I see a lot of people online saying that Orpheus (Hadestown specifically) looks back because he loves Eurydice so much, that there isn't a world in which he doesn't look back, because the kind of man who wouldn't look back is not the kind of man who would go after her in the first place, etc. It's inevitable because of the strength of his love. But I don't see that as being the whole picture. Textually, it is explicitly his doubt in himself, and in the narrative of his life, that makes him look back: "Doubt Comes In", and he wonders, who is he that Hades would let him win? Who is he that Eurydice would follow him through the dark? Orpheus used to have a very simple, naive view of the world and his place in it. He was single-minded. At the beginning he tells Eurydice he's the man who is going to marry her because...well, that's how the story should go, and he is a poet first and foremost. Then, when he meets Hades, he is confronted by what Eurydice did and what the world is really like. He is shattered by the realisation that Eurydice wasn't just a simple, "pure" victim, but that she signed her life away. He is beaten down and loses faith, he goes into "Is this how it is?" after he's literally already done the impossible by reaching Hadestown on foot. He should have proven his abilities to himself by this point, but things aren't going the way they are supposed to and he doesn't know who he is anymore. He isn't just a boy in love with a girl who sings a song to bring back spring: he's a boy who didn't look back when he should have the first time when she called his name; she's a girl who chose her immediate needs over his grand ideals. His faith in a world where they make it back together is broken. He looks back because he doesn't trust himself or the narrative that he's found himself in. It's even more heartbreaking to me, because the Orpheus he was at the beginning of the musical might not have looked back, but that version of Orpheus doesn't make it out of the Underworld.
And to top it all off, the version of Eurydice from the beginning of the musical, before love softened her hard edges and made her trust him, probably wouldn't have followed Orpheus out of Hadestown. Eurydice really does trust him to get her out, because she's looking for the Orpheus she used to know and she's seen the power of his song and worldview.
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