The Worst Things That Happened To Odysseus, Ranked

Odysseus faced numerous monsters, including the Cyclops Polyphemus. Odysseus and his 12 companions arrived at "the land of the Kyklops race," described as, "arrogant lawless beings who leave their livelihoods to the deathless gods and never use their own hands to sow or plough." They entered Polyphemus's cave while the one-eyed creature was tending to his sheep and goats. 

Once in the cave, Odysseus and his men helped themselves to the food they found, and when Polyphemus arrived, he blocked them from leaving. He asked who Odysseus and his men were, and while they were explaining, Polyphemus,

stretching his hands towards my companions clutched two at once and battered them on the floor ... their brains gushed out and soaked the ground. Then tearing them limb from limb he made his supper of them. He began to eat like a mountain lion, leaving nothing, devouring flesh and entrails and bones and marrow.

Polyphemus's brutality continued into the next day and only ended after he became so drunk that he lost consciousness. Odysseus then took a stake and "thrust it into the giant's eye," blinding him so the remaining men could flee.

Polyphemus didn't endure his wound quietly and roused the attention of his fellow Kyklopes. They suggested he "say a prayer to [his] father, Lord Poseidon," which Polyphemus did. As a result, per the Odyssey,

Poseidon the Earth-Sustainer [remained] stubborn still in his anger against Odysseus because of his blinding of Polyphemos (Polyphemus), the Kyklops (Cyclops) ...  Ever since that blinding Poseidon has been against Odysseus.

Odysseus experienced Poseidon's wrath for the rest of his journey, constantly "wandering far from his native land" at the Sea-God's behest.

Despite the Odyssey's assertion that Odysseus returned home, retook power, and lived out his days peacefully, there are other myths associated with his final days. In the remaining fragments of The Telegony, Odysseus remarries after the death of Penelope, taking Callidice, queen of the Thesprotians as a bride. When the Thesprotians go to war, Odysseus leads the charge and ultimately paves the way for his son with Callidice, Polypoetes, to rule Thesprotians.

Odysseus returned to Ithaca after his time with the Thesprotians, only to have his domain attacked by Telegonus - one of the sons he had with Circe. When,

Odysseus comes out to defend his country, [he] is killed by his son unwittingly.

Telegonus took the body of Odysseus to Circe, the sorceress, to bring him back to life. But, as a later tradition explained, Odysseus would die again after Telemachus (his son by Penelope) died at the hands of his wife, Cassiphone (Odysseus' daughter with Circe) after Telemachus killed Circe. That's when Odysseus died - again - from grief. 

When Odysseus and his men arrived in the "house of Hades" - the Underworld - it was to hear a prophecy from the blind prophet, Teiresias. While there, Odysseus faced several ghosts. One was Elpenor, a fallen member of his group, who met a drunken death on Circe's island:

I was lying asleep on the top of Circe’s house, and never thought of coming down again by the great staircase but fell right off the roof and broke my neck,

Odysseus promised Elpenor he would go back and give him a proper burial before moving on to find the ghost of his mother. Odysseus' mother told him about his wife, his son, and their lives without him, as well as her own death from grief. Odysseus "tried to find some way to embrace my poor mother's ghost," but was unable to do so. 

More ghosts lined Odysseus' path to Teiresias as their fates and his past confronted him. By the time he received the prophecy from Teiresias and was able to leave the Underworld, it was only as "many thousands of ghosts came round me and uttered such appalling cries."

The misuse of the winds given to Odysseus and his men by Aeolus preceded their arrival at the harbor of Telepylus. A city where the Laestrygones lived, Telepylus was "land-locked under steep cliffs" so Odysseus told his ship captains to sail into the harbor while he remained "moored... at the very end of the point."

Odysseus had twelve ships at this point and the crews from the eleven ships that went to Telepylus went ashore. There, they met the daughter of Antiphates, a Laestrygonian. Antiphates directed the men to her father's home and, once there, as Odysseus relays in the Odyssey:

[H]e set about killing my men. He snatched up one of them, and began to make his dinner off him then and there, whereon the other two ran back to the ships as fast as ever they could. 

