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 (s/he's a hero armed with a Save Point, s/he'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.
- 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.
- 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.
- 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.)
- 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.
- 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.
- This is the origin of Mr. Immortal's power.
- The 2009 Marvel MAX Destroyer series by Robert Kirkman and Cory Walker featured the elderly hero refusing to go with the Grim Reaper squad into the afterlife. One of them makes the mistake of threatening to take his family if he doesn't come willingly.
- 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.
- Marvel's Elders of the Universe were essentially immortal already, but after they offended Death, she refused to accept them, forcing them to live on, no matter how horribly maimed.
- 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.
- 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.
- In Diaries of a Madman, Navarone turns out to be Discord's Arch-Enemy. Discord being the Anthropomorphic Personification of chaos/discord.
- 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?
- 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!
- 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.
- 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".
- 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...
Death: Rather cramped in here, isn't it?
- Turns out there wasn't much room for, say, airholes...
- 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.
- 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.
- 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.
- 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.
- In the Wuntvor the Apprentice books by Craig Shaw Gardner, Death believes that Wuntvor is the Eternal Apprentice, a sort of comic relief version of the Eternal Champion, undying yet forever incompetent, and views his very existence as a personal insult.
- In Legend by David Gemmell, Retired Badass Druss the Legend has visions of Death taunting him; rather than convince him to lie down and die, they just seem to goad him to even mightier feats.
- 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.
- Used for a Downer Ending in Revival by Stephen King: when the protagonist gets a glimpse of what lies beyond the world we know, his Big "NO!" offends Mother, an Eldritch Abomination who appears to be a Cosmic Entity responsible for the miserable state of human souls in the afterlife. Though he escapes immediate retribution, he's not looking forward to what she'll have in store for him.
- The Series 8 finale of Red Dwarf 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:
Rimmer: You can't just whack Death on the head!
Lister: If he comes near me, I'm gonna rip his nipples off.
- The Lexx crew are personal foes of an Affably Evil Manipulative Bastard incarnation of Death.
- This is used at least thrice 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".
- 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.
- In a Halloween Episode of Married... with Children, Death comes to collect Al, and is downright sadistic. Seeing as it can take the form of whatever it wants, it purposely takes one that makes Al uneasy - Peg. "She" isn't unreasonable, however, and says that if his family - who is at Marcy's house - say they need him before midnight, she'll spare him. Of course, she spends the whole time goading and taunting him, at one point claiming he won't like where she's taking him, and then slyly adding "maybe!" Al eventually wins the bet, however, and she honors her end of the bargain, but takes one last jab at him before she leaves, saying she'll be back the day after he wins the lottery. (Again adding "maybe!" to the end.)
- 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.
- Each generation of Belmonts in Castlevania has fought Death (and he just won't stay dead!) Amusingly, Alucard in Castlevania: Symphony of the Night, having been evil and helped his dad Dracula, is on a first name basis with Death when they meet at the start of the game. Doesn't keep Death from punking your equipment, though.
- 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.
- In the first Shadow Hearts game, 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.
- 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.
- 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.
- Happens in Touhou 7: 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 9: 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 Crowning 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.
- 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!!!
- 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.
- 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 triggering the apocalypse, killing all but four people on the planet.
- 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.
- 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.
- 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.
- Haldos, the first Lich and Unreliable Narrator from Nexus War learned his powers in a bid to overthrow Hashaa, the pantheon's death god. Hashaa responded with a Bolt of Divine Retribution that wiped out Haldos' power base in one blow, though he survived in a lesser (but still dangerous) state.
- The Fire God Agni from Kubera fights the god of death just to save Brillith.
- 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.
- 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.
- 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.