The Grim Reaper or any god of death is usually a big deal. They're master of one of the most fundamental forces of nature, carry souls off to the afterlife and usually look intimidating. At least, that's how they're usually characterized. But sometimes the scariest thing about the reaper is their job. They always lose Chess with Death, have trouble getting mortals to come with them and nobody respects or cares for the job they do. And if there are other gods, they tend to be The Friend Nobody Likes. Maybe there are multiple incarnations of death, and one of them happens to be the Butt-Monkey of the group.
As death in Real Life is permanent, having something as inevitable and final as death be portrayed as a joke can serve as catharsis for the reader/viewer, or being seen as a joke allows someone to pity them. Maybe the idea of such an important and powerful entity being a joke is hilarious in itself. Of course, they're still The Grim Reaper or a god of death, so don't be surprised when they turn the tables and show a badass side to them.
Sister trope to The Devil Is a Loser and Loser Deity, when Satan and a god/the God is the Butt-Monkey, respectively. While it can overlap with Don't Fear the Reaper, that trope is where Death isn't scary because they're nice, not because they're a loser. Compare Hanging Up on the Grim Reaper, where someone tries to push away Death, but that doesn't mean it's a recurring problem or Death's necessarily a loser. Sub-trope to The Grim Reaper.
- In Black Butler, the Grim Reapers are a bureaucracy to collect the dead. All of them are blind without their glasses and are constantly bogged down in paperwork and assignments. Even their scythes can be blocked by the likes of high-grade cutlery (albeit, supported by Sebastian's demonic strength). To top it all off, their duties are a direct result of their decision to commit suicide in their past lives.
- Death Note: The Shinigami are Gods of Death that collect human lifespans through the Death Notes. While impossible to harm by humans, they're generally lazy and bored who do little if anything in their own decaying Shinigami Realm besides extending their own lives (which means they make a point of killing humans on a regular basis), some even having died by forgetting to extend their own lifespan. They're less "gods" than a breed of supernatural parasites. Sidoh in particular is a joke among the Shinigami who slacked off so much he lost his Death Note. Ryuk is about the only proactive shinigami who started the plot because of how boring the Shinigami Realm is, and the other Shinigami mock him for it.
- Green Lantern: Downplayed with Nekron, Lord of the Unliving. While a legitimately powerful and dangerous Cosmic Entity, he is usually stuck as a bodiless spirit in the limbo-like Land of the Unliving, where he was threatened by the paradox of an immortal like Krona dying, and when Hal Jordan manages to incite the recently dead spirits to rebel against him. While he averts this by being a cosmic threat in Blackest Night, he's only able to do so because of the death of his tether, Black Hand, and is banished to his realm shortly after Black Hand is revived.
- There are numerous stories where Death gets captured by a tricky human. Cf. also Aarne-Thompson 330.
- Bill & Ted's Bogus Journey: After Bill and Ted are killed by their evil knockoffs, Death ends up coming for them. They manage to melvin him and run away, and when Death catches up with the two it leads to a Chess with Death. He manages to lose every single game while insisting on Best Out of Infinity.
- Mort: At the beginning of the story, Death's apprentice Mort is very bad at his job, completely messing up his entrance and unable to go through with the actual scything. Thankfully his first customer is an understanding witch who walks him through it, and It Gets Easier as time goes by. Death even tells Mort that it's a good sign: had Mort shown sadistic pleasure in performing the Duty, his apprenticeship would have been cut short.
- Dead Like Me: Reapers are recruited from the recently dead, have to blend into mortal society, and have no powers other than immortality and a Lie to the Beholder disguise. George ends up with the same low-level office job she held in life, albeit with a much worse apartment since her new identity doesn't have any assets. More senior Reapers are a bit better put-together. Mostly.
