According to Greek mythology, it was not easy to descend into Hades and return. Sure, gods like Hermes and Persephone did it all the time; but for a mortal, going to the underworld and returning was a conquest of death—the greatest accomplishment a hero could achieve. Needless to say, there are very few times in Greek mythology this feat was accomplished - and yet, more than you'd think. (Sorry, Percy Jackson fans, though I am up there with you, Percy and Annabeth are not on this list).
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In his dialogue, The Republic, Plato describes the myth of Er, a man who died while at war, but whose body did not decay. When his soul reached the gates, Er was told he would be a messenger, and would let everyone know what the afterlife was like.
His tour included a scene where he witnessed souls choosing their new lives (for example, the soul of Orpheus chose the life of a swan, and the soul of Odysseus chose the life of an ordinary man); the souls then drank from the Lethe (the river of forgetfulness) and were propelled upward to their new birth. After twelve days, Er suddenly opened his eyes among the living, not knowing how he came to return to his body, and described to everyone all that he had seen in the underworld.
Orpheus was the most famous Greek bard—his music was so powerful that he once overpowered the music of the sirens. On their wedding day, his wife Eurydice died from a snakebite. Orpheus went to the underworld to speak with Hades himself, and asked if his wife could return with him. Charmed by Orpheus’s beautiful music, Hades agreed, on the condition that she follow behind him, and he not look back—if he did, she would remain.
As they made their way out, Orpheus listened to the sound of Eurydice’s footsteps so he knew she was there. Accounts vary, but in the version that I first heard, Hades tricks Orpheus by silencing Eurydice's footsteps, causing Orpheus to doubt and turn his head, and as he does, Eurydice disappears. Or, according to Ovid’s Metamorphoses, as they neared the exit, Orpheus, “fearing lest she faint…turned his eyes—and straight she slipped away.” After trying to cross the Styx a second time, Orpheus eventually returned to the world, having sworn off love.
Odysseus was the king of Ithaca, and a Greek soldier during the Trojan war who was well known for his clever mind (yep, that Trojan horse thing - his idea), and his ten-year journey home after a ten-years-long war. That story is best chronicled in Homer’s The Odyssey, which includes a visit to the underworld.
Odysseus stopped there at the witch Circe’s instructions, and made the ritual sacrifice so he could speak with spirits. One of the spirits was his father, Tiresias, who foretold what disasters Odysseus would still have to face, and that he would make it back to Ithaca, but alone and after several years. Once there, he would find Queen Penelope’s suitors taking advantage of their welcome, but he would kill them all. After speaking with other spirits, including Achilles, he returned to his ship.
Against his mother Aphrodite’s wishes, the god of love, Eros (Cupid in Roman myth) fell in love with Psyche, a reputed beauty, and took her away to a darkened palace as his bride. He warned her she could never learn his identity, but at the urging of her jealous, evil sisters, who suspected the truth, Psyche looked upon her husband’s face by the light of an oil lamp while he slept. Some of the oil spilled onto Eros’s shoulder, burning his shoulder and waking him; he reproached Psyche and flew away.
Psyche searched for Eros. A vengeful Aphrodite gave Psyche four impossible tasks; the last of these was to take a box to Persephone and ask her to put a piece of her beauty inside it. With the help of a personified tower, Psyche had sops to pass Cerberus, and money for Charon; but against the tower’s warning, she looked inside the box, which contained a death-like sleep. Healed from his burn, Eros rescued her, putting sleep back in the box, and Psyche completed her task. In the end, Zeus sanctified their marriage, and made Psyche the immortal goddess of the Soul.
Heracles (Hercules in Roman myth) is perhaps the most famous of the Greek heroes (I mean, he has his own Disney movie). The last of the twelve labors of Heracles, was the task of fetching the three-headed hell-hound, Cerberus, from the underworld. With the help of Athena and psychopomp Hermes, Heracles managed to capture Cerberus, bring him to Eurystheus, then return him to Hades. The prize for completing all the labors was immortality, which he received when his mortal half died.
