Mimi - Ch. 47 - Sisyphus.

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Short answer: man cheated death and the gods didn't like that.
I don't mean why he got his punishment. I mean why he goes along with it. Why he doesn't just do like Mimi here and just.. not push the boulder.
 
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yeah... is it ever explained why he pushes the boulder if it doesn't work?
Besides various ideas like it's his only way out of Hell/Tartarus or simply that he will otherwise be whipped by the furies, my favorite interpretation is that he is simply too arrogant to admit that he can't win and that it's impossible for him to get the boulder to the top of the hill.
 
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yeah... is it ever explained why he pushes the boulder if it doesn't work?
The reason he was punished in the first place is because he thinks he's clever and can outsmart the gods. He originally cheated death by tricking Hades/Persephone.

His punishment is to roll the boulder to the top, where he'll be freed or his punishment ends or something. The gods specifically make the boulder unable to balance and roll back down, but due to his arrogance, Sisyphus believes he can get one over the gods again, he simply needs to roll it juuust right. So he keeps trying.
 

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