- Orpheus's Heroic BSoD when Persephone has to leave for Hadestown early. He keeps talking about how unfair it is for the people above.He came too soon
He came for her too soon
It's not supposed to be like this
- Eurydice leaving for Hadestown. She is really only doing it out of practicality and is torn up about leaving Orpheus for it, but can't ignore that she's starving to death while Orpheus can't provide.
- When Orpheus and Eurydice reunite, he says, "I'm to blame" for not hearing Eurydice calling after him before Hades took her away. Eurydice says he isn't, and tells him to run when Hades appears.
- Hades and Persephone's deteriorating marriage. They both still love each other, but their different desires are tearing them apart. Hades is focused on solely materialistic items and drives his slaves to constantly build impressive machinery hoping that it will win Persephone over. Persephone meanwhile is horrified at the slave labor and the dying upper world under her husband's hand and just wants them to go back to older times when they were happy.
- The reason why Hades keeps coming for Persephone sooner and sooner every spring: he's terrified that one day she won't come back.
- The look on Persephone's face during "Why We Build the Wall" as she sees Eurydice enter Hadestown and realizes just how much she's stood by and let Hades do.
- "If It's True" is Orpheus's BSoD Song after the Hadestown workers beat him up on Hades's orders. He lays on the ground, asking if this is how the world really is. Just as he's about to leave, the workers start echoing his song, giving him the resolve to stay and fight for Eurydice, with the power of his music.
- "Epic III" has heartbreaking lyrics as Orpheus wonders what's become of Hades and the love he and Persephone shared, and it ends with Hades singing the old song as he and Persephone dance. With all the buildup and vulnerability, it makes it twice as heartwrenching when Hades still isn't sure he can let them go afterward.And what has become of the heart of that man
Now that the man is king?
What has become of the heart of that man
Now that he has everything?
- Hades's voice when he sings his song is breathy and weak. You can tell that he's not just overcome with his love for Persephone, he's now realizing that despite how head-over-heels he was the very moment he laid eyes on her—so infatuated he couldn't even speak, and could only sing—he's allowed their marriage to be years and years and years of misery.
- In the final repetition of the chorus, Persephone reaches out for Hades to take her hands. He does...and right as their hands touch, the signature red carnation blooms in his fingers. Hades has fallen head-over-heels in love with Persephone all over again, and the realization makes Persephone weep.
- Even if we do know how the myth ends, it's still heartbreaking knowing that Orpheus looks back at Eurydice and loses her to Hadestown again. In the staging, it is particularly wrenching; he turns around and she gasps loudly. They say each other's name, knowing it's the last time they'll talk. Then the stage platform lowers her out of his sight, where he loses her to the underground. Orpheus falls on his knees with a My God, What Have I Done? expression and stays there, staring into the world below as Hermes launches into a Dark Reprise of "The Road To Hell". Orpheus doesn't stand until Hermes restarts the tale and resumes where he was at the beginning of the play.
- At the start of "The Road to Hell (Reprise)," Hermes is quiet, breathing raggedly before weakly muttering, "A'ight..." and launching into his narration. The poor man sounds like he's about to break down sobbing.
- The post-curtain call song, "We Raise Our Cups," has the dead mourning the living as Persephone, Eurydice, and the company toast Orpheus, wherever he is, and hope their music gives him comfort. Even Hades joins in.
- There are many hints that Hermes is telling the tale over and over, trying various combinations and variations to save Orpheus and Eurydice. Nothing works; each time, Orpheus turns around too early and loses his wife. Worse, all of the characters are put through the same motions and suffering. Persephone and Hades are doomed to never reconcile and Eurydice is fighting against the cold and hunger. Hermes means well but not even a Great Depression incarnation of a Greek god can do good.
Tear Jerker / Hadestown