Sisyphus was born to Aeolus, the king of Thessaly who had power over the winds, and his wife Enarete, though some said his mother was the nymph Kretheis. He had several brothers, including Salmoneus, the king who had mocked Zeus by driving a chariot with bronze kettles attached to make thunder, and who was struck dead by a real thunderbolt for his impiety. Sisyphus learned from his brother's example, but he did not learn caution. He learned cunning. He founded the city of Ephyra, later called Corinth, on the narrow strip of land that joined the Peloponnese to central Greece, and he made it rich by controlling the trade that passed between the Ionian Sea and the Aegean. Ships that did not want to sail around the stormy southern cape of the Peloponnese could drag their vessels across the isthmus on a paved road called the diolkos, and Sisyphus taxed them for the privilege. The city grew wealthy, and Sisyphus grew powerful, but wealth and power were never enough for him. He wanted to live forever, and he was prepared to deceive anyone, even the gods, to achieve it.

The first great trick came when Zeus, the king of the gods, abducted the nymph Aegina, the daughter of the river-god Asopus, and carried her off to an island that would one day bear her name. Asopus searched the earth for his daughter, and Sisyphus, who had seen where Zeus had taken her, offered to tell the river-god in exchange for a spring of fresh water for his city. Asopus agreed, and Sisyphus revealed the secret. Zeus was furious. He sent Thanatos, the personification of death, the daimon who ended the lives of mortals when their time had come, to fetch Sisyphus to the underworld. But Sisyphus was ready. When Thanatos arrived with his chains, Sisyphus asked him how the chains worked. The spirit of death, proud of his craft, demonstrated by fastening the chains around his own wrists. Sisyphus, quick as a snake, tightened the chains and bound Thanatos fast. Death was trapped, and for a time the world stopped dying. The old grew older without end, the wounded could not find release, and the gods themselves were inconvenienced by the backlog of souls. Finally Ares, the god of war, was sent to free Thanatos, for war without death was meaningless, and Sisyphus was dragged to the underworld.

But Sisyphus was not finished. Before he died, he had given his wife Merope strict instructions: when his body was laid out, she was to leave it unburied, to throw it into the public square without funeral rites, to deny him the coins for the ferryman Charon and the libations that eased the passage of the dead. Merope, who loved her husband or feared him too much to disobey, did as he asked. When Sisyphus arrived in the house of Hades, he stood before Persephone, the queen of the dead and daughter of Demeter, the goddess of the harvest, and complained bitterly. His wife, he said, had disrespected him in the most terrible way. She had left his body unburied, denied him the proper rites, treated him worse than a slave. He begged Persephone to let him return to the world of the living just long enough to punish Merope and arrange a proper funeral. Persephone, moved by his apparent grief or perhaps simply amused by his audacity, granted his request. Sisyphus walked out of the underworld, reclaimed his body, and simply refused to go back. He lived on in Corinth for many more years, laughing at the gods who had thought they could contain him.

The gods would not be mocked forever. Hermes, the messenger of the gods, whose cunning matched Sisyphus's own, was sent to fetch him, and this time there was no trick, no ruse, no escape. Sisyphus was dragged back to the underworld and brought before the judges of the dead, who weighed his crimes against his virtues and found him wanting. He was condemned to Tartarus, the deepest pit of the underworld, the prison of the Titans and the worst sinners in Greek myth. His punishment was devised by the gods themselves, a labour so perfectly suited to his character that it became a symbol for all time. He was set to roll a massive boulder up a steep hill, a task that required all his strength and all his cunning, for the hill was treacherous and the boulder was heavy. But every time he neared the top, the boulder slipped from his grasp and rolled back down to the bottom, and Sisyphus had to walk back down and begin again. The punishment was not the labour itself but the hope that always preceded the fall, the moment when he believed he might finally succeed, followed by the inevitable collapse. It was a punishment designed for a man who had always believed he could outsmart the universe, and it worked because it made him the architect of his own endless frustration.

In life, Sisyphus had also been the father of Glaucus, who would become the father of Bellerophon, the hero who tamed the winged horse Pegasus and slew the Chimera. But the family line was cursed. Bellerophon, after his great deeds, tried to fly to Olympus itself and was thrown from Pegasus by Zeus, becoming a crippled wanderer. The curse of Sisyphus's cleverness seemed to pass down through the generations, a reminder that the gods do not forgive those who make them look foolish. Sisyphus himself, in some traditions, was also the father of Odysseus, though this was a less common genealogy and one that the poets of the Odyssey did not accept. The connection was made because both men were famous for their cunning, but Odysseus, for all his tricks, never tried to cheat death itself, and that may be why he was allowed to return to Ithaca while Sisyphus rolled his stone forever.