Master of Death Vigilance to save his son from a wasting disease. He also believed that by killing death, he would never die and be able to continue the reign of prosperity that he had brought to Haephnes. Not only did his son die anyway, but killing Vigilance ended up completely wrecking the circle of reincarnation and allowed Gamma to steal all the souls Vigilance would normally be responsible for, it caused Vigilance's partner Virtious to kill Median in retaliation, and finally Gamma ended up poaching Vigilance's soul and his boss reincarnated him into Psycho for Hire Gig and sent him back to his own world to hurry along the collection, as it were. Nice job, Median.
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Xena: Warrior Princess:
In one episode, King Sisyphus captures Celesta (aka Death) in order to prevent his own death. This results in there being no death ever (for example, those who are terminally ill or fatally injured are still kept alive even if they happen to be on the brink of death at the time... oh, and a crazed bandit who Xena dealt a fatal injury to ends up becoming undead and persuing her), and, should Celesta herself die (which will happen if she remains restrained for too long), then it will be permanent.
Much later in the series, Xena attempts this herself to obtain immortality for herself and her loved ones when they end up on the Olympians' hitlist. It's a ploy to obtain Celesta's tears which can place people in a state of temporary death. Xena had intended to fake her and Gabrielle's deaths to throw the Olympians off their trail. Unfortunately, Ares was also fooled and took their bodies to a secluded location out of grief. As a result, Xena and Gabrielle were revived much later than they had planned.
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Defied in Castlevania: Lament of Innocence. After whipping Death into submission, Leon basically states that "Death" is only a psychopomp (which is why he could), and that as a good, God-fearing Christian, he'll be going to Heaven anyway in the end, so it doesn't matter. This is especially significant if you consider Mathias's conviction that God Is Evil and attempts to make Leon feel similarly— Leon is betting his immortal soul on the exact opposite being true, even after everything that's happened to him. There is no shaking this man's faith.
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In Death and the Maiden, actually dying requires you to look Death in the face and call him by name (though any name, including nicknames or epithets, will do). Avoid this, and you won't die... but that doesn't mean you can live peacefully afterwards. Those who avoid dying at their allotted times get hit with increasingly bad luck to make up for the extra life.
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An endgame reveal in Persona 3 is that the being that is prophesized to bring about the Fall is Nyx, the incarnation of the concept of death, or rather the being that introduced it to Earth long ago. All the Major Arcana Shadows fought throughout the game are fragments of Death's Avatar, and by killing them the protagonists have accelerated its arrival. It's stated by Ryoji, himself a fragment of Death, that Nyx cannot be destroyed or defeated no matter how strong the protagonists are due to representing the very concept of inevitable death. He turns out to be completely correct: when Nyx is fought as the final boss, you're merely fighting an Avatar - and you don't even get to destroy that, it simply flies away after the fight and the real Nyx appears, a being of incomprehensible magnitude that gets the entire party on their knees just by existing. The world is only saved by the protagonist awakening the Universe arcana and sacrificing his soul to become the Great Seal. It also helps that Nyx as an entity appears to be completely without malice and doesn't mind being put back to sleep.
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In Saint Seiya: The Lost Canvas this is actually explicitly referenced. At one point one of the Gold Saints (while living) is teleported into Hades (the location) and notices that all of his dead friends are trapped in the ice of the ninth circle, cursed to this punishment for having opposed Hades. It backfires since their souls help the Gold Saint beat the crap out of his opponent by powering him up. This ultimately gives him enough determination to decide to end things once and for all with Hades, when the next war comes around.
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Exalted: In the distant past, the gods and the Exalted rebelled against the Primordials that had made the world, overthrew them, and killed several of their number. However, the cycle of life and death was not meant to process the souls of Primordials, and they thus lingered as tormented, undying souls that can only die by dragging the world to Oblivion; killing any more was clearly not an option. A solution is imprisoning them instead. It's not a lasting solution.
