Bleach: This trope is in force for the most part. The shinigami are just like humans: they can be friendly, moody, supportive, scary, hostile depending on situation or individual personality type. However, shinigami aren't enemies of humanity even if their focus on the big picture can make them seem aloof at times. Their role is to guide the dead to Soul Society, cleanse hollows of post-death sin so they too can be guided to Soul Society and also to maintain the balance of souls across different worlds. In other words, shinigami are portrayed the same way humans are portrayed: as individuals with their own personalities, worries, fears, foibles, strengths and weaknesses.
This has a lot to do with the fact that in the Bleach-verse, any deceased human with enough spiritual energy can become a shinigami. The fact that the main character becomes one while still alive is a bit of a plot point before the Big Bad shows his face.
The idea is alluded to in Cowboy Bebop, where the Magical Native American says "Do not fear death. Death is always by our side. When we show fear it jumps at us faster than light, but if we do not show fear, it casts its eye upon us gently, and guides us into infinity."
In Kamichu!, Death is a rather friendly, if somewhat eccentric goddess, who even once had an affair with Poverty.
An episode of Yu-Gi-Oh! GX deals with the spirit of the pharaoh Abidos, challenging Judai. After losing, he passes on, satisfied that he finally found an opponent who would duel him seriously. Judai refuses his offer to go with him to the afterlife, but promises to meet him again after 100 years. The episode ends with the crew discussing death and the afterlife. Needless to say, this didn't go well with the translators.
In the end of Puella Magi Madoka Magica, Madoka herself is seen appearing before magical girls whose soul gems are about to be corrupted and taking the gems with her, enabling them to die peacefully and go to the afterlife without becoming witches.
Death in Gregory Horror Show is the only character shown to be completely friendly to the trapped guests, speaking kindly and offering to help where he can.
Played with in Death Note. Shinigami have Blue and Orange Morality and most don't give humans and their lives very much thought. At the same time, they're not all bad — Ryuk really seems to enjoy hanging out with Light and often spends time doing goofy stuff like playing video games in his room. Two Shinigami fell in love with a human and used their powers to extend her life. In spite of their pleasant nature, Shinigami will never be "good" as it's understood by humans. Gelus and later Rem saved Misa's life but were both killed because Shinigami can never use their powers to prolong the lifespan of mortals, and after knowing and hanging out with Light for so many years, Ryuk was all too happy to kill him as soon as he stopped being entertaining.
In Spirited Away, Chihiro takes a train to get to Zeniba's home which is intended for use by the dead moving onto the next life; it has phantom passengers.
The classic modern example is the Perky Goth version of Death from Neil Gaiman's The Sandman and The DCU, although she can appear more horrifying to those whose life was asking for a shocking exit. She used to be the fearsome and cold kind of Grim Reaper, but she matured into the Perky Goth after spending some time among the living.
Martian Manhunter's species worshipped H'ronmeer, the god of death and fire (though some regard him as a god of life and light), who called all Green Martians his children. He was blamed for the plague that wiped out the Martian race, though it was actually Ma'alefa'ak's fault. On one occasion he seemed to be coming after J'onn, but he actually just needed his help to lead the Martians' souls to the afterlife.
The French Comic Le Collège Invisible has an incarnation of Death quite similar to Gaiman's Perky Goth, and possibly inspired by her.
Brazilian comic Penadinho (known in English as Bug-a-booo) has Dona Morte/Lady McDeath, a clumsy Grim Reaper who is always forced to run after her "next clients". Her creator states (link's in Portuguese) that the character is an attempt of making death less scary than most people treat it, and tries to portray her as just someone doing her job, never an assassin.
The Marvel Universe's Death is like this. She seems like a nice girl, if a little dead inside. Wade Wilson, prior to becoming Deadpool, even fell in love with her, and one of the reasons he can't die is because one of her jealous suitors made him immortal so he'd stay away from her, which is another reason why Deadpool is so freaking Axe Crazy.
Amazingly, she's been shown to reciprocate his feelings—but they can only meet during the few seconds after he dies and before his mutant power/immortal curse can call him back to life. Death as a star-crossed lover?
Death has also appeared as a low-key but friendly construction worker, to Jean Grey.
In another X-Men related example, New Mutant Dani Moonstar once tried to fight off an incarnation of Death from taking one of her (non-mutant) friends. She eventually allowed Death to do her job, after she explained why her 'gift' was not to be feared by those who were suffering.
She can stop being nice if she wants to. When she appeared to Dracula - who she clearly didn't like - she took a male form that was far more intimidating.
This is all very much Depending on the Writer. In any story involving Thanos (which, arguably, constitutes most of the stories she appears prominently in), she is presented as a cruel, greedy, and insidiously manipulative being who enjoys causing suffering almost as much as causing death itself; and is generally depicted as the very antithesis of DC's compassionate version of Death. At best, she is Lawful Neutral, often crossing over into genuine evil (she actively seduced Thanos into becoming the living murder machine he is, while still always keeping him lonely and miserable). The reason her relationship with Deadpool is so funny is because it's so unusual for her to react with sincere affection (let alone love) to anyone.