What’s also notable is that Heracles actually journeys to the underworld twice. In another instance, he visited Hades to rescue Alcestis from the hands of Death.
In Euripides’s tragedy, Alcestis, King Admetus was rescued from death by Apollo, who bargained with the fates—Admetus could live if he offered up someone else in exchange. The only person willing to die in Admetus’s place was his wife, Alcestis.
On the day she was to die, while the household was mourning the loss of such a great wife, Admetus’s good buddy Heracles showed up drunk; at first he didn’t notice the bereavement of the house. When he learned of what happened, he vowed to save Alcestis as repayment for Admetus’s kindness in opening his home to him during his time of mourning. He fights Thanatos (Death) to free Alcestis, and surprises Admetus by bringing her back. Though she cannot speak for three days, she comes back alive and well.
Aeneas was a Trojan warrior, and the son of Aphrodite and a man named Anchises; before he was born, Aphrodite prophesied his destiny was to be the ruler of a new Troy. In The Aeneid, the poet Virgil chronicled the adventures of Aeneas and his crew, from their escape from Troy, to founding Lavinium, the land that would eventually become Rome.
And what would any self-respecting, years-long epic be without a stop in the fiery pits? Toward the end of this saga, Aeneas stopped in Cumae, where he met a sibyl who foretold the wars he would fight, and who became his escort through the underworld. While there, he talked with some of the dead he knew in life, including his father, who foretold of Rome and its greatness. After this visit, Aeneas settled in Italy.
The Greeks believed Theseus was a son of Poseidon; among other things, he is reputed for defeating the Minotaur and escaping the Labyrinth with the help of Minos’s daughter Ariadne. But Theseus was also lucky enough to escape Hades.
He and his friend, Pirithous, made a pact to help each other get wives; they succeeded in kidnapping Helen (who at the time was a child) for Theseus. She was rescued by her brothers, the Dioscuri (Castor and Pollux, where the gemini constellation comes from), while the pair made their next attempt. Pirithous decided on Persephone, so they ventured into the underworld, where Hades entrapped them in magical chairs. During his quest to capture Cerberus, Heracles managed to free Theseus, but was unable to free Pirithous.
Hippolytus was illegitimate the son of Theseus and the Amazon Queen, Hippolyta; as a celibate misogynist, he scorned Aphrodite and all she stood for, but worshiped Artemis, who, among other things, was a goddess of chastity. Through Aphrodite’s jealous scheming, Theseus’s wife, Phaedra, fell in love with Hippolytus. When he rejected her, she committed suicide, but left Theseus a note accusing Hippolytus of trying to rape her.
In anger, Theseus called upon Poseidon to destroy Hippolytus; through Poseidon’s curse, Hippolytus was killed in a chariot accident. In Euripides’s tragedy Hippolytus, Theseus learns the truth as his son dies, and Artemis comes to Hippolytus’s side, vowing revenge on Aphrodite. Some mythologists say it is Artemis who implores the healer Asclepius (a son of Apollo) to bring Hippolytus back to life, which he does with blood from the right side of a gordon's body.
Sisyphus, a well-known trickster, was notorious for the punishment of eternally pushing a large stone up a hill only to have it roll back down as he reached the top. But he is also notorious for his wily brain, which once enabled him to outwit Death and return home from the underworld.
Sisyphus revealed that Zeus carried off his daughter; for this, Zeus sent Thanatos to take Sisyphus to the underworld. But Sisyphus bested Thanatos and chained him; Thanatos was freed by Ares, who then turned Sisyphus over. Before he was taken away, Sisyphus instructed his wife not to perform his burial rites. Because of this, Hades did not receive the customary sacrifices, and so sent Sisyphus back to scold his wife. In one version of the story, he lived in Corinth after he returned, until he died of old age; in another, he was retrieved by Hermes and taken back to Hades. Either way, his sentence for telling Zeus’s secret awaited him.