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Dungeons & Dragons has the Binder class, which allows a character to borrow the power of unfortunate entities left homeless in the afterlife. These include:
A master thief who was also a devout worshipper of Olidammara, god of thieves and pranksters, who stole his own soul back from his god via a deathbed repentance. Olidammara was (sincerely) touched by this final act of devotion, but also left with a problem. If he acknowledged it as a truly epic prank, he would claim the avatar's soul and render the prank meaningless. If not, he would lose the soul of one of his greatest devotees, who would. Eventually, he decided the only way to properly repay him was by granting him demigod status. In limbo.
A powerful mage who almost became a god. Key word:almost. Understandably, this tends to burn a few bridges along the way.
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Harry Potter: The story of the three brothers from Harry Potter and the Deathly Hallows (and The Tales of Beedle the Bard) uses this. Three brothers use magic to cross a dangerous river without dying, much to the annoyance of Death. The anthropomorphic personification pretends to congratulate them, and offers them each any prize they want. The first asks for an unbeatable wand. It works, but when the he boasts too much about it, someone slits his throat while he's sleeping. The second asks for a stone that lets him see the dead. He uses it to call upon the spirit of his fiancee, who passed away shortly before their marriage. However, she's only a shadow, and he finds himself pining after someone he can never have, so he commits suicide to join her. The last one, though, is smart enough to recognize that Death may have an ulterior motive, so he asks for something that will prevent Death from finding him after they part — and Death grudgingly gives him the cloak off his back, the very one he uses when he invisibly collects the dead. Then, when he judges that his time has come, he gives the cloak to his child and willingly goes with Death as an equal.
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Averted in Castlevania (2017): Trevor mentions that Death is not The Grim Reaper (although he did inspire the concept in the popular imagination), but rather a primordial elemental spirit that feeds on the energy of death. Therefore, he can be fought and even destroyed without completely upsetting the natural order.
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In Yesterday Upon The Stair, murderers tend to have the ghosts of their victims hanging around them. They can't do anything while their murderer is still alive, but they know that eventually the person will die and they can enact their revenge. This is what happens to All for One's doctor, at the hands of the victims of the Noumu project, and is what will happen to All for One himself if he doesn't choose to move on with his brother once he truly dies.
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Antagonists of the Felix Castor series will often make elaborate plans for war against the dead. When confronted with these plans, Felix will point out that, if it comes to war, the living are screwed because of this trope.
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"The Soldier And Death": The soldier trapping Death in a magical bag resulted in nobody being able to die — the suffering of the wounded was extended, and the old just became more and more tired and infirm... eventually, hearing the cries of the people, he released Death from the bag, expecting to become his first victim — but Death was frightened by the soldier, and fled from him before resuming his duties. Since neither Hell nor Heaven will take him in, the soldier wanders still, hoping for the day he will be forgiven and allowed to rest at last.
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In the Final Destination series, people can escape their fate through premonitions, but Death, who seems to be a mean-spirited Sentient Cosmic Force, immediately starts to chase them down to balance its books. You can't run. You can't hide. Sooner or later, Death will find you.
Clear is the only one on Death's list to have survived a meaningful length of time beyond her intended end. In 2, Kimberly goes to her for advice, only to learn that Clear hasn't really cheated Death, merely had herself institutionalized to protect herself. Under the circumstances, nothing short of destroying the entire building would be able to kill her, and Death isn't so overt. Once she leaves the building, Death gets her in short order.
A major conceit of the series is that Death follows certain rules which make it possible to give yourself a clean slate, but trying to use those rules is like playing a stacked game. Death has supreme latitude over how to get at those who escape its wrath, with even those who thwart it finding out how long it can play its game. Figure out its order and avert the next death? It just skips to the next one on the list and then cheats by looping over again and again. Kill someone to take their remaining years for yourself? Death gets what it wants regardless, and you may have well just bought yourself a few days. Actually reset your place in Death's design? It can just break its own rules by setting up another gruesome accident down the line to get you. The fourth film even shows Death gives people those premonitions in the first place so it has people to hunt. The game is entirely rigged.
