Sad Songs That Hurt Just Right

Sad songs that hurt just right on black background

Sometimes you need a sad song you can play really loud.

Dolly gets you and you’re gonna be okay. Sarah Smarsh suggests a playlist.

When we were making our list of experts on Dolly Parton, we knew we needed to talk to Sarah Smarsh. She’s the author of the New York Times bestseller Heartland: A Memoir of Working Hard and Being Broke in the Richest Country on Earth, and of She Come By It Natural: Dolly Parton and the Women Who Lived Her Songs. And if you listened to Radiolab’s smash hit series “Dolly Parton’s America, you heard Sarah Smarsh.

When Sarah was just a kid riding in her Grandma Betty’s car, she listened to Betty sing along with Dolly’s songs on cassette. Sarah’s grandma was like many of the women Dolly wrote about—she lived a life of hard stories that Dolly told with respect, heart and, of course, a voice and sound so big you could practically lean on it. So when Grandma Betty needed good music turned up loud, she chose Dolly.

“During my 1980s childhood, Dolly was a middle-aged sex symbol known for her outlandish appearance,” Sarah wrote to Whalebone. “Patriarchal culture thus turned her into a boob joke. My grandmother, who had listened to Dolly since Dolly was a feisty young country singer in the 1960s, only saw her as a brilliant storyteller with a beautiful voice and abiding affection for her poor, rural origins. ‘Common as an old boot,’ my grandma would say about such people, which is her highest compliment.”

As Sarah grew up and became a writer and journalist, she kept thinking about Dolly Parton and the ways her songs told the stories of so many of the women she grew up with. Whether you grew up in the heartland or not, Dolly’s songs ring true. Heart crushed by disappointment? Dolly’s got you. Someone stealing your true love away? Dolly knows. And listening to her can make you feel better.

Here’s a playlist for you, curated and annotated by Sarah Smarsh herself, with a nod to Grandma Betty…


Best song for a broken heart:

Two Doors Down

Parton wrote this in the late 1970s, and you can hear second-wave feminism in the sexual-liberation lyrics. She’s been through a breakup, but she’s going to stop crying, go to a party, and get some.

Best song for when you’re mad as hell:

Dumb Blonde

Parton didn’t write her first big hit, but it would foretell an entire career of being underestimated as just a pretty blonde lady.

Best song for when you’re lonely:

The Bargain Store

This is a plea for love, but it’s also a masterful take on the intersection of gender and class. My favorite Dolly song of all time.

Best song for a solo late-night drive:

He’s Alive

An over-the-top Christian pop song telling the story of the Resurrection in the voice of the apostle Peter. But hear me out. Reportedly, Parton heard it on the radio and wanted to cover it. Consider the quiet, feminist audacity of singing this song as a woman. Mary Magdalene told the other apostles that Jesus was alive, and they didn’t believe her—a Biblical point referenced in the song. Parton singing “He’s alive” over and over in the triumphant chorus is not just a testament to her Christian faith. It’s a testament to the female voice.

And a bonus track for when you’re feeling better:

Rockin’ Years

The best song for solid love with Ricky Van Shelton. This 1991 duet, written by Parton’s little brother Floyd, is a classic country song with steel guitar, fiddle and a lilting melody. It was in heavy radio rotation when I was a tween beginning to imagine romance. The video from 30 years ago has 13.5 million views on YouTube and thousands of comments about how this duet touched people’s lives as a wedding dance or a late family member’s favorite song or an exaltation of long-term commitment. Parton herself has been married to the same man since 1966.