I’m about to see Hadestown for the sixth time in New York next week. By any measure — even my former theatre kid standards (and we’re not exactly known for our restraint) — this is excessive bordering on obsessive. I’ve tried explaining to friends why this musical moves me so deeply, why I still tear up at moments I could recite in my sleep, but somehow the words always fall short. But sixth time’s the charm, I guess, and it’s about time I gave explaining a shot. Consider this my attempt to justify what my wallet considers a questionable life choice.
Warning: Spoilers abound! Read ahead at your own risk.
An Introduction and Recap
For those still reading despite never having seen Hadestown (or those who saw it but were distracted by AndrĂ© De Shields’ magnificent sequin suit collection as Hermes), here’s what you need to know:
Hadestown reimagines the ancient Greek myth of Orpheus and Eurydice through the lens of American folk, jazz, and blues. Our story takes place in what feels like a Great Depression-era bar, where Hermes, our narrator, introduces us to a world gone sideways. The seasons are broken because the love between Hades and Persephone has grown cold.
Into this world steps Orpheus, a poor musician with an extraordinary gift, who falls in love with Eurydice, a pragmatic young drifter. While Orpheus works obsessively on reconstructing Hades and Persephone’s forgotten love song, believing it can heal the world, Eurydice faces their harsh reality of poverty and hunger.
Eventually, she chooses to follow Hades down to his industrial underworld, trading her freedom for survival. Orpheus follows to rescue her. He completes the love song, and in hearing it again, warms the frozen heart of Hades. In his mercy, Hades allows Orpheus the classical bargain — they can leave, but Eurydice must walk in the back, and he cannot turn back to look at her.
Just like the myth it’s based on, before reaching the surface, the doubt becomes too much to bear, and he looks back to make sure Eurydice is still there. In that moment of seeing her, he loses her forever. The music stops, the theater falls into a devastating silence, and he fails this ultimate test.
Echoes of Love: The Twin Relationships
I’ve always been an Orpheus critic — indeed, it seems like quite an easy task to just not turn around, dude! I never understood why this was a big deal. Hadestown is the first re-telling that contextualizes why Orpheus turned around, and it does so by masterfully interweaving his story with that of Hades and Persephone.
Hades and Persephone’s relationship is a cautionary tale of how love can calcify into possession. Their original arrangement — Persephone splitting her time between above and below — was once a beautiful compromise born of love. But as Hades’ fear of losing her grew, he began bringing her back earlier each year, trying to hold onto her longer, only to push her further away. His industrial empire itself becomes a monument to his insecurity — every wall built, every soul bought, every worker enlisted is an attempt to create something that won’t leave him.
As Orpheus and Eurydice start walking out of the underworld, we understand that Hades’ trial for Orpheus is one he’s failed so very many times before. We see that Orpheus’s bright-eyed optimism now has this veneer of doubt and fear as well — “why would she choose to follow me into the cold and dark again?”. This doubt echoes Hades’ own annual torment, watching Persephone’s train disappear into spring, wondering if she’ll truly return when autumn comes.
What makes this especially poignant is how Orpheus, our supposed hero, ultimately succumbs to the same fear that corrupted Hades. He too cannot resist the urge to look back and make sure. It’s a moment that transforms the myth from a simple story about following instructions into a profound meditation on trust and the self-fulfilling nature of doubt.
The Polysemy of Hadestown’s Plot
While Hadestown is first and foremost a retelling of a Greek myth — complete with the Fates, Hermes as our narrator, and the tragic lovers themselves — there’s another story playing in counterpoint beneath the mythological melody. Look closer, and you might see the outline of a tale about a small bar in Cancun, where business only thrives when a wealthy, kind-hearted American woman visits. But her visits grow shorter and less frequent each year, and so the workers face a choice: board the train heading north to work in the mines, trading their identities and rights for the promise of survival.
This parallel becomes unmistakable in “Why We Build the Wall,” a song that, despite being written in 2007 manages to be uncomfortably politically prescient. When Hades leads his workers in the call-and-response— “What do we have that they have not?” / “We have a wall to work upon” — we’re hearing both the timeless logic of every closed border and a very specific contemporary anxiety. Tomorrow’s headlines, set to a blues rhythm.
