The Odyssey: The Top 7 Trials

Odysseus and the Sea Voyage From Tartarus

Greek mythology is filled with unforgettable legends. The 12 Labors of Heracles, Jason and The Argonauts questing for The Golden Fleece, and Orpheus’ doomed journey to the Underworld to rescue Eurydice. The best of them came in the aftermath of The Trojan War, The Odyssey.

First recited by Homer in the 8th century BC, The Odyssey tells the story of Odysseus, cunning king of Ithaca, and his twenty year struggle to return home. The Odyssey is referenced throughout fantasy, though direct adaptations are rare. What gods and monsters kept Odysseus from his wife and son all those years? Let’s find out. 

Honorable Mention: The Suitors of Penelope

We can’t count The Odyssey’s final boss on the main list because Odysseus had reached his home before slaying them. But despite being a victory lap, this trial was the one he hated the most. 

Odysseus was nowhere to be found when Trojan War veterans returned home. Many citizens began thinking that he had died at sea and courted Queen Penelope in hope of becoming the new king. The Suitors spent a decade in her home, refusing to leave and taking what they wanted. That disrespect broke a sacred hospitality code called Xenia.

Penelope spent years weaving a funeral shroud and undoing the work to buy Odysseus time, claiming that she would choose a new husband when she was done. Her son Telemachus left home to search for his father, unaware that The Suitors were planning to kill him. Odysseus and Telemachus returned and signaled Penelope to give a rigged challenge for her hand in marriage.

The gods were outraged at The Suitors breaking Xenia and ordered the family to kill them all. Odysseus joined the contest in disguise and won it easily, reclaiming his bow in the process. Telemachus hid The Suitors’ weapons while they were distracted, allowing father and son to massacre them.

#7 The Odyssey: Scylla and Charybdis

Legendary heroes are hard to stop, but there are monsters that even they aren’t foolish enough to fight. This deadly duo was one of The Odyssey’s greatest threats.

Scylla and Charybdis were a pair of nymphs who were transformed into monsters. Scylla was an immortal with the upper half of a giant woman and six starving dog heads below her waist. Charybdis was a daughter of Poseidon turned into a living whirlpool, periodically drinking part of the ocean before spitting it back out.

Odysseus reluctantly sailed through their strait to return home. A witch named Circe advised him to veer towards Scylla’s lair. Six of his men were eaten by her, but that prevented Charybdis from destroying the ship.

Fun Fact: Scylla and Charybdis live in the Strait of Messina, home to a natural whirlpool and a town called Scilla. Are that town’s women immortal giants with dog heads for legs? The world may never know.

#6 The Underworld

Not all trials are physical. The most famous Greek heroes are those who entered the land of the dead and lived to tell the tale. But in The Odyssey, the hero emerged with only knowledge and grief.

Odysseus needed to know how to return home and what dangers awaited him. Circe taught him a summoning ritual and sent Odysseus to Oceanus, the edge of the world. Performing the spell allowed him to enter the Underworld.

Odysseus met several comrades from the Trojan War lamenting their deaths who advised him not to be a hero. He also learned that his mother, Queen Anticlea, had died waiting for him to return home. 

A blind prophet named Tiresias gave Odysseus the knowledge he needed, warning him of several threats and revealing that The Suitors were endangering his family. Odysseus returned to the land of the living, aware of coming dangers that he was not prepared to face.

#5 The Odyssey: The Sirens

Many of The Odyssey’s trials were caused by divine misfortune. This one was sheer hubris on Odysseus’ part.

The Sirens were birds with women’s head. Legends claim they were created by Demeter to help search for her missing daughter, Persephone. They sang a magical song to lure victims into the ocean where they would be drowned and eaten. 

Odysseus discovered an abandoned ship and realized Sirens were nearby. He ordered his crew to fill their ears with beeswax so they wouldn’t be enchanted. Odysseus wanted to hear the song himself and had his men tie him to the mast until they were clear of the Sirens. The music overwhelmed him, but the crew ensured that he survived. The Sirens drowned themselves out of shame that he had lived.

Fun Fact: The Roman name Sirenae was also used for mermaids, leading to pop culture treating them as the same thing. On the bright side, a siren song explains why mermaids are dangerous to anyone who isn’t swimming.