Although Cernunnos, the Elder God of Death from Joseph Michael Linsner's Dawn series can definitely take terrifying form if he so chooses (if, for example, he needs to curb-stomp a group of angels and demons who've decided to trespass on Earth with their bickering), the one time we see him welcoming a soul to the afterlife, he takes a much more attractive form and greets her...very warmly.
In Post-CrisisWonder Woman as conceived by George Perez, Hades is depicted as a relatively benign god who is actually rather kind and generous as far as his job description allows and nobody has an especially significant problem with him. Very much dependent on the writer though.
Bernie in Death Vigil doesn't actually claim souls at all - instead, she focuses on combating primordial forces of evil that want to eat reality.
Mortis from the Pony POV Series, the Anthropomorphic Personification of Death and Grim Reaper, is a pretty nice guy, all things considered. He isn't depicted as malevolent and wasn't complaining that there wasn't much need of him in the G3 reality, barring the occasional accidental death, due to everyone being immortal. He also seems to have no problems letting a soul remain to until its Unfinished Business is completed as the G2 mane cast were permitted to remain on earth until they could pass on together.
Starlight, of the G2 Mane Cast, gets a job as one of Mortis' angels of death after her own, greeting freshly dead ponies to the afterlife. Overall, she's still basically the same good hearted pony she was beforehand.
The Reaper in A Growing Affection appears as a beautiful young girl, is quite kind to almost everyone, and only smiles in amusement at Naruto's borderline blasphemy. And the second she gets a chance she pulls out a scythe bigger than she is and cuts Orochimaru's soul in half.
Fritz Lang's Der Müde Tod* literally "The Weary Death," commonly titled in English as "Destiny" or "Between Two Worlds" centers on a young couple's encounter with an unhappy Grim Reaper who is sympathetic to the woman's pleas to return her husband but unable to actually control who dies and when they die. He refuses to accept her attempt at suicide, tries to comfort her, and gives her the chance to save her husband by changing destiny herself. After all her attempts fail, she sacrifices herself to save an infant whose life she had briefly considered trading for her husband's, and the couple are reunited by Death.
In Adam Sandler's movie Click, Christopher Walken plays "Morty," a peculiar Bed, Bath & Beyond store clerk who is secretly the Angel of Death. He is nice enough to the protagonist, and after dying from misusing the remote, Morty gives him a second chance at life, to be able to truly appreciate his family.
In the movie adaption of The Halloween Tree, Mr. Moundshroud (heavily implied to be the manifestation of Death), while not the most friendly individual, he also bears no real malice to the children; it's just business to him.
In The Seventh Seal Death seems like a reasonably amiable fellow, even postponing someone's demise to play a game of chess. Death isn't particularly malicious or even spiteful towards Block but rather affable, in one scene he even acts as a sort of confidant for Block's confession and angry rant against God. That being said, Death will do whatever he can to win the game.
Death from Monkey Bone, despite having a nasty temper and dark sense of humor, is quite friendly and a rather Benevolent Boss to her reapers. Being played by Whoopi Goldberg definitely helps to play up her perky and cheerful personality.
While Death from the Discworld series is still probably not the kind of person (or Anthropomorphic Personification) you'd like to meet in a dark alleyway, what with him still being the classic cowled skeleton and all, he's arguably the closest thing the Discworld has to a responsible, benevolent deity. (The actual gods tend to be self-interested jerks running on Greek Mythology rules.) He stated that he has to care in order to do his job, although it's an extremely lonely one. After all, no matter how kind he is, people are still rarely pleased to see him (except under certain very unfortunate circumstances). Interestingly, despite him being a skeleton, there have been a fair few fans (some imminently due to be "collected") who've written to Terry Pratchett saying that they hope that he wasn't too far off the mark. Pratchett also says that these letters usually cause him to spend some time staring at the wall. His family motto is "Non Timetis Messor" — Latin for "Don't fear the Reaper" — not to mention he's very fond of cats (it's suggested that cruelty to cats is one of the very few things that can make Death genuinely angry, and he also has adopted rather a large number of his own, which by all indications he takes quite good care of).
Note also that as an actual central protagonist in several books, a great deal Death's characterisation is dedicated to his problems. Fiction rarely depicts the reaper after the soul of their client has moved on, but the Discworld Series does, and it illustrates what it would be like to actually have to have such a role. It's not at all a pleasant duty and he isn't allowed to interfere, so the same empathy that makes him sympathetic to others also brings him great pain and sadness.
There's a book in the series, Reaper Man, devoted to Death discovering how vital kindness in his job is.
