No matter how many times I listen to it, hearing the introductory chords to “Tailor” by Anaïs Mitchell is always like biting into oven-warm, homemade chocolate cake. There is decadent richness in the reverb on her acoustic guitar, warmth in the standup bass mirroring the guitar’s low notes, and comfort in the way the familiar-but-not-banal chord progression sounds so right.

I feel supported by these echoing major chords, lifted up from underneath, until Mitchell’s vocal begins. Underneath Mitchell’s voice, the dominant major chord becomes a seventh chord and the warm cocoon of the introduction suddenly slips away. Her unmistakable timbre is surprisingly breathy as she sings the dissonant high note along with the guitar. It introduces a hint of heartache; if the first chords evoke the warmth of childhood, the dissonant chord feels like looking back on it knowing you can’t return.

Mitchell’s voice is high, and it sounds almost childlike here. This quality simultaneously sparkles over the song’s melancholy and adds to its shroud of nostalgia. Mitchell sings of letting a lover create her self-image, of mourning when he leaves, and of wondering how to define herself in the remaining vacuum. It’s a gentle, honest, and heartbreaking story. Vocally, I can only compare her to some of the legendary ladies of folk and fountry like Emmylou Harris and Gillian Welch, not because they all sound similar but because they all defy comparison. They are unrepeatable in their exquisite sadness.

Although Mitchell lilts softly over the first lines (“When he said…”), complementing the understated acoustic guitar, she does so with absolute surety. She makes her technically difficult descending lines sound totally effortless. The arrangement gains strength of sound for the first chorus (“And I sewed a party dress…”) by adding rich acoustic piano lines, wistful accordion, and subtle hi-hat percussion. Mitchell gains energy for her higher notes and joyfully swoops through many more technically demanding melodies. She can somehow convey the excitement of finding your first love and the visceral grief of losing them at the same time. Then, an accordion solo rips your heart in half.

Although it may be sound over-the-top at this point, she manages to get away with repeating tropes like the plaintive accordion because it feels so genuine. Her loose concept album, Young Man in America (2012), tells simple stories of the complicated bonds between parents and children, with a youthful photo of Mitchell’s father gracing the album cover. She released this album two years after her full-blown rock musical, Hadestown, and critics and fans immediately compared the two records. Hadestown, which recently finished an off-Broadway run, retells the story of Orpheus and Eurydice through the lens of the Great Recession. High-profile guests recorded as the different mythical characters, including Justin Vernon (of Bon Iver) as Orpheus and Ani diFranco as Persephone. On Young Man in America, you can feel her grappling with many of the same issues of economic insecurity while dramatically paring down her production to tell her own story. Both albums are masterpieces in their own right, but the through-line of Mitchell’s voice and truthful storytelling are refreshing on Young Man in America after the beautiful chaos of the 2010 album.

The second verse of “Tailor” continues the tragic love story with the man saying he’s leaving. A low bass piano note underscores the darkness of the scene, before giving way to the mournful accordion and delicate piano floating over the top of Mitchell’s grief (“When he said that my face he’d soon forget, I became a poet.”) After the second chorus, the instrumentation pares down to guitar (“Now that he’s gone away…”), and this sudden absence reflects the gaping hole he leaves in her life. When reaching back to childhood for any trace of her identity, she asks, “Didn’t I gleam in my father’s eye?” And the first line of electric guitar gleams along with her.

It’s fitting that the last vocation Mitchell is called to in “Tailor” is to be “a poet.” She is an incredible poet and storyteller, and ultimately that’s what makes the song so affecting. In the midst of an album about parents and children, Mitchell sings of a kind of romantic love that can push your parents over in your heart a little bit as you grow older. Some of us can probably relate; it’s intoxicating. But what happens when you’ve left your parents’ protection, the new center of your universe leaves, and you’re forced to face yourself as an individual, alone? In her poetry, the sadness of this man leaving her entwines with the sadness of growing up to form a profound loss: the loss of her sense of self. The grace of Mitchell’s composition and poetry make me long to listen to “Tailor,” but I always know it will hurt a little to listen, too.

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Please find below an amazing acoustic concert by Mitchell for NPR’s Tiny Desk series! Note that the version of “Tailor” she plays here is NOT THE SAME as the studio version I reviewed, but it will give you an idea. Or do yourself a favor and buy the album. #boosters