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Case #1: The reaper occupies a high rank among The Undead. As such, he is (1) denying the very notion of "death" as we know it, (2) leading an angry mob and (3) offering you a bargain against nature.
Case #2: The reaper is at best the saint patron of Career Killers, at worst an Omnicidal Maniac. He does nothing to cheer you up but makes all existence look empty and condemned. Despair awaits you.
Case #3: The reaper has little if any control over the time and circumstances of your death. More importantly, he behaves like a dignified counselor, genuinely trying to help you to accept reality.
In a world of anthropomorphic personifications, those three may actually fight each other.
Death is under major political slander by Jesus.
Jesus is the first, or at least one of the first individuals to come back from the dead. He and several other resurrectees have banded up to take Death down a peg, as they all think Living Forever Is Awesome. The first example is making Hades a God of Evil in popular culture. Despite this, Death has fought for his reputation, leading to Don't Fear the Reaper examples.
Thanos of Titan is in love with Death because he first saw her as the Perky Goth form.
Which makes his fixation completely understandable.
Death has an entire heirarchy.
Because The Grim Reaper felt it would be easier. These include Decay/Renewal(since without it, death has no purpose), Desertion(death on a grand scale) and Age. Death is led, in turn, by Entropy.