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Destiny 2: Xivu Arath, the Hive god of war, grows stronger whenever a battle is fought in her name. It doesn't matter whether they're fought for her or against her. Season of the Seraph hinges on reactivating humanity's Kill Sat network in order to deal her armies a crushing blow — only for it to be revealed that such a slaughter, even against her own forces, would act as a Summoning Ritual to bring her here immediately. Season of the Witch attempts Cutting the Knot on the problem of fighting war, with Eris Morn bootstrapping herself into the bootleg Hive god of vengeance in order to contest Xivu Arath's monopoly on violence.
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In The Thanos Imperative, the Marvel Universe is invaded by an alternate universe where death was destroyed and life grew unchecked throughout the universe to the point where life itself has become an Eldritch Abomination, governed by "The Many-Angled Ones."
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Explicitly dealt with in Earth X's sequel Paradise X. After Captain Marvel kills Death, the old and sick start piling up. They resort to recruiting Jude the Entropic Man to dematerialize those who seek the relief of death, going on to the Paradise Mar-Vell constructed.
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Happens to Jack in Fables for about a page or so. During the Civil War. Results in Technically-Living Zombie. Actually a subversion. Jack manages to trap Death and is later forced to release him when the consequences are made apparent. Death, however, was quite thankful because it was the first day off he'd ever had.
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Puss in Boots: The Last Wish: Puss has lost eight of his nine lives due to his recklessness. He has one chance to fix this: track down the Wishing Star and wish for new lives. But throughout his journey, he's stalked by a bloodthirsty wolf bounty hunter that wants him dead. The wolf turns out to be The Grim Reaper himself, furious at how Puss wasted his lives while laughing at death, and has decided to take Puss's final life in retribution. In their final fight, Puss acknowledges he could never defeat Death, but has grown to value his life and the people he loves. Death departs, with Puss acknowledging they'll meet again.
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In Chakan: The Forever Man, the main character has this problem. Chakan is a master swordsman, who defeats all comers. Eventually, he boasts that he could beat Death himself. Death is not amused and takes him up on this challenge. Chakan summarily beats Death like a slave, causing Death to concede, and grant Chakan's wish for immortality, but neglecting to do anything about physical aging...
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Journey to Chaos: Reapers are a fact of reality. Defeating them is unthinkable for most mortals and even if you do they'll just respawn in the Abyss and come after you again. Even if you somehow permanently kill them, that will just put you on their boss's shit list.
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Death Note: Light hits this problem from two directions in his quest to use the Note to rule over the world as God. First, no matter how clever he is, he remains mortal, and will eventually die of old age if nothing else. Second, he has the shinigami Ryuk looking over his shoulder at all times. Ryuk says in the beginning, and he reminds Light more than once, that he will kill Light the moment he stops being interesting. When Light backs himself into a corner and begs Ryuk for help, Ryuk immediately kills him. The irony is that Light refused multiple times to take the Shinigami Eyes because they would cut his lifespan in half, but he was outlived by several people who took the Eyes (including Misa, who took them twice).
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Superman storyline "The Black Ring": "The Soldier And Death", Lex Luthor was injured grievously enough to allow him to see and speak to Death. When he invokes the elephant in the room, she comments that, while resurrection is technically a possibility, to a Time Abyss on her league, it ultimately amounts to a rounding error and it's no skin off her nose. And hey, at least the zombies are having fun!
