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In current media the personification of Death is often shown as a fairly pleasant and sympathetic character, as in the Sandman graphic novels and some of the original Twilight Zone episodes. How far back does this characterization go?

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Partly inspired by this question.

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    As the quote goes; "What can the harvest hope for, if not for the care of the reaper man?" Death has always been seen as a semi-sympathetic character, releasing people from their misery.
    – Valorum
    Commented Mar 14, 2015 at 17:48
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    There are many sympathetic characterizations in popular culture and older myth/religions. Going back to Greek mythology, Hades is not always seen as a terrifying figure. For the Egyptians, Anubis is seen as a guide and judge. Various presentations from semi-recent sources might include the TV show Dead Like Me (currently available on streaming services), Pier Anthony's Incarnations series, Bergman's the Seventh Seal, and others. If you wanted to dig into this, perhaps en.wikipedia.org/wiki/Death_(personification) would be as good a starting place as any. Commented Mar 14, 2015 at 18:26
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    Is the image necessary? What does it have to do with the question?
    – user14111
    Commented Mar 14, 2015 at 19:17
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    @user14111 because a picture of a happy go lucky goth death is a million words
    – user16696
    Commented Mar 15, 2015 at 5:28
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    @cde: Don't Fear the Reaper is a better fit. If I had seen this TVTropes entry before, I wouldn't have posted the question. For some reason I was thinking that this was a fairly recent trope. I'll leave the question up for awhile to see if anyone has any surprise answers.
    – Joe L.
    Commented Mar 16, 2015 at 13:48

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One popular and influential story of this type is "Godfather Death" (Der Gevatter Tod), a German folk tale collected by the Brothers Grimm, published in 1812. You can read the German text here, an English text here, an annotated English text here. From the Wikipedia synopsis:

A poor man has twelve children, and works just hard enough to feed each of them every day. When his thirteenth child is born, the man decides to find a godfather for this child. He runs out into the highway, and finds God walking on the highway. God asks to be the godfather, promising the child health and happiness. The man, after finding out that the man is God, declines, saying that God condones poverty. Then the man meets the Devil on the highway. The Devil asks to be the godfather, offering the child gold and the world's joys. The man, after finding out that the man is the Devil, declines, saying that the Devil deceives mankind.

The man, still walking down the highway, meets Death. The man decides to make Death the child's godfather saying that Death takes away the rich and the poor, without discrimination. The next Sunday, Death becomes the child's godfather.

When the boy comes of age, Death appears to him and leads him into the woods, where special herbs grow. There, the boy is promised that Death will make him a famous physician. It is explained that, whenever the boy visits an ill person, Death will appear next to the sick person. If Death stands at the persons head, that person is to be given the special herb found in the forest, and cured. But, if Death appears at the persons feet, any treatment on them would be useless as they would soon die.

The boy soon becomes famous, just as Death has foreseen and receives plenty of gold for his amazing ability to see whether a person would live or die. Soon, the King of all the lands becomes ill and sends for the famous physician.

When the physician goes to see the King, he notices immediately that Death is standing at the foot of the bed. The physician feels pity for the king, and decides to trick Death. The physician then turns the King in his bed so that Death stands over the head. He then gives the King the herb to eat. This heals the King and speeds his recovery.

Soon after, Death approaches the physician, expressing his anger for tricking him and disobeying Death's rules. But because the physician is Death's godchild, he does not punish him. Death then warns the physician that if he was to ever trick Death again, he will take the physician's life. [. . .]

A modern (1953) retelling, "The Third Guest" by B. Traven (author of The Treasure of the Sierra Madre), was the subject of this story-identification question.

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