Every Monday in Listening Closer, Jeffrey Overstreet opens up the art of songcraft, sharing his own musical experiences, interpretations, and epiphanies, while soliciting alternate interpretations and discussion.

Last week, I invited you to listen closer to Björk’s song “Stonemilker,” the first song on Vulnicura, the Icelandic artist’s brave and beautiful musical chronicle of struggles with (and, ultimately, severance from) a great love. As I marinated in that music, I began thinking about how commonly I hear songs about heartbreak, but how rarely they have that raw, serrated quality of actual human experience.

I continue to find tremendous value in attending to art that expresses such suffering. To vicariously experience another’s feelings of betrayal, loss, and grief can increase our appreciation of true love; caution us about our capacity for hurting one another; and cultivate empathy for others.And then I posted a question on Facebook and elsewhere: What breakup songs or breakup records mean the most to you? What music do you find entangled in your own hurtful experiences of separation?

The floodgates burst open.

Music critic Andy Whitman pointed to several breakup albums: Bruce Cockburn’s Humans, Van Morrison’s Hard Nose the Highway, Jackson Browne’s Late for the Sky, “and a new one I just heard this week, St. Lenox’s Ten Songs About Memory and Hope.” (Here’s “Just Friends.”)

Singer/songwriter Jessica Smucker pointed to Sinéad O’Connor’s cover of a Prince song: “I’ve still got a soft spot for ‘Nothing Compares 2 U.’” (Listen to her own song “When It’s Time to Move On.”)

Denise Frame Harlan, a writer and English teacher, said, “Best breakup song line goes to T Bone Burnett for ‘I’ve been getting over you / since the day we met’” (from The True False Identity).

Novelist Kate Bassett wrote in with For Emma, Forever Ago, by Bon Iver; Charlene Soraia’s version of “Wherever You Will Go”; the Mountain Goats album Get Lonely; Beck’s Sea Change; “Gale Song”—the Lumineers; Amy Winehouse’s “Back to Black”; “Suitcase”—Over the Rhine. She added, “Clearly, I like breakup music. (still happily married!!)”

Animator Ken Priebe posted this: “Does shooting your lover to death count as breaking up? If it does, then ‘Delia’s Gone’ by Johnny Cash.”

I’d say that counts.

Some choices surprised me: The Waterboys’ “Rags.” The Beatles’ Let It Be (“the break-up album that broke up the band”). Kristen Glass was just one of those who highlighted one of my all-time favorites: the almost-but-not-quite breakup album Drunkard’s Prayer, by Over the Rhine. Rick Bennett picked Weird Al Yankovic’s “One More Minute”:

Then I took your name out of my rolodex,
And I tore all your pictures in two,
And I burned down the malt shop where we used to go
Just because it reminds me of you…

And there were others that seemed almost obligatory: The Cure’s Disintegration (especially “Pictures of You”). “Liz Phair’s entire catalog.” More than one mentioned William Fitzsimmons’ The Sparrow and The Crow. Achtung Baby was forged while one of U2’s marriages crumbled, and so we have “One,” “So Cruel,” and “Love is Blindness.” Several people nominated Bob Dylan’s Blood On the Tracks (especially “Tangled Up in Blue”). And, sure enough, Thomas Bona and Brian Newcomb spotlighted that shattering monument to the marriage and divorce of Richard and Linda Thompson: “Shoot Out the Lights.”

You can read and add to the whole list here.

And that brings me to my own most-significant breakup album.

You probably have rituals like my wife and I do. When a favorite artist releases a new album, Anne and I often sit down together, press play, and listen all the way through without speaking. We’re listening closely—to enjoy what is familiar, to share surprises as they come, to let our radar scan for poetic resonance between lyrics and ideas. (I usually take notes, because I think by writing things down.)

On April 27, 2004, we lit candles, poured glasses of wine, aimed the speakers at just the right angle, and listened to Sam Phillips’s new album A Boot and a Shoe. We’ve been listening to Sam for decades, and I could write a book on how her songs have spoken powerfully into my life. Very quickly, I realized what was happening: In a sequence of thirteen songs, Sam was telling us the story of a marriage. And it took me to pieces, song by song.

In “Open the World,” she sings, “You caught me wanting and the shame in my eyes / was so inductive / that it magnetized you / Pulling down my need.” Is this a reflection on what drew the Singer and Her Muse together in the first place?

This leads (in “Infiltration”) to the days when they have nothing left to share:

Making both sides of the conversation
Sometimes, I don’t know what to do.
Don’t start talking inside my head
If you’re a dead man then stick to being dead.

The sharpest lines on the album (in “If I Could Write”) mark the moment of truth:

I took your ring that never comes off
And put it on —
Sorry to lose you,
Sorry to keep you
After you were gone.

My personal history has two major break-up scars from experiences I’ve called “open heart surgery without anesthesia,” and I stand by that description. I wouldn’t wish such an experience on anybody. Thirteen years ago, Sam sang, “Time doesn’t heal / The scars turn into wounds. . . .” And it’s true. While I have been joyfully and gratefully married for seventeen years, I learned while listening to A Boot and a Shoe that a two-decades-old heartbreak can still ache. These songs released emotions that bled like tree sap from old storm-damage.

But it also reminded me that those calamities became seasons of intense prayer, of angry but meaningful arguments with God, of struggles with pride and jealousy. And I see now that those were times of rare intimacy with Christ, for there is no suffering we can experience that he does not understand.

Moreover, I continue to find tremendous value in attending to art that expresses such suffering. To vicariously experience another’s feelings of betrayal, loss, and grief can increase our appreciation of true love; caution us about our capacity for hurting one another; and cultivate empathy for others. It is a way of learning to love our neighbors. It can unite us—fractured creatures, incomplete, vulnerable and needy. We are, all of us, broken up.

In what may indeed be the most beautiful song she’s ever sung—”Reflecting Light“—Sam Phillips illustrates that even in her broken state (perhaps especially in that state) she can open herself to, catch, and share grace.

I rode the pain down,
Got off and looked up,
Looked into your eyes.
The loss opened windows all around,
My dark heart lit up the skies.

Now that I’ve worn out, I’ve worn out the world,
I’m on my knees in fascination
Looking through the night
And the moon’s never seen me before
But I’m reflecting light.


  1. Is it wrong to not be able to relate to breakup songs? I’ve had my share of heartbreak, but it was never so severe that I had to write or listen to a song about it.
    Breakup songs confuse me more than anything(probably why I can’t stand t swift)… I wonder about the story, about the other side that doesn’t get a voice in the song. Many seem to be centered around people making foolish decisions (sometimes knowingly so) on who to love and give their hearts away to (please correct me if I’m wrong).

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