3 of Dolly Parton’s Most Heartbreaking Songs

With a seemingly endless reserve of kindness, Dolly Parton brought joy to so many. But she emerged from poverty, and her path to stardom wasn’t easy. Though she dreamed of a life beyond the Smoky Mountains and her Sevier County home, her rural roots were ever-present.

For this list of heartbreakers, I’ll begin with an obvious choice. But the last two, perhaps, may introduce a couple of gems you might have missed. We already miss her.

“Jolene”

On the set of a 1960s country-music television show, Dolly Parton met a young fan named Jolene. The 8-year-old girl inspired the title character. But it was a flirty bank teller who gave the tune its desperation. Parton noticed her husband Carl Dean was spending more time at the bank, only to learn he was receiving extra attention from a smitten clerk. It became a joke between the couple, but Parton transformed the joke into the eternally anguishing classic.

He talks about you in his sleep,
And there’s nothing I can do to keep,
From crying when he calls your name, Jolene.

“Little Sparrow”

Following the death of her father, Parton recorded a raw bluegrass album that lands somewhere between her down-to-earth roots and cosmic hymns. The title track to the 2001 album features a weeping fiddle, Appalachian folk, and a timeless harmony by Alison Krauss. But when Parton is left singing a cappella—her giant voice, like a sparrow’s wings, pushes against the gravity of heartbreak, fragility, loss. This is soaring past the darkness in search of the light. For many, Parton was that North Star.

All ye maidens, heed my warning,
Never trust the hearts of men.
They will crush you like a sparrow,
Leaving you to never mend.

“Down From Dover”

“And time is running out for me / I wish that he would hurry down from Dover,” Parton sings about a pregnant teen who’s hoping the father will return. While she waits, she’s rejected by her family. Her baby dies at birth, and the girl sees the death as a sign that her lover won’t be returning. One of Parton’s saddest songs, her quivering voice distills naivety, abandonment, and shattering loneliness.

The sun behind a cloud just cast a crawling shadow,
Over the fields of clover.
And time is running out for me,
I wish that he would hurry down from Dover.

Photo by Shirlaine Forrest/WireImage