#4 Calypso

Odysseus made a lot of enemies in his travels, but not all of them were spurred by hunger or hatred. His longest delay during The Odyssey was born from twisted love.

Calypso was a daughter of Atlas living alone on the Ogygia islands. She found Odysseus washed up on her beach after Zeus destroyed his ship. Calypso fell in love, but Odysseus didn’t return her affection and wanted to return home. When seduction and offers of immortality failed to sway him, she used a magical song to trap him on her island for seven years.

Calypso raped Odysseus every night, leaving him to cry alone on the beach each day. His patron goddess Athena learned what was happening and convinced Zeus to intervene. He sent Odyessus’ divine ancestor Hermes to demand his freedom. Calypso accused the male gods of hypocrisy for denying goddesses the right to sleep around, but complied and gave Odysseus supplies to return home.

#3 The Odyssey: Circe

It’s strange to realize that most of The Odyssey’s greatest trials were women. Scylla, Charybdis, the Sirens, Calypso, even Tiresias spent seven years transformed into a woman. But all of them come second to this infamous sorceress.

Circe is a minor goddess who the other gods consider the most beautiful immortal. She specialized in transformation magic, turning anyone she didn’t like into animals. Circe turned Scylla into a monster because she had been a romantic rival and later did the same to a king who wouldn’t sleep with her.

Odysseus and his crew arrived on her island. A scouting party was turned into pigs after eating poisoned food that Circe had offered in a major breach of Xenia. Hermes helped Odysseus by warning him of her powers. He also gave his descendant a holy Moly flower, which would protect him from magic.

Odysseus confronted Circe, forcing her at swordpoint to heal his men and vow to the gods that she would help him. He spent a year on her island so the crew could rest, unintentionally seducing Circe in the interim. She advised him on many upcoming threats and sent Odysseus off on his quest.

#2 Polyphemus

The cyclops is one monster everyone thinks of when The Odyssey is mentioned. They appear in fantasy, video games, and the X-Men’s leader is named after them. A cyclops could be heroic or villainous, but this one was evil.

Odysseus found a cave filled with sheep and cheese. After his men ate some of the cheese, Odysseus waited in the cave so he could honor Xenia by repaying the shepherd. A giant cyclops named Polyphemus returned home and began eating his men. He thought himself above Xenia and trapped the men in his cave with a boulder so he could eat them at his leisure.

Odysseus had his men sharpen a giant club into a spear and got Polyphemus drunk on wine. Odysseus called himself Nobody so that the cyclops wouldn’t know who to seek revenge against. His men stabbed Polyphemus in the eye, leaving him screaming to his family that “Nobody has blinded me!” Odysseus and his men hid under the sheep when Polyphemus let his flock out of the cave and fled, revealing his true name as a parting shot.

#1 Odysseus

Ancient myths are funny. Half of the actions that heroes take are hellishly evil by modern standards. The greatest trial faced in The Odyssey was none other than Odysseus himself.

Odysseus’ biggest mistake was revealing his name to Polyphemus. Blinding the cyclops, stealing his flock, and allowing him to live was considered a fate worse than death. Polyphemus prayed for revenge against Odysseus. Poseidon, god of the sea and Polyphemus’ father, was more than happy to avenge his son. Poseidon’s storms battered Odysseus’ ships for years until a final voyage and sacrifice appeased him.

Secrecy was another problem. After spending time with King Aeolus, Odysseus was given a bag containing three of the four winds so that the only wind blowing would send him home. He kept the bag hidden and didn’t tell his crew what was in it. Odysseus stayed awake for days, finally falling asleep when Ithaca was in sight. The crew opened the bag they thought was filled with treasure, blowing the ship far away home.

Odysseus’ pride, secrecy, and other flaws led to second in command Eurylochus leading a mutiny. While hunting on Helios’ island, the crew killed some of the Titan’s sacred cattle. Zeus sent a lightning bolt that destroyed their ship and killed everyone except for Odysseus, who awoke on Calypso’s island.

Which of The Odyssey’s trials do you think was the most legendary? Which will be adapted best in the 2026 movie? Tell us in the comments.

Image: Matt Damon in The Odyssey. © 2025 Empire

Jared Bounacos

Jared Bounacos has written for Movie Rewind since 2016.