What’s remarkable is how these two stories — the ancient and the modern— dance together. The mythic elements give the narrative a sense of timeless tragedy. Meanwhile, the contemporary parallel grounds the myth in urgent reality — Eurydice’s choice to enter Hadestown isn’t just a mythological footnote, but a devastatingly familiar calculation made at borders everywhere.
The Metatextual, or the Audience as Character
There’s a moment in Hadestown that gets me every time. After spending two hours as a raucous, jazz-filled celebration, the show suddenly plunges into complete silence. Orpheus has just turned around, and the only sounds in the theater are occasional sniffles from the audience. The contrast is devastating — all that music, all that life, suspended in a moment of inevitable tragedy.
But this isn’t where the musical ends. Hermes steps forward to face his fallen protĂ©gĂ©, and reminds us of what he told us in the very first song: “It’s a sad song, it’s a tale of love from long ago.”
But now he adds the crucial part: “It’s a sad song, but we sing it anyway.” And as he says this, the music mellows back in. The entire cast steps in, humming, and begins to reset the stage, methodically returning every cup, every table, every chair to exactly where it was at the start. The music swells, and the musical ends just as it began — with Eurydice walking into that bar, seeing Orpheus for the first time, with all the hope and possibility of that first meeting still intact, even though we know how it ends.
This is where Hadestown reveals its deepest magic: we, the audience, aren’t just watching a story — we’re a part of it. Every night, hundreds of people gather in a theater to watch a tragedy they know will end in heartbreak. The actors perform a story where they know the hero will fail. And yet we come, they perform, and together we invest completely in the possibility that maybe, just maybe, it will turn out this time (“on this road to hell, on the rail road lines”).
In doing this, we’re not just observing the show’s thesis— that sad songs are worth singing— we’re living it. We become part of the ritual, part of the eternal cycle of telling tragic stories with undiminished hope.
This idea extends even beyond the formal end of the show. In a break from theatrical tradition, Hadestown offers one final song after the curtain call — a simple, guitar-backed melody about raising a cup to those who sing even when no one is listening.
We raise our cups, and drink ’em up,
we raise em high, and drink them dry.
To Orpheus, and all of us,
Goodnight, brothers, goodnight.
It’s a reminder that by being there, by watching and caring and hoping despite knowing the ending, we’ve participated in something larger than ourselves. We’ve helped prove that tragedies are worth telling, that Orpheus (“wherever he may be wandering / alone upon the earth”) didn’t fail completely — because his story, like all great sad songs, lives on in our collective choice to keep telling it.
The Tragedy of Everyday Life
There is nothing ambition fears more than failure. We spend so much time trying to guard against it, to ensure success, to know the ending before we begin. Hadestown is, in many ways, a gentle argument against this instinct— both within its story and within the story of its creation.
Consider this: AnaĂŻs Mitchell wrote most of these songs around 2007. Hadestown didn’t reach Broadway until 2016. Before that, it did dozens of middlingly successful performances at various theatres. Think about those nine years for a moment. Nine years of knowing in your heart that your art is worth more than what it’s currently being recognized as. Nine years of batting away the seeds of doubt that must have crept in. Nine years of choosing, again and again, to keep singing your song even when you don’t know if anyone is listening.
In this light, the show’s message takes on an almost autobiographical quality. When Hermes tells us that sad songs are worth singing anyway, when Orpheus chooses to begin his journey despite knowing the odds, when the cast resets the stage to begin again— these aren’t just plot points. They’re a philosophy about art, about ambition, about what it means to create something despite the risk of heartbreak.
Each time I watch Orpheus turn around, each time I hear the audience hold its collective breath even though we all know what’s coming, I’m reminded that the real tragedy isn’t in failing. The real tragedy would be in never singing at all, in letting the fear of the coming tragedy stop us from beginning. Hadestown tells us, through every layer of its storytelling, that the attempt itself has value— that the song is worth singing, the story worth telling, the journey worth taking, even if you might know the outcome is dire.
And so the musical itself, if it were to have a moral, tells you to sing your song — even though it might be a sad song — in spite of how it might end. It speaks to anyone who’s ever been afraid to start because they couldn’t guarantee the finish. Maybe that’s what keeps drawing me back to this show, what makes me cry every time even when I know exactly what’s coming: this reminder that the value isn’t in the ending, but in choosing to begin again anyway.