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Discussed and later inverted near the end of Xenoblade Chronicles 1. The party is holding one last strategic meeting to decide what to do now that Zanza has awakened and started cleansing the Bionis of life. Alvis brings up the point that even if the remaining peoples of Bionis could hold out against Zanza's direct attacks indefinitely (which is itself highly unlikely), Zanza could simply feed on them as they die of natural causes, making a war of attrition a losing strategy even in the best case scenario. The party eventually decides to take Zanza head on, as not fighting him at that point would only lead to him becoming stronger.
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On the other hand, Death in Castlevania 64 directly states his intent to admit Reinhardt to hell. Judging by Reinhardt's ability to invoke God's forgiveness, though, it's unclear if the threat is valid.
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In Dante's Inferno this is seemingly averted as Dante kills the Grim Reaper in the prologue and steals his scythe with no repercussions afterwards. This is because it was actually a Dying Dream. Dante didn't really fight Death — he's just another damned soul in Hell being manipulated by Satan for his own purposes. The scythe itself crumbles away once Dante realizes the truth.
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Pathologic: The Marble Nest has the personification of Death taunting the Bachelor for failing to contain the plague, dressed as an Executor. As the Bachelor's assistants are also dressed as Executors due to the heavy clothing making a good barrier versus infection, it takes him a while to realize precisely who is speaking. Not that it matters, as everything is a dying hallucination of where everything went wrong. Death even gives the Bachelor a chance to repeat the day, but the results will be the same.
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Touhou Project: Spell Card duels are intended in part to prevent the Problem. Not only do they serve as a Power Limiter for immensely powerful beings who could otherwise squash any opposition with a snap of their fingers, but they are also nonlethal, which means that there is no risk of causing The End of the World as We Know It by killing someone vital to the continuation of existence. Interestingly, Reimu (one of the main characters of the series) is among those, because without her the barrier that keeps Gensokyo separate from the main world would collapse.
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In the backstory of Malazan Book of the Fallen, a whole Jaghut race waged literal war with Death, with armies and all. End result was one of them assuming a mantle of God of Death as Hood.
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Emperor Sun Hai of the Jade Empire, along with his brothers, decided to go off and mess with (read: kill) the Water Dragon - trapping the spirits of the dead in the world of the living where they quickly went insane and started massacring people. By the time the game ends, Sun Hai is dead and the Water Dragon is back in charge of the afterlife unless the Spirit Monk takes over for her or allows Sun Li to rule. One may expect Sun Hai, now one of many spirits subject to judgment, to have learned a lesson on not interfering in the affairs of the Celestial Bureaucracy.
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The Magnus Archives, "Cheating Death": A mortally wounded soldier cheated at a game of chance with Death. When the soldier won, he was promptly Stripped to the Bone while the skeletal "Death" in front of him regrew its flesh, and returned to its previous human form. The soldier, now a new "Death" was cursed with supernatural luck as he wandered the world playing games to regain his humanity.
Zig-zagged in that the soldier did eventually manage to lose a game after about two centuries. He's still not truly human though, with a Healing Factor, an inability to eat or sleep, and a persistent craving for ''something''. He has decided however, that this existence was worth it though, since "a living hell is, after all, still living." And then he, or at least another like him, shows up in a later statement after changing his mind and trying to commit suicide, only to learn that he can't kill himself. Even after blowing off most of his head.
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The otherwise four-colour superhero game Freedom City has a surprisingly bleak mention of this. The superhero Daedalus is immortal, and not happy about it. However, the reason he's never seriously tried to kill himself is specifically because his archenemy is Hades, Lord Of The Underworld. However much immortality sucks, spending eternity in the realm of a god who hates you and has total power over you would be much worse.
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God of War III has Villain Protagonist Kratos killing most of the Greek pantheon, including Poseidon, Hades, Hermes, Hera, Helios, Hephestus, and Zeus. The result? Horrible floods, plagues, plants dying, the sky blackened by storms and the dead unable to find their resting place. Oops.
