Bitter Pills For Bitter Pills: Five Essential Breakup Songs

In the depths of breakup-induced despair, even a trip to Chuck E. Cheese won't cure what ails you. You need songs that understand. i i

hide captionIn the depths of breakup-induced despair, even a trip to Chuck E. Cheese won't cure what ails you. You need songs that understand.

Courtesy of Chuck E. Cheese
In the depths of breakup-induced despair, even a trip to Chuck E. Cheese won't cure what ails you. You need songs that understand.

In the depths of breakup-induced despair, even a trip to Chuck E. Cheese won't cure what ails you. You need songs that understand.

Courtesy of Chuck E. Cheese

These little five-track playlists can be shockingly difficult to compile: How do you narrow down just five road songs, or love songs, or work songs, or jazz songs? It's so subjective, so fraught with over-thinking, so in need of painstaking research, archive-mining, and what the kids these days call "crowd-sourcing."

Picking five relatively new and utterly devastating breakup songs, however, involved opening my iTunes and sorting by play count. It was tempting to merely string together the Top 5 and call it a day: Bon Iver's "Skinny Love," 101 plays, check; Laura Gibson's "This Is Not the End," 100 plays, check; and so on. Instead, I did about three minutes of curation, decided Cee Lo Green's "F— You" was too obvious, and then called it a day.

So here they are, just in time for the clown-show of the heart that is Valentine's Day: five bitter pills to swallow as you pick through the charred ruins of your life, deface your cherished mementos, and use the absorbent exterior of a Chipotle burrito to soak up your tears.

This is, of course, but a tiny sampling of the bleak breakup music at your disposal: For heaven's sake, not one of these songs even predates 2006. So please, do your fellow heartsick haters a solid and recommend more essential breakup music — Noah and the Whale's The First Days of Spring! Blood on the Tracks! Practically everything by The Mendoza Line! — in the comments section below.

The Five Stages Of Breakup Music

Laura Gibson CD

DENIAL: Laura Gibson, "This Is Not The End"

  • Album: If You Come to Greet Me

Nothing says "I have not yet begun to move on" quite like marinating in Laura Gibson's gently weary voice as she sings, "Forget about the end / Forget about what might have been." Ironic, no? It's remarkable, the balancing act at work here: If you dwell on Gibson's alternately oblique and direct words, hearing "This Is Not the End" is like getting rabbit-punched in the kidneys of your soul, even as the dreamy arrangement dishes out a soothing shoulder-rub. The song won't alleviate what ails you, but you're in denial anyway. That's not what it's there for.

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  • "This Is Not the End"
  • Album: If You Come to Greet Me
  • Artist: Laura Gibson
  • Label: Hush
  • Released: 2006
 
Dolorean CD

PETTINESS: Dolorean, "Country Clutter"

  • Album: The Unfazed

Oh, if only you had the energy for anger — to tilt your head back and let the invective fly as, say, The Mountain Goats' John Darnielle yells, "I hope you die / I hope we both die." But that sort of white-knuckle indignation requires energy, and you can barely muster the strength to pry open your eyelids. Instead, try Dolorean's sweetly slow-burning ode to inconveniencing an ex-lover: "I've moved along, packed up my s— / If there's anything I left behind, well, you can have it," Al James sings. "Let it clutter up your life / the way you cluttered up mine." Hoping someone trips over your old junk may not be as satisfyingly blunt as "I hope you die," but it's a much healthier (and, thankfully, more realistic) brand of pettiness.

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  • "Country Clutter"
  • Album: The Unfazed
  • Artist: Dolorean
  • Label: Partisan
  • Released: 2011
 
Sarah Siskind CD

SELF-PITY: Sarah Siskind, "Lovin's For Fools"

  • Album: Studio/Living Room

When experiencing the five stages of grief, they rarely come one at a time — they overlap and interlock like nobody's business. It's no surprise, then, that one of the world's most heartbreakingly self-pitying songs would also carry with it a glimmer of denial and pettiness: "Go on and love her, love her forever / I will not tell her that you told me, too," Sarah Siskind sings, as if alluding to the fine print in a binding contract. A country-pop weeper that truly belongs in the breakup-song canon — couldn't you imagine some aspiring American Idol contestant just nailing this song on country night? — "Lovin's for Fools" is the most elegant and gorgeous possible way to say, "It's just not fair!"

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  • "Lovin's for Fools"
  • Album: Studio/Living Room
  • Artist: Sarah Siskind
  • Label: Infrasound Collective
  • Released: 2008
 
The Avett Brothers CD

FATALISTIC SELF-PITY: The Avett Brothers, "Tear Down The House"

  • Album: Gleam II

There's "Aw, why did you have to leave?" and then there's wanting to bulldoze everything that has ever mattered to you because it'll never be the same anyway. In the last few years, The Avett Brothers' frenetic live shows have helped the band score a major commercial breakthrough, but its secret specialty is ballads that couch real wisdom in their weepiness. "Tear Down the House" may be The Avett Brothers' best song: a morbid, heartsick wallow that tells real truths about how it feels to plumb the depths of despair. When Seth Avett sings, "I have no memory of who I once was, and I don't remember your name," the saddest part of all is that it's wishful thinking.

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  • "Tear Down the House"
  • Album: Gleam II
  • Artist: The Avett Brothers
  • Label: Ramseur
  • Released: 2008
 
Elizabeth and the Catapult CD

BITTERNESS MASQUERADING AS ACCEPTANCE: Elizabeth and the Catapult, "Thank You For Nothing"

  • Album: The Other Side of Zero

Countless emotions disguise themselves as love: lust, fear, jealousy, aspiration. Similarly, "acceptance" is often the mask worn by an overwhelming desire to have achieved acceptance. Elizabeth and the Catapult's sad, remarkably beautiful ballad may sound at first like a feat of weaponized maturity — singer Elizabeth Ziman knows she should be grateful for a dead relationship's highs, lows and associated lessons — but there's no mistaking the telltale signs of scars that haven't smoothed over. "Thank you for loving me / Thank you for leaving," Ziman sings, adding, "Thank you for promising / and then promptly forgetting." On the surface, "Thank You for Nothing" is just a beautifully ornamented ode to taking the bad with the good. But the emotions involved are more complicated than that: Ziman knows that you can graciously wish someone the best while still wanting him or her to stick it sideways.

 

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