The Problem with Fighting Death

"Kevyn: It's like we stole fire from the gods, or something. Ennesby: In most of those stories the mortals get away with it. Kevyn: Yeah, until they die, and they find out why the gods can afford to be patient."

- Schlock Mercenary

...Is that even when you win, you'll eventually still 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 Guile Hero or sufficiently Badass hero with a good enough weapon and plan.

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/she/it may decide to punt you into Hell instead of Heaven. Even Immortality is no guarantee of safety, since 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 (which is not as contradictory as you'd think) might not offer protection either, as its 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. At least... not unless you get really creative and thorough. If all that matters is that there be A Death, then replacing him with someone friendlier (or at least 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 what's probably not the most pleasant job for the rest of eternity), and flying Like a Badass Out of Hell are all possibilities. These last two have been known to backfire though, in that having Death fear you may make it not want to "reap" you either.

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.

Anime and Manga

 * 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.

Comic Books

 * 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.
 * Incredibly minor Marvel Comics villain Deadly Ernest gained immortality after refusing to die during World War I and fighting off Death itself; he became an immortal with an uncontrollable Touch of Death, something he discovered when he returned home and embraced his wife.
 * In The Sandman Morpheus, the Anthropomorphic Personification of dreams, uses this trope to his advantage. When surrounded by the hosts of Hell intent on tearing him apart, he responds to their challenge asking him what power dreams have in Hell by pointing out that Hell's tortures would be meaningless if the victim was not able to dream of something better. The demons are hesitant to break their own system by killing him and let him just walk out.
 * 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."
 * In The Mighty 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.
 * The french comic Zorn et Dirna has this as its central premise. A king trapped Death in a magic mirror so he'd never die. Neither does anyone else, and while the king got the unaging bonus, no one else did, resulting in people aging into still-living zombies, crying for release. The government deal with this by rounding up the aged (even those who still want to live a bit longer) and sending them to "Les Laminoirs" to have them decapitated (causing the soul to leave the body and possess the nearest person) and storing the souls in the bodies of criminals. Needless to say, it's a short-term solution at best, and many of the hosts become quite dangerous and crazy from housing hundreds or thousands of desperate souls.
 * Became a plot point in an early Doctor Strange story arc. He 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 his type is that they invoke this trope in the dimensions they conquer, feeding on the chaos as life grows out of control.

Folklore

 * In myth, there's the old story of The Russian Soldier, who trapped Death in a magical bag. This resulted in Death Takes a Holiday, so nobody could 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's powers, and fled from him before resuming his duties... Which was all fine and dandy until, of course, the SOLDIER grew old, and Death would not come for him. Growing older and weaker, he became tired and weary of life... Who Wants to Live Forever?, right? He even tried to walk to the gates of Heaven himself, but they wouldn't let him in - he had sinned against the natural order of things by preventing Death from doing his job, after all. He then resigned himself to his fate and walked to the gates of Hell... but the Devil knew of his reputation, and was afraid that he'd be Like a Badass Out of Hell and take over, so he barred the doors and refused to let him in. And so, due to his fight with Death, the Russian Soldier had all paths to the final end denied to him... and some say, he wanders still, hoping for the day he will be forgiven and allowed to rest at last...
 * There's also the tale of 'Jack', after whom Jack-o-lanterns are named, who captured and tricked the Devil into agreeing to leave him alone. All fine until he died, and God wouldn't let him into Heaven for being unrepentant, while Satan wouldn't let him into Hell cos that would count as 'not leaving you alone'. Jack was left to wander through eternal darkness with no home to go to. When he begged Satan to at least lend him a light, Satan carved a demonic face into a gourd or a turnip, and lit it from within with an ember from Hell, presumably so Jack had something to remind him of exactly why you never mess with Satan.
 * The legend of Stingy Jack.

Literature

 * The story of the three brothers from Harry Potter (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; so Death took the elder brother for his own. 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. And so death took the middle brother for his own. The last one asks for a perfect invisibility cloak, and uses to hide from Death for many years. Eventually, he takes it off and gives it to his child; finally Death comes to take him, but they walk off as equals.
 * Discworld examples: Mort picks a fight with Death towards the end of the book; in a separate incident, Granny Weatherwax cheats him at cards to save a child..
 * 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. Mort ofcourse refuses to take the bait.
 * Also, in 'Reaper Man', death literally takes a holiday and the whole book is about the issues that causes.
 * In that case, Death was retired by the Auditors.
 * Malazan Book of the Fallen has example in backstory. 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.

Live Action TV
"Death: You have an inflated sense of your importance. To a thing like me, a thing like you, well...Think how you'd feel if a bacterium sat at your table and started to get snarky. This is one little planet in one tiny solar system in a galaxy that's barely out of its diapers. I'm old, Dean. Very old. So I invite you to contemplate how insignificant I find you."
 * Jim Henson's The Storyteller has a retelling of the Russian Soldier's story.
 * In one episode of Xena: Warrior Princess, 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.
 * Discussed in Supernatural. To stop the Archangel Lucifer, Dean tries to kill Death, 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 six, Dean gambles with Death . 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 season seven, this trope is almost actually achieved when Death doesn't seem to hold a grudge (probably because they're too insignificant), but he warns them not to try that again.

Mythology

 * In Greek myth, as punishment for ratting out Zeus, jerkass tyrant, and Manipulative Bastard Sisyphus was to be punished by being personally taken by the death god Thanatos to an especially unpleasant corner of Tartarus in chains. Of course, Greek myth also spoke of how Sisyphus arrogantly thought himself even cleverer than the Gods. So, the tyrant coyly asked Thanatos how the chains worked, and in demonstrating, Sisyphus trapped the god in his own chains. Of course, this meant that no-one could die at all. Eventually Ares, the god of war, got pissed off because none of his opponents would die when he killed them, which was no fun, so he freed Thanatos and let the god of Death carry on with his mission. This wasn't the first time he cheated death. Another time when Sisyphus was about to die, he instructed his wife not to give him any funeral, shroud, or even money to pay Charon. So, when he did die, he made his way to the palace of Hades where he schmoozed and pleaded with the goddess Persephone that his wife was very, very cruel and disrespectful. Touched by the trickster's words, the goddess permitted him to return to the world of the living to *cough* scold his wife. Of course, when Sisyphus was finally delivered to Tartarus, Hades made a bargain with Sisyphus, in that Sisyphus could walk out of Tartarus scotfree if he could just roll that boulder up that hill, and make it stay there... And we all know how that turned out...
 * Problem averted when Hercules wrestled with Thanatos to keep the god from taking Alcestis, the wife of his friend Admetus.
 * Not quite death, but, Thor once wrestled with Elli, the personification of Old Age, when she was disguised as an old woman by the illusions of the sorcerer-giant Utgardloki. Embarrassingly, Thor had his butt handed to him by Old Age.
 * Not as embarrassing as Thor thought. He lost, but the giants (who knew the old woman was Old Age) were terrified that he had wrestled her to her knees first.

Video Games

 * 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 the backstory of Soul Nomad and The World Eaters, Lord Median The Conqueror killed Master of Death Vigilance to save his son from a wasting disease.
 * 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 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.
 * The Brothers Sun in Jade Empire decided to go off and mess with the Water Dragon, which trapped the spirits of the dead in the world of the living where they quickly went insane and started massacring people.

Western Animation

 * In The Grim Adventures of Billy & Mandy, Jack O'Lantern forces Grim to grant him eternal life, in exchange for returning his scythe. However, Grim decapitates him, and he's forced to use a pumpkin as his head