In God of War: Ghost of Sparta the Big Bad is the Death God himself, Thanatos. But this trope is ultimately averted. Death somehow gets killed, even though he is Death incarnate. Its implied Kratos has absorbed his power and become the new death, but since the game is an Interquel it's unknown if he lost this status in the beginning of God of War II.
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Subverted in Red Sonja when meets Death in a fever dream in The Forgiving of Monsters. Sonja defeats Death in combat to recover in the real world. This trope is in motion until the first page of the next issue, when Death communicates telepathically that she's not angry. Death knows Sonja's nature and appreciates her willfulness in the first place, and Sonja's rebellion barely inconveniences her.
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In To Hell and Back (Arrowverse), Barry Allen explicitly points this out when explaining to Eobard why he's refusing to go back in time and prevent his mother's murder. According to Barry, all he'd get by doing that is more time with Nora; she'll still die eventually, either due to old age or disease. And while he would love to have more time with her, he isn't willing to do so at the risk of everything he has right now.
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In God of War: Ghost of Sparta the Big Bad is the Death God himself, Thanatos. But this trope is ultimately averted. Death somehow gets killed, even though he is Death incarnate. Its implied Kratos has absorbed his power and become the new death, but since the game is an Interquel it's unknown if he lost this status in the beginning of God of War II.
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Sourcery has, in its prologue, Death come to claim an old wizard named Ipslore the Red. Ipslore attempts to avoid his fate by having his spirit possess a wizard's staff and giving it to his Reality Warper son. Death doesn't seem to get mad, but agrees to let Ipslore continue "living" if they agree on a catch that lets Death claim Ipslore's soul eventually: Ipslore concedes that he will go quietly when his son willingly gives up the staff (something a wizard would never do).
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League of Legends has Kindred, the Eternal Hunters, who are a dual representation of death who appear before those whose time is up. While one half, Lamb, represents a gentle, if absolute version of death to those who accept their fate, Wolf represents death to those who attempt to avoid and cheat it, furiously chasing them until they eventually, inevitably lose.
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The Sandman (1989):
Morpheus, the Anthropomorphic Personification of dreams, uses this trope to his advantage when surrounded by the hosts of Hell intent on tearing him apart. When Lucifer mocks him by asking what power dreams have in Hell, Morpheus responds by asking them what power Hell would have if those within could not dream of Heaven. The host lets him pass without incident.
The very first issue lampshades this. Dream's capture and imprisonment by the sorcerer Roderick Burgess causes all kinds of things (from the merely weird to the truly tragic) to happen all over the world. But when Dream finally escapes, Burgess's son admits that the original plan was to capture his sister, Death. Dream's response is basically, "The entire freaking world should count itself lucky you blew it and got me instead."
It's implied from time to time that pissing Death off is the biggest (and last) mistake a person could ever make. Whenever something irritates her enough to just make her snippy, whoever's doing it stops dead. Even the Kindly Ones fear her.
One inversion exists in Hob Gadling's story, where he gains immortality by basically shit-talking Death. Death finds this amusing rather than enraging. Notably, this isn't even a case of Who Wants to Live Forever?/Blessed with Suck where living forever turns out to be a punishment for his arrogance — Death is still completely willing to take him when he decides he's lived long enough, no strings attached. This is possibly because he shit-talked the idea of death and not Death the individual — if he'd been rude to her, she probably wouldn't have been anywhere near as nice.
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One of John Constantine's fears in the Hellblazer arc of 'Dangerous Habits'. John is dying from lung cancer, and while he's searching for a way to cure himself, he tricks and defeats the literal Devil, Lord of Darkness and King of Hell, into drinking holy water, humiliating him and killing him. The problem is, Satan himself can't die forever, he just returned to hell, and John is still dying, and after living a life of practicing magic and the occult, plus other number of nasty stuff he's done in life, it's only a matter of time until Constantine snuffs it and ends up in the hands of the First of the Fallen, who will do everything and anything short of using his pitchfork into making his eternal unlife a literal endless hell. Of course, Constantine being Constantine, he actually manages to win a second time against not only the Devil himself, but actually the entire Unholy Trinity that rules hell. He sees to it that multiple demons have a claim on his soul, thus, if he dies, it will start a feud. For this reason he is allowed to live, at least until the demons can figure out how to share. Constantine manages, for the time being, to make a subversion of this trope!