A major part of the plot in the later half of the book is the risk of this trope being averted. Death is only to be feared if you've made him your enemy. The new emerging Death of Humans is exactly the sort of Death that should be feared.
One of his most telling moments in the whole series is when he has to kill a chicken in Reaper Man... and is utterly horrified. When asked why, he explains (quite reasonably) that he never murders or "takes" life. He simply takes over where life leaves off.
When Death takes over the duties of the Discworld's Expy of Santa Claus in Hogfather, he thoroughly enjoys the role, as it allows him to actually interact and even improve lives rather than just sweep up after the lights go out. The crowning moment comes when he refills The Little Match Girl's hourglass rather than collect her soul.
Death has also been replaced temporarily by his apprentice Mort and Mort's daughter (Death's "granddaughter") Susan Sto Helit. One is a knobby-kneed adolescent male who gradually starts taking on Death's traits while the other is a young woman. Death and Susan are also two of the only things standing between humanity and the auditors. And boy have they done a good job there...
The Book Thief is narrated by Death, who is amusing, non-linear and very compassionate towards humans (he specifically states he's haunted by them, especially "the ones who are left behind"), particularly the other main characters. Given that it's a book about World War II, the "amusing" part takes a sharp turn. The death camp scenes, unsurprisingly, are particularly bad.
Thanatos (aka Zane) from Incarnations of Immortality will take time to talk to his clients and give whatever comfort he can (if they need it). He's also managed to prevent a few deaths he thought unfair or unnecessary. At least one other character comments that he has an unusually caring approach to his Office.
While Harry Potter never encounters Death, according to Harry Potter and the Deathly Hallows, Harry's ancestor — the one who received Death's invisibility cloak — befriended him, and when it was time for him to die, he sought Death out and they walked away together. Later on in The Deathly Hallows, Harry dies briefly, and his guide into the afterlife, should he choose not to go back, is Dumbledore. Really, death gets a pretty good rap in this series.
It all has to do with the Aesop about how to deal with death, stemming from when Rowling's mother died. If one doesn't accept their own mortality (i.e. the first Peverell brother, Voldemort), or gain acceptance of their loved ones' passing (the second brother, Snape), then Death will be a grueling bastard. But if one accepts Death's visit as an inevitability (the third brother, Harry), then he will greet you like an old friend.
Indeed, the true "Master of Death" as described in the legend of the Deathly Hallows isn't someone who has found a way to avoid death. It's someone whose experiences with the three Hallows has taught them that death is inevitable, it is not a thing to be feared, and that there are far worse things.
TG From The Dead Detective series is a totally happin' dude.
The Spanish novel La Dama del Alba (The Lady of the Dawn) is about Death visiting a family (that has been mourning the death of one of its members for years) in the form of a woman. She notes how she envies mortals for their capacity to love.
The "Death as a gentleman" concept is Older Than They Think: the Emily Dickinson poem, Because I could not stop for Death describes Death as a kind, polite suitor, much like his Discworldian counterpart.
American Gods has Jacquel and Ibis, who are the Egyptian gods Anubis and Thoth, currently living as undertakers in Illinois. Both are very humane people who treat the dead with respect and bring some comfort to their surviving family members. Even if they do, ahem, sample the product.
In His Dark Materials, each person has their own personal Death who follows them around and eventually leads them to the underworld when they die. These Deaths are quite amiable, to the point that most hide from their owners because the people don't want to see them. In addition, the witches believe in a death goddess named Yambe-Akka who arrives, smiling and kindly, when it's your time to go.
In the second novel of the Last Herald-Mage trilogy, Vanyel meets the "Shadow-Lover" — one of the Valdemaran interpretations of Death. To the gay Vanyel, he appears as a beautiful young man, and when he allows Vanyel a short chat with a recently-departed fellow Herald, said friend refers to "Lady Death."
In Tais Teng's anthology Glass Spears, the opposite trope is lampshaded. In reality, Death is a kind, elegant aristocrat with a cloak in "a flowing caleidoscope of constantly shifting colors and patterns that made all people long for the calm, the final change."
Although there is no reaper in the Old Kingdom series, the River of Death — especially the Ninth Gate — is a fairly benign, or neutral place. And Sabriel's father insists that she understand: "Everyone and everything has a time to die."
In the Tortall Universe, the kindest and most forgiving of the gods is the Black God of Death. Notable in that he's one of a handful of deities that actually gives a shit about humans. He's gentle and never makes any effort to intimidate or scare mortals who may see him. The rest of the gods merely use them for power in their own quarrels, and are difficult even for their chosen servants to interact with.
The Lady on the Grey of The Graveyard Book. She even dances with Bod during the Danse Macabre, promises to let him ride her big horse in the future ("Everyone does") and tells the dead to take good care of him.
Richard the reaper from Silicon Wolfpack has a major sense of humor, and is reasonably sympathetic toward those he meets in his line of work.
