Of all the cruel punishments the Greek gods bestowed on humans (and one another), the punishment of Sisyphus has to be the worst.
Sisyphus was the king of Ephyra and the son of Aelius (ruler of the winds and son of Poseidon…the guy has some serious lineage behind him).
He was also a prideful, deceitful, murderous ruler; not only was he a chronic liar (deceiving both gods and humans), but he killed travelers and visitors for fun in his own kingdom.
Basically, Sisyphus was a real prick.
Apparently, after one too many deceitful and murderous acts, Zeus decided enough was enough and condemned Sisyphus to an eternal punishment. Except this wasn’t any old punishment. Zeus crafted something uniquely horrible for Sisyphus.
Zeus condemned Sisyphus to push a large bolder up a steep hill.
Difficult for sure, but not the worst thing in the world (or underworld), right?…
Except, like all good Greek myths, there was a catch.
Zeus enchanted the bolder.
Anytime Sisyphus came close to the top of the hill with the bolder, it would slip through his hands, rolling all the way back down to the bottom.
No matter how Sisyphus approached the challenge, his effort was futile.
An eternity of useless, infuriating effort with no payoff.