It was too late for Odysseus's men, however, because Antiphates called forward "thousands of sturdy Laestrygonians" who were "ogres, not men." Those ogres,

threw vast rocks at us from the cliffs as though they had been mere stones, and I heard the horrid sound of the ships crunching up against one another, and the death cries of my men, as the Laestrygonians speared them like fishes and took them home to eat them. 

Odysseus and the men on his one remaining ship fled so that they wouldn't "fare like the rest." Unfortunately, when all was said and done, the men "were thankful enough when we got into open water out of reach of the rocks they hurled at us. As for the others, there was not one of them left."

Odysseus lost nearly 600 men at the hands of the Laestrygones, adding to the 72 he lost while at Ismarus and the six Polyphemus ate. As the first stop on the journey, Ismarus was home to the Cicones and, after Odysseus and his men sacked it, the Cicones countered with an attack that killed six men from each of his dozen ships. 

After escaping Scylla and Charybdis relatively unscathed, Odysseus and his men arrived at the Island of Thrinacia. Also known as the Island of the Sun, this was the home of Helios, the god of the sun. On the island, Helios tended his sacred cattle and sheep and, as a result, Odysseus had been warned about landing there by Teiresias when he was in the Underworld:

If you leave these flocks unharmed and think of nothing but of getting home, you may yet after much hardship reach Ithaca; but if you harm them, then I forewarn you of the destruction both of your ship and of your men.

Odysseus was willing to heed the advice and made the men promise not to harm the sheep or cattle. They violated this once they arrived, unwilling to stay away from animals:

Now the cattle, so fair and goodly, were feeding not far from the ship; the men, therefore drove in the best of them, and they all stood round them saying their prayers ... When they had done praying they killed the cows and dressed their carcasses; they cut out the thigh bones, wrapped them round in two layers of fat, and set some pieces of raw meat on top of them. They had no wine with which to make drink-offerings over the sacrifice while it was cooking, so they kept pouring on a little water from time to time while the inward meats were being grilled; then, when the thigh bones were burned and they had tasted the inward meats, they cut the rest up small and put the pieces upon the spits.

Once Helios was told about this, he went to Zeus and demanded vengeance under threat of never shining again without it. Zeus then,

let fly with his thunderbolts, and the ship went round and round, and was filled with fire and brimstone as the lightning struck it. The men all fell into the sea; they were carried about in the water round the ship, looking like so many sea-gulls, but the god presently deprived them of all chance of getting home again.

Odysseus was the lone survivor. As the only person left, Odysseus was adrift at sea until he washed up on the shore of Ogygia. There, the nymph Calypso found him and made Odysseus her prisoner for seven years.

When Odysseus and his men faced Scylla - the six-headed monster - and navigated the whirlpool Charybdis, they were traversing a narrow passage between the two. 

Odysseus had been warned by Circe about this part of the trek, telling him that he must stay closest to the side upon which Scylla perched. This was because Charybdis churned and sucked down whatever was nearby three times each day. When Odysseus finally arrived to take on the deadly pair, he followed Circe's guidance as well as he could:

[W]e entered the Straits in great fear of mind, for on the one hand was Scylla, and on the other dread Charybdis kept sucking up the salt water. As she vomited it up, it was like the water in a cauldron when it is boiling over upon a great fire, and the spray reached the top of the rocks on either side ... We could see the bottom of the whirlpool all black with sand and mud, and the men were at their wit's ends for fear. While we were taken up with this, and were expecting each moment to be our last, Scylla pounced down suddenly upon us and snatched up my six best men. 

Odysseus was helpless to do anything to save his men. He explained,

I was looking at once after both ship and men, and in a moment I saw their hands and feet ever so high above me, struggling in the air as Scylla was carrying them off, and I heard them call out my name in one last despairing cry ... Scylla land[ed] these panting creatures on her rock and munch them up at the mouth of her den, while they screamed and stretched out their hands to me in their mortal agony. This was the most sickening sight that I saw throughout all my voyages.