- The New Addams Family: The Reaper tries to come for Gomez in "Death Visits the Addams Family". Initially he seems quite cool, being a giant, ominous dark robbed figure, with an inhumanly deep voice and supernatural powers. However, after getting sick of the Addams' antics and them being completely oblivious to who he obviously is, he drops all the theatrics and takes off his cloak, revealing he's in fact a much shorter, bespectacled unassuming man, with a nasally voice who dresses like an accountant. Ironically this version actually manages to get the Addams to take him seriously (after he flat out explains what's going on to them), however, upon them learning you can challenge Death to continue your life, he proceeds to lose every contest to Gomez and ends up falling back into the underworld.
- Red Dwarf: Death himself appears at the end of "Only The Good". As Red Dwarf falls apart, the Reaper tries to collect Rimmer's soul, only for Rimmer (of all people) to casually knee him in the groin, and walk off dismissing it as "Not today thank you, only the good die young." Leaving death to pathetically whine about how that has never happened before.
- The Watch (2021): Unlike his book counterpart, Death is treated as a joke by most of the characters he interacts with, seems more interested in getting accepted in a band than actually reaping, and is shown to have trouble doing his work correctly when he has to.
- The Bible: In the book of 1st Corinthians, Paul the apostle says, "Where, O Death, is your sting? Where, O Grave, is your victory?" when he tells how those who believe in Christ will be resurrected, as "the corruptible" is "clothed with incorruption" and "the mortal" is "clothed with immortality", and when that happens, "death is swallowed up in victory."
- Rayman Origins: Mister Grimm is one of the least threatening-looking versions of The Grim Reaper out there, being a senile old man who's looking for his teeth.
- Downplayed in Have a Nice Death (2022): The tedium and stress of running Death Inc. has weakened the Reaper considerably so he has to fight his rogue employees the old fashioned way, he still has a ton of weapons and spells at his disposal.
- In Purgatony death is at least a Pointy-Haired Boss. While he has power and respect among the caseworkers of Purgatory, he's stressed out by his massive responsibility and having to deal with the resentful protagonist Tony Purgatelli. Also, he has constant technology problems, and his support is quite unhelpful.
- In Animaniacs, the Reaper tries to take Wakko away because he ate too many meatballs. He really does try to be menacing, even appearing with a dramatic light show, which makes sense given that Toons are so hard to kill. He is immediately undercut by appearing in the oversized pile of meatballs. And then Yakko and Dot want to come too, refusing to leave their brother. He tries to trick them through Chess with Death, the stakes being that they get to stay together forever, and on their victory he kills them. But they promptly annoy the Reaper so much he sets all three of them free, much to his chagrin.
- Family Guy: Death is portrayed as a geek who still lives with and is nagged by his mother, and has no luck with with women. He ends up trying to collect Peter too early and breaks his ankle chasing him, making him unable to do his job. He later tries to get Peter's advice on how to get a girl.
- The premise of The Grim Adventures of Billy & Mandy is that Billy and Mandy challenge The Grim Reaper to a game of limbo for the soul of Billy's hamster, with their terms being that if they win, the hamster lives and that Grim becomes their best friend forever — Mandy cheats and wins, thus trapping him with them. They treat Grim like their slave, and despite being legitimately powerful and scary when he wants to be, Underworld rules means he can't break the contract. Ever since then he's become the laughing stock of the Underworld and is one of the series' main butt monkeys. It doesn't help that Mandy is every bit as scary as he used to be, if not more so.
I used to have a chariot of four hundred burnin' horses! My arrival on the scene would be a raging thunderclap of fear! Now it's "Hey, have you seen Grim?" "Yeah! I think he's wedged between a history textbook and a tuna fish sandwich!"
- Death in Mary Shelley's Frankenhole is portrayed as a Large Ham who, while intimidating to mortals, is "goofy" to those who have achieved immortality like Victor Frankenstein and his associates (and to a lesser extent, everyone else in Somewhere in Easter Europe) and have nothing to fear from him. He has long since developed a complex to try and regain Victor's respect, trying to intimidate Victor by threatening to reap his mortal, incredibly old children.
- The Simpsons: In one of the Treehouse of Horror specials, Homer kills Death and is forced to take his place (via Groin Attack). He handles the duties of being the Grim Reaper in the regular fashion Homer Simpson handles everything else.