Orpheus was a bard, a singer of great renown, son of the Muse Calliope and also the King of the Cicones, a tribe that lived in the Rhodope Mountains in Thrace (part of what is now Bulgaria). They say that he was the first to master the lyre that Hermes made upon the first day of his birth, a gift from his first teacher Apollo who taught young Orpheus to play upon the slopes of Mount Parnassus. None have played the lyre so perfectly since Orpheus. His voice, trained by his dear mother Calliope, was so perfect in pitch and tone that none could hear it and not be moved and the songs that he created and performed with his two instruments, voice and lyre, charmed birds from the trees, tame beasts and even coaxed the trees to dance. He was also a seer and a servant of the Gods Apollo and Dionysus and he taught his people to honor them and keep their feast days.
It came to pass the Orpheus met and fell in love with a maid who could dance as well as he could play and she was called Eurydice. She was charmed by his singing and he by her dancing and they loved each other in form and speech as well. Two people never were so in love as Orpheus and Eurydice and on their wedding day all of the Muses and the naiads came and there was much feasting and singing and dancing. Eurydice was as lovely as ever in her wedding dress with ivy in her hair dancing among the naiads until she appeared to stumble and fall! In her joy she hadn't noticed a small snake resting on a rock and she'd stepped upon him and the poor snake in his fright had in turn bitten her on the ankle. And so it was that poor Orpheus watched his dear bride die of the poison bite before she ever had the chance to be his wife.
After Eurydice's death all days were the same to Orpheus. He rose in the morning and played her an epitaphe. He wandered through the streets singing a dirge he wandered the hills lamenting and his requiem filled the night. All who heard them were moved to pity. Women went about with tears streaming down their faces, men became too depressed to work, the birds ceased singing in favor of Orpheus's lament and even the trees had no interest in fruiting, which is just as well because the bees had lost all interest in pollinating them.
Finally, Orpheus's mother Calliope called him to her and said, "My son, you must put aside this constant weeping. You are bringing the rest of the world down with you. What can we do to ease your pain?"
"Nothing." He declared, "Will ease my pain save to hold Eurodyce in my arms once more."
"Don't be unreasonable and wish for the impossible. You must come to terms with reality." His mother advised. "No one who enters the realm of Hades returns. Life is for the living."
"I will not forget her." He declared. "Perhaps I will go and get her."
Now Calliope wasn't sure this was such a good idea, but at least it gave the poor boy something to do, so she said, "Then go down to the Kingdom of Hades, He and His Queen are kin to us both. Perhaps they will grant an exception to their rules just this one time, for love of family." And she told him the way and he went.
He walked a long way until he came to the grim path that leads to the place where the river Acheron(woe) meets the river Cocytus(lament). There he met the ferryman Kharon. Kharon was disinclined to ferry him across, but that got Orpheus lamenting again and Kharon, tears soaking his tattered robe, finally agreed to ferry Orpheus across if he would just stop singing!
On the other side, Cerberus, the great three-headed dog of Hades, greeted Orpheus with suspicion. He crouched down and growled, blocking the way before the gates of the underworld. But Orpheus had charmed great beasts before with his little golden lute and Cerberus was not so much different from other beasts. Soon he was quite calm, enchanted with Orpheus's song, and let Orpheus pass unharmed.
For many days Orpheus walked across the colorless plains of Asphodel among crowds of the dead. Some were walking purposefully, like he was, toward the palace of Hades which could be seen in the distance. Others wandered aimlessly, lost, confused, crying out for their loved ones. The din was terrible but still he marched on and soon brought out his lute again to cheer himself and the wailing of the lost souls was quieted.
Finally, he came to the Plain of Judgement where those who are too wicked to enter the presence of the Dread Lord and His Queen are turned away and cast into Tartarus and where those whose names are to be remembered with honor for all time are sent instead to the Ilses of the Blessed. There the three judges Minos, Radamnthus and Aeacus saught to challenge him but when they heard the music of his lute, they agreed that their King and Queen must hear it as well and they sent him in to to see Them right away.
Orpheus came before the thrones of Hades and Persephone and bowed low. "I am your cousin, the son of Your half-sister, my Queen and the grandson of Your brother, Oh King. Please attend to my boon and accept the offering that I have for you in exchange."
"I have come to retrieve my lost love. And if you should refuse me, then I should stay, for there is no life without her."
Hades and Persephone found it quite amusing that this young upstart should expect them to change the rules for him, even if they were family. Were they themselves not subject to these rules? Persephone smiled gently and said most politely, "You are welcome to stay with us cousin."
"Then let me entertain you." He said and brought forth his lute and began to play and sing. He sang a lovely song praising the fairness of Persephone and the strength of Her Lord Hades. Then he sang a love song that he had written for his bride and played for her on their wedding day and the song was so lovely that Sisyphus was compelled to cease his labors and sat upon his rock to listen. Then he sang the lively tune that she'd been dancing to when she died and Hades' long fingers, resting on the arm of his cold stone throne, began to tap the rhythm. Then Orpheus began to sing of his sorrow for his lost love and he sang and he sang and soon Persephone's face shone with tears, even the Erinyes wept and finally Hades put up his hand that he should stop.
"Cousin, you have caused trouble in my kingdom. You fill us with sorrow so that even the strongest among us may be rendered weak if you continue. Go forth now and make your way back home. Trust that your bride will follow and do not look back until you are home."
Overjoyed, Orpheus prepared to leave at once. He rushed out of the castle, practically dancing with joy. And he did not look back. He waved cheerfully to the judges on the plain of judgement and he did not look back. He sprinted across the fields of Asphodel and he did not look back. Cerberus yeilded to him as he approached, but he didn't stop to give the dog a kind word but rushed right up to Kharon to procure transport for himself and his wife back to the land of the living. He sang with joy and laughed and as he stepped onto the ferry he turned around to ensure that his Eurydice had stepped up too. And all he saw was a whisp of a shadow fluttering and disappearing back into the underworld and he heard a small voice whisper, "Alas and goodbye my love."
He tried to go back, but the ferry had already launched. Kharon restrained him and Cerberus snarled viciously from the shore. Soon Kharon deposited him back in the land of the living and he quickly moved his ferry away ignoring his pleading. Orpheus launched again into a dirge and he sang for days not eating or sleeping but nobody heard him except the souls of the dead who had no more power in the situation than he did.
Finally, he made his way back home. He never sang or played again and he foreswore thereafter the love of all women, and the worship of all Gods save Apollo. Some time later he was killed by Manaeds, wild women of Dionysus. Some say because he rejected their advances, others say because he rejected his former God Dionysus. Either way, he is together with his Eurodyce now.
Adapted from Ovid's Metamorphosis and other sources.