A Greek kig who was condemned to hell by having to roll a rock up a hill only for it to roll back down also someone who does the same thing over and over again
Selena is such a Sisyphus with her boyfriends, it's a new one every month
by Word doctor 6990 June 15, 2017
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Edging until the end of time (or for an extreme amount of time).
A: I did sisyphus edging for the entirety of No Nut November.
B: Gee willikers, how do you not have cock burn?
by hubertg October 15, 2020
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From "Back to the Future" to describe the fate of Biff Tannen, marked by his repeated, failed attempts and subsequent punishment for his evil transgressions, muchly similar to Donald Trump.
We watched "Back to the Future" so many times, only to mock The Sisyphus of Biff.
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When you are working really hard at something and getting nowhere
I took this girl out, bought her dinner, and talked her up 3 times and got no booty, I am really Sisyphusing it
by Uphill ice skater March 10, 2022
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