While Námo Mandos is not actually the god of death in J. R. R. Tolkien's Arda, he is the benevolent Vala (archangel) who collects and judges the dead, and one of the Council of Angels of Valinor. The Silmarillion actually drops the AnviliciousAesop that death is a fate that's intended by God for humans, it's all natural and you should not fear it.
The Many-Faced God of Braavos in A Song of Ice and Fire is a death god spoken of in very positive terms. One of his worshipers makes a comment (slightly paraphrased) that every person has a dark angel beside them, and when the suffering of life becomes too great, that angel will give them the "gift" of death.
The Dresden Files: In Ghost Story, when Father Forthill's life is in jeopardy, Dresden has a conversation with an angel of death waiting nearby. Dresden assumes he'll need to battle the angel to prevent his friend's death, but the angel assures him that (a) she is there only to guard the soul, should it be released from the body, on its way to a final reward, and (b) it was Forthill's choice to enter the conflict, the angel had no part in it (indeed, they don't have free will as humans do). And (c) she would utterly stomp Harry if he raised a finger against her.
In Skin Game, Harry gets to meet Hades himself, who stops time so they can have a chat, and so that the freaking God of the Underworld could express a sense of sympathy and respect for Harry, including pointing out all they had in common (scary reputation, having responsibility for a fortress/prison full of nasty things, friendly, but very dangerous dogs, an iron-clad sense of duty, etc) and wanting to shake his hand.
In Cerberon, Edu, the goddess of death, is described as loving and merciful in her duty to provide rest and comfort after death. She's in charge of keeping the dead from bothering the living, but doesn't seem very proactive in this regard, considering all the zombies, ghouls, vampires and ghosts hanging around, although she does promptly respond to her priests' calls to take them away.
Considering that the main characters are almost all Grim Reapers and are by and large extremely likable people, Croak has this in spades.
Garovel of The Zombie Knight is this. He resurrects the protagonist in order to save other people from dying. However, many of the other reapers do not look so favorably upon the living and prefer to cause destruction and death.
The Screwtape Letters: The apprentice demon Wormwood is delighted to hear that England is under attack, since that will cause plenty of woe and death. However, his uncle Screwtape chides him for thinking that way because Wormwood's target is now a Christian, meaning if he dies he'll go to heaven. According to Screwtape, human fear of death is actually a demonic tactic, to deceive humans and keep them from realizing that they have nothing to fear from death.
Screwtape: They see death as the greatest evil and living as the greatest good because we have taught them to do so. Do not be infected by our own propaganda.
The Twilight Zone TOS episode "Nothing in the Dark". A woman frightened of dying allows a wounded police officer (played by a young Robert Redford) into her apartment. When she realizes that he's Death come to claim her, he tries to convince her that she shouldn't fear death.
Mother, give me your hand... You see. No shock. No engulfment. No tearing asunder. What you feared would come like an explosion is like a whisper. What you thought was the end is the beginning. — Death, assuring the old woman that her journey has just begun.
"Am I really that frightening? Before you knew who I was, you sat with me. Talked with me."
With one or two exceptions, Death is regularly portrayed as a very polite man — often a businessman wearing a nice suit. Which, when you think about it, is probably a good thing since his job is to "welcome" people into death, not to make them run away from it.
One character gets to make a deal to extend his life to finish his life's ambition, to make a really important sale. Death agrees but is annoyed that the character has decided to quit selling anything and says he'll take a life of a little girl instead. Cue the character attempting to sell Death a collection of worthless trinkets (ties, threads and matches) in order to make Death miss his appointment with the girl, thus completing his life's ambition of a big sale that made a difference. Either Death set the whole thing up just to make his client feel better or you can trick him by selling him cheap shoe polish; either way no need to fear him.
The 1980s-era revival featured an episode where Death was cold and emotionally distant, but not evil or malicious. He regards a woman who has become fascinated him with curiosity, but never animosity; eventually, he allows her to become his partner and she embodies the trope more closely by helping to comfort the dying as they are taken.
In the 2003 revival, the episode A Night In Mercy, Death is a kind man who doesn't like his job at all and admires a doctor for having the power to give life. Death decides to give up his job, and the doctor quickly finds out how vital it is when incurable burn patients are unable to die and are thus left in agony. When the doctor dies at the end of the episode, Death admits that he's tempted to let him go back to life, but both of them agree that it's just the way things go.
Touched by an Angel has Andrew, who's a cheerful, friendly, and attractive 30-ish man. His predecessor Adam (not that Adam... probably) was also a pretty nice guy.
Played with in Dead Like Me: the reapers are all former semi-normal people, and are often quite friendly and reassuring, but are also likely to steal from the newly dead and basically behave like people in a customer service job they're not being paid to do.
