The breakup tracks less taken

Heartbreak sucks, but the soundtrack to your undying pain doesn’t have to

This article was published on 02.14.19

This is an extended version of a story that appears in the February 14, 2019, issue.

After my first serious relationship ended, I spent months obsessively curating a conceptual three-CD playlist about a modern-day civil war that divides a couple and results in a nuclear explosion. It was ridiculous.

Over the years, my personal catalog of breakup music has only expanded, thanks to what my therapist describes as an inability to truly communicate or blah, blah, blah. I wasn’t really listening.

But hey, you know what they say: Unlucky in love, very lucky in self-pitying soundtracks.

These are some of my favorite spurned love songs, which is to say they’ve felt ripped from the open chest cavity where my heart used to be.

I don’t know if they’ll skewer you the same way; I kind of hope they don’t. Because, man, heartbreak sucks, doesn’t it?

“Can’t Satisfy,” The Impressions

Sometimes hindsight can be a cold shiv in the gut. “I found out in time / What was on your mind / You never planned to stay / Didn’t love me anyway.” If you ignore the resentful words, you’d be forgiven for spinning this dose of Motown ecstasy at Christmastime. Curtis Mayfied’s uptempo falsetto flies and the session players keep the pedal down for two-and-a-half toe-tapping minutes. When the goosebumps-inducing sax solo flares, try not to levitate. “Woo!” indeed.

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“Boots of Spanish Leather,” Bob Dylan

This track comes from the nasally bard’s early, acoustic days, meaning it’s so stripped-down and bare you can almost see bone. Sung as a dialogue between two people—one setting sail to new adventures, one not realizing this means goodbye—it’s a gutting reminder that you can feel so close to someone and yet never truly chart their changing heart.

boots of spanish leather from joan baez on Vimeo.

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“I Wish Someone Would Care,” Irma Thomas

Thomas sings like she’s crying her way up to the pearly gates. Feeling sorry for yourself never sounded so enchanting. Caution: May induce swooning.

“The Tracks of My Tears,” Smokey Robinson & The Miracles

Sometimes an R&B oldie you’ve heard a hundred times never means anything until something happens and then OH MY GOD THIS IS ME NOW. This is one of those songs for me.

“I Am Not Willing,” Moby Grape

Singer Don Stevenson’s voice wavers like his resolve in this late ‘60s gem about a guy reflecting on a doomed pattern in a hot-and-cold relationship. You actually hear him get wise to the mercurial object of his affection.

“Age of Consent,” New Order

The surviving members of Joy Division toy with teenage anthem status here. I’d be shocked if this back-beating, bass-licking, vibrating earworm hasn’t soundtracked a roller rink breakup. The lush keyboard cameos feel like warm rain. And the lyrics, while a little oblique, include a killer couplet that nails how circumstances seem to conspire when two people are at their weakest: “Do you find this happens all the time / Crucial point one day comes a crime?” Why yes I do.

“Too Late to Turn Back, Too Early to Say Goodbye,” The Flaming Stars

I haven’t met many who have even heard of this English alt band from the ‘90s, which is unfortunate. Their haunted, bass-and-keyboard-heavy sound brings the garage into the pub. The title to this one pretty much says it all. Good for that one last slow dance before you never see each other again.

“What Difference Does It Make?” The Smiths

His Supreme Lord of Wallowing, Morrissey, is in fine, acidic form here with this angular adieu.

“You Threw a Spark,” Crooked Fingers

This trumpet-blowing take-down excavates all your partner’s insecurities and weaponizes them in savage fashion. Listen to this when you don’t just want to burn the bridge, you want to napalm the one who helped you build it, too.

<div class="mb-extra"> <iframe style="border: 0; width: 100%; height: 120px;" src="https://bandcamp.com/EmbeddedPlayer/album=1402121998/size=large/bgcol=ffffff/linkcol=de270f/tracklist=false/artwork=small/track=1233594115/transparent=true/" seamless>Red Devil Dawn by Crooked Fingers</iframe> </div>

“Brother, My Cup Is Empty,” Nick Cave & The Bad Seeds

Calling this a breakup song is a stretch even for me, but there is an ambiguous (and incredibly dark) reference to a bad relationship. Besides, this frenetic, pulsing rocker provides the cathartic outlet you need when you’re feeling self-destructive.

“Anemone,” The Brian Jonestown Massacre

Thanks to the gentle-jangling guitars, dazed percussion and Mara Keagle’s hot-breath vocals, this one feels like the painkillers are finally kicking in.

“I’m Straight,” The Modern Lovers

The most unaffected track on this list, it’s also Jonathan Richman at his slacker-sounding peak with his short-lived band. For the straight-edge crowd who doesn’t know why they keep losing out to drugstore loser types like Hippie Johnny.

“These Days,” Nico

The German multi-hyphenate with the thick banshee brogue sends us a postcard from her self-imposed exile. Spending her days shunning human contact, she doesn’t have it in her to try anything again, much less love. “I had a lover / I don’t think I’ll risk another these days.” Turns out there are worse things than heartbreak. There’s the numbing emptiness that swallows it.

“But It’s Alright,” J.J. Jackson

The belting soul singer dusts off his shoulder to a stutter-stepping melody. The result is so catchy you may even start to believe it actually is alright.

“It Just Dawned On Me,” John Doe & The Sadies

Legendary X frontman John Doe fronts this finger-picking country kiss-off with a twist. When people ask, “Do you like country music?” I’m like, “Good country music,” and they’re like, “Well, what does that mean?” and I’m like, “THIS.”

“Don’t Forget Me,” Neko Case

Somehow finding the overlap in wry fatalism and genuine pathos with lines like, “I’ll miss you when I’m lonely. I’ll miss the alimony, too,” Case’s tumbling piano ballad to the ex she still warmly regards is that realistic love song—the kind that reminds us life is long and sometimes two people just run out of road.

“Pale Blue Eyes,” The Velvet Underground

One of the most beguiling breakup songs from this country’s finest rock and roll band. Lou Reed’s cryptic short story covers two people who are so in love and yet so imperfect for each other, and seems to time jump to an illicit affair, when one of them is married. Sterling Morrison’s honey-dripping guitar licks make the infidelity go down like aged bourbon.

“Something for You,” Sarabeth Tucek

By the time this elegiac lullaby winds down, Tucek is ready to move on but cracking a door: “I’ve gone and left this song, but I leave the ending up to you.” I can’t think of a better note to end on than with a glimmer that it might still work out.

The breakup tracks less taken

Heartbreak sucks, but the soundtrack to your undying pain doesn’t have to

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