Sisyphus is immune to damage, though he will respond if Zagreus takes a swing at him or Bouldy regardless. He can only appear once during each escape attempt. During these meetings, Sisyphus will offer Zagreus a choice between, 50-55 or 100. Zagreus can sometimes encounter Sisyphus taking a break from boulder-pushing while making his way through Tartarus. He refers to his boulder as ' Bouldy', treating 'him' as a friend and confidante, and speaks quite casually with Zagreus, whom he typically calls 'Prince Z. In spite of his never-ending punishment, Sisyphus is generally good-humoured and polite, having had ample time to reflect on his deeds in life. The Furies - and Megaera in particular - torment him as he attempts to push the boulder, though with Zagreus' recent escape attempts, they appear to be slacking on this particular duty. His punishment is to roll a boulder up a steep hill the boulder, however, always rolls back down the hill before he reaches the top, despite his best efforts. He succeeded twice, each time only temporarily before the consequences caught up with him.

Sisyphus is a former king sentenced to an eternity of punishment within Tartarus for attempting to cheat death. Within the depths of Tartarus reside the most wretched of all the shades who linger for eternity within the Underworld, whose Lord and Master is especially unkind to those attempting to cheat death.

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