Tessa, one of the Reapers. Admittedly, some of the other Reapers we see range from creepy to outright scary, but Tessa appears to spirits as a gorgeous, compassionate, and genuinely sweet servant of Death, and Sam and Dean even willingly save her from meeting a grisly fate in season four. Though during her role there, she's a bit more snippy than in her first appearance, mostly dismissing the brothers when they try to help a dead young boy who has yet to pass on. The reason being, for the latter, was that she was supposed to take Dean, until he was brought back to life by Azazel, thanks to his dad making a deal.
Death himself, the boss of the Reapers, also appears. Death is a Cosmic Entity who is as old as the universe and about the same age as God. He runs on Blue and Orange Morality and has seen the death of entire galaxies and will eventually reap God! Hence, he is extremely pissed off that he is bound to one tiny planet circling around a barely newborn sun in a young galaxy that usually wouldn't even be a blip on his radar, due to "a spoilt brat having a tantrum" (a.k.a Lucifer). Dean has a little problem swallowing his pizza after being told this. Just a gentle reminder that, no matter how much of a threat Lucifer may seem, there is Always a Bigger Fish. A much bigger fish. This Death is also given a very human trait, one he shares with Dean: he really likes cheap but tasty food such as pizza, bacon dogs, and fried pickles.
In a later episode Dean wants Death's help to restore Sam's soul and Death gives him a test where Dean has to do Death's duties for a day. Dean fails the test but attempts to fix his mistake as much as he can. Death is impressed that Dean was able to understand how serious and important Death's job actually is and gives Sam his soul back.
When the Winchesters deal with Death he's usually quite snarky and dispassionate because he feels they're wasting his time by asking him for favors. However, when he's actually reaping someone he appears quite polite and complimentary and finds it an honor to guide specific people to the afterlife.
Death is a recurring character in the older BBC series Mulberry, which is appropriate given that the titular character Mulberry is his own son, tasked with cheering up a dour old woman before Death comes to call on business. He spends a good deal of his appearances arguing with Mulberry about how his job isn't a bad thing and how he'd like it if Mulberry would stop asking for extensions on the time he's got.
After years of begging for Death, Al Bundy gets his wish. Good news: Death offers Al a way out. Bad news: Death can assume any appearance, so naturally it chose his wife Peggy. (And is quite a Deadpan Snarker to boot.)
Weirdly enough, there is an NCIS episode that implicitly features the Angel of Death. She appears as a little girl, and mostly just appears to be dropping in to check on her next cases.
The Devil: Now, you're all here for..... Eternity! Ooh, which I hardly need tell you is a heck of a long time, so you'll all get to know each other pretty well by the end. But for now I'm going to have to split you up in groups. Will You Stop Screaming!
Subverted in an episode of Mysterious Ways. Declan starts worrying that his teaching assistant, a not at all scary looking young woman, is the Angel of Death and she has come for him. Throughout the course of the episode, and in dealing with his own potential illness, it is revealed that she is actually the Angel of Comfort (the same one who visited him when his dad died.)
Several Angels of Death appear in Charmed, one in the form of a friendly black janitor, and the other in the form of a wise, insightful (but very, very snarky) British guy.
The Franz Schubert song Der Tod und das MädchenDeath And The Maiden (1817), set to a poem by Matthias Claudius, has Death say to the maiden of the title, "Give me thy hand, thou young and tender form. I am a friend, and come not to punish. Be of good cheer! I am not savage. You will sleep softly in my arms."
Death on Hennepin by Boiled in Lead, takes a more stern tack but ultimately the Reaper in this song is also present to ease the deceased's passing, not harm her or frighten her.
The Demons and Wizards song "The Fiddler on the Green" presents Death as a sympathetic character who takes a young boy too early by accident. He ends up taking someone else (who is implied to have volunteered) so the boy won't have to be lonely in the afterlife.
"When the Saints Go Marching In," a Christian hymn, best known today as a jazz tune by Louis Armstrong. Popular as a funeral march in New Orleans, it treats death as joyous occasion for those who are going to heaven.
The song itself, however, is about the Second Coming, the Resurrection of the Dead, and the New Creation. Death is only mentioned indirectly by referring to "those who have gone before."
Rage's album Speak of the Dead features a Grim Reaper in several songs who is "Heaven-sent" as a mercy to free one from pain, and wishes not to be feared.
Mythology and Religion
Maman Brigitte, the Hatian goddess of love and death. To quote God Checker:
"She is so chatty and full of jokes that it's fun when she escorts you to the Underworld."
Baron Samedi, Papa Guede and the whole rest of the Guede family, which tends to be a bunch of people who really enjoy... for a lack of a better word, living. Papa Guede himself sits down and listens to your entire life story.
The character of La Catrina is an important part of Mexical folklore. She is nice, loves to sing, dance and have fun with the mortals, especially on certain days like Dia De Los Muertos ("Day of the Dead"). And if you are Mexican she will appear on the day of your death.