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The Cat Lady toys with this idea. The Queen of Maggots attempts to force Susan back to life after she just committed suicide so that the latter can kill off five "Parasites" still amongst the living. When Susan refuses, the Queen points out that, as the gatekeeper between life and the afterlife, she can keep Susan in a perpetual twilight existence, denying her the eternal rest she craves until she does as she's told.
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Soul Music, Death stops working. However, his granddaughter Susan is available as a necessary (but eventually unwilling) replacement.
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Doctor Strange:
In an early story arc, Strange was told he had to meet Death in combat, but he quickly realized that no one can overcome or escape Death. So he surrendered to it, accepting its inevitability — and became immortal.
One of the horrors of Shuma-Gorath and Many-Angled Ones like him is that they invoke this trope in the dimensions they conquer, feeding on the chaos as life grows out of control.
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In Jesus Christ Superstar's song "Poor Jerusalem" is the line "To conquer death you only have to die..."
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Shredder Orpheus has Hades mock Orpheus's attempt to save Eurydice by reminding him that both of them ending up in the Underworld is inevitable. Orpheus counters that since he will get them anyway, he may as well give them a chance to go.
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Charmed (1998): The Angel of Death shows up a few times, and his first appearance revolves around Prue accepting that Death isn't an evil that can be defeated; it's just part of the Grand Design. The Angel and the Charmed Ones clash a few times throughout the series, and the Angel overcomes them every time. In the final season, there's one time where they manage to save someone by going over Death's head and bargaining with an Angel of Destiny, but the end of the season shows that that had been part of the Grand Design all along.
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In the IDW Ghostbusters comic, one of Egon's old college classmates gets hold of the magical bag from the "Russian Soldier" entry under Folklore, and traps Death with it in order to save his life after being hit by a car. In the end, he has to accept his fate and release Death to save Egon (and the rest of the world) from a ghostly Armageddon.
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Darkest Dungeon II features Death herself as a roaming Lone Wolf Boss seeking to hunt down the Flagellant. But the Pale Rider is simply a physical manifestation of her greater being; fighting her is merely Fighting a Shadow, and she will always return to try again.
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In the Hades chapter of Saint Seiya, this question is left unaddressed. In the follow up Heaven chapter, the gods, angry at the dead Gold Saints for killing Hades cursed them to be trapped in a statue for all eternity. Hades being a repeat Omnicidal Maniac didn't affect their judgement.
In Saint Seiya: The Lost Canvas this is actually explicitly referenced. At one point one of the Gold Saints (while living) is teleported into Hades (the location) and notices that all of his dead friends are trapped in the ice of the ninth circle, cursed to this punishment for having opposed Hades. It backfires since their souls help the Gold Saint beat the crap out of his opponent by powering him up. This ultimately gives him enough determination to decide to end things once and for all with Hades, when the next war comes around.
Even with Hades having an ironclad hold on the afterlife, which basically amounts to eternal Hell, a select very few enlightened humans are canonically capable of reincarnation, including Pegasus Seiya (reincarnation of the mythological Pegasus Saint). Hades himself states this with no small measure of surprise, expressing outright rage at being wounded again by the same Saint. So the implication is that without Hades, humans would not go to eternal hell but would have their sins purged through death (as is Athena's wish), and reincarnate freely.
Also, the Jerkass Gods anyway regards humanity as a blemish upon the cosmos, and so would rather condone Hades' Omnicidal Maniac tendencies and gang against Athena.
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The following is a list of statements referring to the current page from other pages.

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 Like a Badass out of Hell
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