Hermes could say, with confidence, that he hadn't meant to get so involved. At first it was just a job to him, a simple job he'd done for millennia—conduct the newly-dead down to Hadestown, and, under the Lord of the Dead's watchful eye, entice any wayward souls interested in a lifetime of hard work for little pay.

Not that he'd told them that, of course. Hermes reflected on his past actions with a measure of shame, remembering how tempting he'd made the offer sound: Free bed and board, steady work, everyone with equal pay. It was a practiced sales pitch, and one that nearly always worked, but the time it didn't was the time he took an interest.

The boy, Orpheus, had seen through his tricks, cut down every offer he made with confidence. But his girl, Eurydice, was more easily swayed, tired from a life of poverty, and Hermes had sent her down the first time without regret. The boy would arrive to Hadestown on his own time; mortals always did. But when Orpheus had taken him by the suit collar and nearly throttled him demanding to know where she was and how to get her back, well, Hermes had to admit to being intrigued. He snuck the boy on the next car out, a living boy next to incoming souls like a free surprise in a cereal box, and when Hades sensed his presence and his song Hermes was quick to provide excuses.

Running both sides had its benefits, and if his boss was suspicious, well, nothing he could do. Psychopomps in this modern world were hard to come by, and he'd earned his trust over millennia. Hermes watched and waited as Orpheus made his way to Hadestown and was soon found and beaten by the security guard, Cerberus, her reputation as ferocious as the dog she shared her name with. She'd hauled him before Hades and his wife, and while Hades was unmoved when Persephone stood up for the couple and begged him to let them go, Orpheus's song quickly changed hearts and minds.

A deal was made, and for all that had changed since, and all that would surely still change, its conditions were the same. Orpheus would go, Eurydice would follow behind, and if he turned back, that was it. Hermes accepted his role in events with a nod; Hades had put him in charge of ensuring events proceeded as planned. There was always a catch to his deals, the messenger god knew, and that was just how things were.

But when Orpheus did turn, and lost his wife, and his songs were drowned in laments and wailing—well, something in Hermes changed then too, even as he took Eurydice by the arm and led her down below per the agreement. It was a while after, when he stopped by an aboveworld bar and found Persephone drowning her sorrows with the broken boy, as he cursed the Fates and their tale, that he realized what it was he was feeling.

He felt sorry for Orpheus and Eurydice.

Hermes' first instinct was to suppress it. A man in his line of work couldn't get attached, couldn't think of subverting the natural order of things. And when the story reset itself, the snake eating its tail to start it all again, he was careful to detach himself from the lovers as much as possible.

He was still conductor, still had his job, but he didn't tempt Orpheus away this time, only listened as the Fates sang of pockets weighted with gold and ambrosia on every pair of lips. Eurydice was still intrigued, still listened all too well, and he sent her down quietly. Orpheus soon found her missing, but the train had long gone by the time Hermes approached. If the boy wanted his love back, he was going to have to work for it.

He gave him directions this time, how to take the long way down, how to avoid the tricks and traps Hades had set for trespassers. Orpheus made it there with difficulty, hiding out in the Queen's speakeasy until they were discovered. There was still a fight, still an argument between gods, still a last, desperate chance for Orpheus and Eurydice's survival.

As before, the boy turned at the last, dooming Eurydice once more. And Hermes found himself feeling, if possible, worse than before. Detachment had, it seemed, only made things harder, both on the lovers and himself. He questioned why he felt this way, why two souls out of millions had stirred what was left of a conscience in him, but the why didn't matter so much as what he would do next.

The next few times he involved himself more in their lives. Told the tale with gusto, introduced the players and watched as the story shifted and changed over time, accommodating his new role like it had been waiting for him. While not quite the life of the party, Hermes sang and danced with Orpheus, Eurydice, and the rest when able, then rested on the sidelines to wait for what he knew was coming. The train waited, always waited, and could not be delayed forever.

The storm was a recent addition, driving Eurydice out of Orpheus's hands faster than an empty belly, and Hermes idly wondered if the Fates wrote it in to compensate for his advice, or if things had simply deteriorated that much between Hades and his Queen. When Hades showed Persephone what he'd done to the Underworld, modernizing it, industrializing it before their eyes with the 'help' of his workers, Hermes suspected the latter. It wouldn't do to anger the Fates, anyway.

Orpheus, full of confidence and eyes shining bright with hope, bravely took up the challenge of rescuing his love. His bravado was infectious to the point that Hermes thought he just might make it this time.

But, as ever, Orpheus turned.

And when the tale reset again, by now almost too many times to count, a new wrinkle in the story presented itself. Hermes' friendship with the muse Calliope had gone way back; he enjoyed her songs, she his company and occasional tale. But now, before the story could properly start, she arrived on his doorstep with a child in tow. His name, she explained, was Orpheus.

At the name Hermes stood thunderstruck, and more so when Calliope explained she couldn't keep him. Times were hard and only getting harder, and she knew he owned a bar, had a decent-sized salary from Hades. He could provide for him in ways she couldn't, and when Orpheus turned his face up to look at him, Hermes saw a difference in his eyes from past loops.

The boy Orpheus still sparkled with intelligence and song, but there was a naivety as well, and a quiet kindness. In his eyes, Hermes could see how the world could be in spite of the way it was, and he nodded to Calliope when she asked if he could take him.

Under Hermes' wing, Orpheus grew. He had never been involved to this degree before, and every little decision set him on edge even as he knew the story had to progress to a certain point, regardless of how. By the time he was a young man Hermes had grown used to his idiosyncrasies, gave him a job cleaning tables to earn an income, and when he saw the girl sitting alone at a table Hermes knew before Orpheus did that it was love at first sight.

He hadn't been lying before when he said he wasn't kind. Orpheus and Eurydice, their struggles and love, had made him kind. Hermes could scarcely imagine wanting to harm either of them on purpose, now, and when the storm clouds rolled in he did his best to make Orpheus see what was happening before his love was swept away in the wind, down to Hadestown with the rest of the working dead.

He gave the directions; he watched and waited with bated breath as Orpheus took the long way down. Watched as the boy who was like a son to him sang before Hades and Persephone even while beaten and bleeding, as the girl who was like a daughter to him saw her fate decided. Watched with mixed horror and sorrow as Orpheus, seeing how the world could be at its worst, turned around and lost Eurydice once more.

After all this time, it seemed some things refused to change.

By now he knew how the story ended, whether observer or player in the old tale. But, like Orpheus, searching for love with a lyre and a dream, like Eurydice, searching for a better life and a steady hand to hold, even like Hades and Persephone, searching for ways to bring back their old romance and be happy once more—Hermes refused to give up.

A dear friend, more like a son than anything, had taught him that. And so, when Orpheus turned, Hermes set the tale spinning back without a second thought. Maybe it'd turn out this time, and if not, he'd try again.

He was involved in the story now, a part of it til the end, and Hermes wouldn't have it any other way.


For readers who may be confused by the beginning of the story, in very early Hadestown shows circa 2006-2007, Hermes was a more direct accomplice of Hades who tried to tempt Orpheus down to Hadestown, but still helped him get there when needed. Cerberus the security guard is also from this time period; she was played by Sara Grace, and her role was deleted when the workers were introduced.