Death is also revered in Mexico in the form of Santa Muerte ("Saint Death"), who is worshiped as an unrecognized saint. While still taking the form of a grinning skull, she is revered as a patron of the downtrodden and those forsaken by society at large. She is also worshiped by criminals as the one saint who will never forsake them.
Some scholars of The Bible take "Angel of Death" to be an allegory for Jesus. A large number of angels also bear the title. The Islamic figure Azrael is probably the most famous today, but Michael and Gabriel also qualify. Of course, Satan is also credited as an "angel" of death, so...
Jesus even explicitly states that angels come to get people when they die (Parable of the Rich Man and Lazarus). Of course, they're not the ones you should be afraid of, but rather God, who judges you. The angels will escort the faithful to Heaven, but they'll also dutifully cast the wicked into Hell.
Though it's not agreed whether this is doctrine or folklore, some Mormons believe that it is your already-deceased family members who come and get you when you die.
Older Than Dirt: The Ancient Egyptian attitude towards death was not one of horror. Though they believed that those who offended the gods would suffer in the afterlife, their religion featured lovely, kind deities who welcomed the dead to The Underworld with beer and food.
In Norse Mythology the valkyries, female spirits, are reapers of the souls of dead warriors deemed worthy of being taken to Valhalla. Then again, it's very subjective if Valhalla is such a nice place to be. People who died of sickness and death went taken to Hel and Helheim, a shady but peaceful place. Hel is monstrous in apperance but a neutral deity that is understood to be kind, from what is understood from the poems.
When Death comes for Lisa in Funky Winkerbean, he is a perfectly-mannered well-dressed gentleman (albeit with a theatre mask hiding his face) who makes an undramatic entrance, allows Lisa to realize for herself that "It's time" and extends his hand for her to take, and lets her pause for a moment as he leads her away so she can say goodbye though it goes unheard.
The Undertaker, at least since his 2004 return to his "undead" gimmick. He's still depicted as intensely scary and having supernatural powers, but he usually battles against villains - most famously at the 2007 Royal Rumble, when he arrived as the 30th entrant to save Shawn Michaels, Edge, Randy Orton, and Montel Vontavious Porter from The Great Khali.
The Forgotten Realms setting really likes this trope. Kelemvor is the poster boy for this trope and canonically Lawful Neutral. He and his worshipers work to comfort the living and ensure that the dead rest in peace. The setting also includes the halfling death god Urogalan, also LN, and the Mulhorandi god Osiris who is Lawful Good. Even Kelemvor's unnerving-to-mortals subordinate Jergal counts, as he is merely the archivist of death.
In the Greyhawk setting, Wee Jas is the Lawful Neutral goddess of Death and Law. Her clerics teach that death is part of the natural order, and that she shepherds the souls of the deceased to their final destinations.
At least one god of death (a converted version of Hades) is explicitly stated to only be evil because the alignment was required for levels in the Assassin class, but would otherwise be True Neutral. Which makes sense.
The Sims series has a light tune of the Grim Reaper, he listens to pleads for life, and he gives a chance for the Sims to win back their loved ones, and even if they failed at his little game, he might bring them back as zombies anyway. He also gives discounts on children's resurrections. He enjoys watching TVs and if he arrived at a party, he might party with the residents, even though he always spoils the mood with his arrival. Oh that silly Reaper.
If a sim dies of old age while in Platinum Aspiration in The Sims 2, the Reaper shows up in a flower lei, accompanied by hula girls, to send your sim on an eternal vacation to Tropical Paradise Heaven.
One of the plot hooks in Strangetown is the product of an affair between the local Black Widow and the friendly guy who kept coming for her husbands.
Though he does have his temper. In Sims 3 University Life, if you rant against him, he will strike down your sim. He does resurrect them and tells them not to do that again as he's got a job to do.
Mara, one of the gods from the Incursion, puts a big emphasis on fulfillment and resolution; she is surprisingly free with resurrections for her worshipers. Unusually for this trope, she is also the goddess of The Undead and doesn't view them as abominations.
Maximo has Grim, The Grim Reaper, who is a all around pleasant guy and a wise-ass. The second game shows that it's not just a job for him, he feels paternal to the souls he guards and hates to see them trapped or used for evil. In fact, in the second game he even directly helps Maximo this time by functioning as the game's Super Mode, temporarily replacing Maximo.
The Master of Death of the protagonist's homeworld, Vigilance, was picked for the position by the world's chief god specifically because of his kindness and compassion, knowing that he would be far more appropriate than anyone callous or indifferent. Unfortunately, Median believed he was responsible for causing death and killed him, leaving the souls of the dead unguarded and causing souls to be slowly stolen from the world.
Gig, a Master of Death from another world, is an aversion: He's cruel, genocidal, rude, arrogant and essentially void of redeeming characteristics. He was sent to kill every living thing in Haephnes and did a pretty good job of it until Median's daughter managed a double knockout and sealed his soul into a black sword. Later revelations make it clear that Gig and Vigilance are the same person, but the god Drazil corrupted his soul because, once again, there was no one to guard it. It was then sent back. As Gig slowly awakens to his former life, he mellows out and reaches a middle ground between the perfect and compassionate Vigilance and the omnicidal Gig.
Touhou, of course, sticks its thumb in this pie, as well. Not-so-grim reaper Komachi is often portrayed as a Hard-Drinking Party Girl whenever she isn't napping for days on end. She basically just wants to "go at her own pace", which happens to be lethargic, even by a (non-flying) turtle's standards, and is notably bright and cheery any time it involves anything besides the drudgery of actually doing her job. Fanon aside, it seems her sloth actually comes from trying to do her job too well and spending too much time with each soul rather than working efficiently and heartlessly to meet her quota like she's supposed to. She also takes breaks to give advice to the living.
Komachi's boss Eiki, who judges the dead, is often portrayed equally comically by the fandom, as a workaholic who spends much of her time stressing out about Komachi's (lack of) work habits, and her own days off committing laughably minor misdeeds.
Krypta, the Goddess of Death in Majesty, is apparently quite compassionate and egalitarian. One of the character vignettes has a priestess of Krypta teaming up with a Paladin of Dauros to destroy some monsters who had been killing pointlessly.
Death of Death Jr.. is portrayed as a family man who, in the comics, is happily married to a human woman and is a father who, while stern, is generally willing to show his son aspects of his job. As he once says in a comic book offshoot, "Son, there are two things you can always count on: taxes, and your old man."
Nyx, the ultimate foe in Persona 3, is the Anthropomorphic Personification of Death itself, but is portrayed as an unknowable entity beyond good or evil. It doesn't bear any malice towards anyone, it just is. However, its earthlypersona (appropriately named Nyx Avatar) is affable, friendly, compassionate, and —though invincible and relentless— sympathizes with the protagonists and their plight, fighting them only to take them to their absolute limits to see how strongly they cling to life.
In the end, Nyx acknowledges the Main Character's selfless sacrifice and personal fulfillment, allowing itself to be defeated and stopping The End of the World as We Know It that it was about to bring. And then, Nyx Avatar has nothing but kind words and inscrutable wisdom to congratulate the Main Character and his/her friends with. And then The Answer explains that it's not Nyx itself that would bring about The End of the World as We Know It, but an Eldritch Abomination made up of mankind's negativity and willingness to die (helped along by Takaya starting up a cult and whipping as many people as he can into an apocalyptic fervor) coming into contact with it.
Also of note is that before he even became Nyx Avatar, he previously took the form of Ryoji, a transfer student to Gekkoukan High, who is not even aware of his own destiny at first. He behaves quite cheerfully, and the only person that suspects something is amiss is Aegis.
Manny Calavera of Grim Fandango and the page quote is a charming salesman; it just happens that he sells travel packages to carry dead souls safely through the afterlife. His job and that of his fellow Reapers is simply to ensure people get what they deserve. Most of them aren't scary at all. In fact, when an earlier Reaper, Salvador, learned that good people were being denied their "sweet hereafters" and being forced to linger in the Land of the Dead, he quit his job, denying himself his 'benefits', and started a revolution.
Death in the Neverwinter Nights 2 mod saga Dark Waters is portrayed as a long-suffering hard-working bureaucrat who decides he's just not going to process your character because he's busy, thus excusing your deaths in-game. This is Played for Laughs.
The actual Reaper of Hordes of the Underdark is benign, and merely opens many doors for you to take once you reach his realm, provided you have the means of paying him to be resurrected... This is later used against you once it is revealed that his true name was discovered by the Big Bad Mephistopheles. Said archdevil used him until the perfect moment so that the hero would be trapped in Cania (read: Hell) and so that the Reaper would not be able to help them escape.
Similarly to the Dark Waters example, Death in AdventureQuest always tells you he has filled his quota of souls for the day, and sends you back saying you owe him one. For whatever reason, he never calls in the favor. Again, played for laughs.
Death in the first Hatoful Boyfriend is just a card of a reaper with a bird skull for a face, whose appearance on reaching a Bad Ending can be alarming. But in the next game, Holiday Star, he's the conductor on a train carrying souls through the afterlife, and is amiable and a little folksy. The protagonist cheerfully claims familiarity with him and even says that they are friends, which he doesn't dispute.
She says they've been friends since the demo, and implies it's because she's had so many bad ends. This would imply that she remembers all her bad ends.
The Spirit Monk from Jade Empire can be nice and helpful to departed souls if the player chooses. The Spirit Monk's boss, the Water Dragon, spends most of the game incapacitatedin a grisly fashion, but takes the form of a benevolent, kindly woman known as the Shepherd of the Dead. Like a Jesus/Guan Yin combo.
The grim reaper in Napple Tale is a odd, overly-polite little flower fairy creature who is the butt of a lot of jokes over the course of the game for incompetence. Granted, he earned it when he claimed the heroine instead of the cat he was sent for.
Gashapon Shop has the Grim Reaper's angsty nephew, who, on his first day, goes for his target's nephew to to slightly similar names. He later cracks a few jokes and aids the heroes, but he doesn't show up often.
Gunnerkrigg Court has the guides, friendly minor deities who help each dead person or animal into the Ether. They range from fuzzy dogs to old women to an owl-headed guy to, well, Ketrak. We never see him, but Word of Tom states that Ketrak's appearance is a comforting sight for the souls he escorts. Of course, he's the Guide for Insects, so for normal humans he looks Brain Bleach-grade horrifying.
The title character from the webcomic Jack is ass-ugly, he's mean, he WILL hunt you down viciously if you try to run away from him, he's one of the Seven Deadly Sins, and in life, he was an evil dictator who wiped out all of humanity. However, he also genuinely cares about the souls he guides to the afterlife (to the point that he gets mad when reasonably decent people get condemned to Hell), and even denizens of Hell. And sweet mother of potatoes is he nicer than the other sins.note Except Sloth. But Sloth is merely the ground of Hell, so it's disqualified.
Finders Keepers features a Gaiman-inspired Perky Goth Death, the youngest of the nine Powers That Be, the highest authorities beyond The Veil. She does have rather nasty skeleton-and-cowl enforcers. She seems to have a soft spot for Card, though.
Death from Slightly Damned, though initially intimidating, is actually very friendly. However, that Death has been revealed to be the angel Darius, the adoptive father the boy he is hugging. The real Death appears to be much less pleasant.
In The Adventures of Dr. McNinja, Death, while still retaining the black clothing (albeit a suit) and skeletal appearance, is a mostly-polite British waiter who guides you to your table in Purgatory, which is a restaurant.
Dee, from the Spanish webcomic CROWLEY, usually looks like a cheerful little girl and is quite friendly and kind, and a friend of the main character. Unless you piss her off, then she can be downright terrifying.
Death in Problem Sleuth is a nice enough guy, willing to let you drink tea and play games for your life. He's also pretty ineffectual at his job, as most of the characters who end up in the afterlife escape through the door.
Death in Muertitos takes the form of a vaguely humanoid mass of black, inky substance with a single eye. While somewhat creepy, he's a reasonable enough guy, and popular enough to have once had his own children's cartoon.
The scrapyard robot in Freefall is pretty nice for a robot built to take apart other robots (and who carries a scythe). He even allows them to buy themselves as scrap so they don't need to be disassembled (not to mention exist without an owner).
While the other "The Last Trick-or-Treaters" strips by R.K. Milholland of Something Positive fame are frightening, this one starring the Grim Reaper and an unfortunate trick-or-treater is oddly touching.
In The Order of the Stick: Malack argues that while death gods get a bad reputation, they should be viewed as neutral by default. Death claims everyone, not just the righteous. His own patron god, Nergal, is almost certainly evil though: Malack is his high priest and his goal is, after his allies have passed on (from old age or otherwise), to begin mass sacrifices to Nergal on a scale that the gladiator games cannot compare to.
Death in Johnny Wander is an awkward guy who falls in love with a human girl, accidentally skeletonizing her hand with a kiss and then being too shy to approach her for eighty years, which incidentally prevents her from aging. They get together in the end.
Childrinrskary: The Childrin may indeed be scary, but Death, despite the skeleton-in-a-cloak-with-a-scythe look, is a kindly and benevolent figure (and a bit of a Woobie too):
He can be very evil and nasty if you make him angry enough. The Halloween Episode is one good example. At the beginning, he tells Billy and Mandy via Flashback how Jack (as in Jack o'Lantern) tricked him into making him immortal. Grim did so, but retaliated by cutting his head off. ("Gee, Grim, I didn't know you had it in you," comments Mandy.) During the course of the episode, Jack comes gunning for revenge, nearly destroying the whole town, and at the end of the episode, Grim loses his patience and has the guy Dragged Off to Hell, proving he's still got it.
Death in Family Guy is portrayed as an average person, although still keeping the robed skeleton motif. Several episodes have revolved around Peter dealing with Death, and he's often a lot more down-to-earth than most people on the show, though with a tendency to abuse his Touch Of Death to get out of awkward situations. Being voiced by Norm MacDonald definitely helps him be seen a likeable if not somewhat sarcastic guy. Just don't look under his hood.
He's also apparently just as susceptible to death as everyone else. When a Death dies, he's harvested by Super Death, who's the same as him, but taller, and reincarnated. This happened to Death in one episode, but after being reincarnated as a female chinese baby he quickly pops back into existance again
In Mary Shelley's Frankenhole, the Grim Reaper is a bit of a goofball, but every mortal fears him for the obvious reasons. This annoys him when Frankenstein gives him no respect at all as he's immortal and has nothing to fear.