Blissful Songs for Your Broken Heart

Blissful Break Up
Alas, the good tidings and romantic spirit of St. Valentine’s day are no longer succulent in the air. Love grew and bloomed, then froze and died. “No!” cry the dreamers. “Say it isn’t so.” It’s so. We started the week with Indie Love Songs for Your Hipster Valentine, now it’s time for some songs to speed you through romantic fallout.

Senior Editor Tony Russo and I compiled a list of our favorite torch songs from most every era and genre in the last one hundred years. Most of the songs are available on a Spotify playlist. Songs not included: I Want You (Fiona Apple Version), Against All Odds—The Postal Service.

Bye Bye, Love — Ray Charles

Ray Charles’s “Bye Bye, Love” is the quintessential song pain of unrequited love. The lover leaves the beloved and his world comes crashing down. “Bye bye, love/ bye bye happiness/ hello loneliness/ I think I’m gonna cry.”

I Am Trying To Break Your Heart — Wilco

Doubt, confusion, self-perpetuating pain mechanism… it’s a Wilco song of heartbreak. Each verse closes with a “What was I thinking when…” statement. It’s as if Jeff Tweedy is reflecting on the conditions of love and they’re less than favorable.

Crown of Love — The Arcade Fire

Assumptions of love and mind crushing insecurity go hand in hand. “If you still want me/ please forgive me/ the crown of love/ is falling from me.” It’s indifference in the face of affection.

Skinny Love — Bon Iver

Skinny, unsubstantial love holds this piece together. “And I told you to be patient/ And I told you to be fine/ And I told you to be balanced/ And I told you to be kind. In the morning I’ll be with you/ But it will be a different kind/ I’ll be holding all the tickets/ And you’ll be owning all the fines.”

One Less Bell to Answer — Fifth Dimension

“One Less Bell to Answer” was written by Burt Bacharach and Hal David to express extreme lamentation over lost love. Marilyn McCoo absolutely owns the vocals on this piece. The outfits in the video are also noteworthy.

I Didn’t Understand — Elliott Smith

This is the emotional bottom of our playlist, when all the sadness is turned inwards. “You painted pictures of a never never land/ And I could have gone to that place/ But I didn’t understand.”

I Want You — Fiona Apple, Elvis Costello

“I Want You” starts off innocently enough but quickly turns devilish. Elvis Costello’s lyrics inhabit a fanatical stalkers mindset. Fiona Apple’s facial expressions say it all.

Against All Odds — The Postal Service

Phil Collins sentiments blend with Ben Gibbard style creating a melange of synth-pop sadness. This is the essential torch song. The singer has been left by his lover and hopes, just for a moment, she will look back at him and realize how much he loves her. But let’s be real. It’s the most pathetic situation a person can be in and Collins screams his bloody heart out. It’s a golden gem of The Postal Service’s lesser-known catalogue.

It Is Not Meant To Be — Tame Impala

As with all things, time sinks in. Guy is mesmerized by girl. She doesn’t much care for him. Things fall apart.

Your Ex-Lover Is Dead — Stars

Time heals all things. A former couple is introduced after time apart one struggles to remember the other’s name. See? Life will be simple in a little while.

Spit On A Stranger — Pavement

Relationships are cyclical. Disillusionment comes, but there are plenty of other people to get caught up in. Detachment followed by quick reattachment are valuable skills.

Selfless, Cold, And Composed — Ben Folds Five

It’s still the cool, dark aftermath of the breakup. The singer is upset at how differently each member is taking the break up. He got worked up, she seemed not to care at all. Note: this video is young Ben Folds Five at its best.

How It Ends — DeVotchKa

Almost religious in nature, “How It Ends” gives a lesson on inevitability. Memento mori.

If You Ever Need a Stranger (To Sing at Your Wedding) — Jens Lekman

Heavily discounted as over-the-top, Jens Lekman really hits a melancholic chord with this one. A lonely singer offers to sing odes and praises of love and weddings, just so he can witness true love. He knows all the songs, but they aren’t yet for him.

Roses — Outkast

People might hold love above all things, but in the end roses don’t smell all that great. It’s a west side story music video.

Breaking My Heart — Aqualung

The more some love, the more they hate. Despite our greatest intentions, we are drawn to painful love.

Somebody That I Used To Know — Elliott Smith

“I had tender feelings that you made hard/ But it’s your heart, not mine, that’s scarred/ So when I go home I’ll be happy to go/ You’re just somebody that I used to know.”

I Can’t Make You Love Me / Nick of Time — Bon Iver

A Bonnie Raitt original in Justin Vernon style.

It Ain’t Me, Babe — Johnny Cash & June Carter

Everybody has the perfect someone to dote on all their needs. It’s just not Johnny Cash or June Carter. Better than the Bob Dylan original.

Walking Away — Brother Ali

Some people have infectious charms, but they are hardly ever worth it in the end. Breaking up is right for some.

One Angry Dwarf And 200 Solemn Faces — Ben Folds Five

More Ben Folds Five power-piano. The trio goes wild with exuberance casting aside all rejection in the past. Ben Folds’s lyrics suggests an it’s-their-loss-anyway attitude. “If you really want to see me, check the papers and the TV/ look who’s telling who what to do. Kiss my ass/ goodbye.”

The Walk — Mayer Hawthorne

Mayer Hawthorne brings R&B to a modern story with biting hate. He only stayed with her for her great looks anyways. The music video involves lots of guns. Lots of guns.

Breakin’ Up — Rilo Kiley

Rilo Kiley sums it up perfectly. A relationship might have been good but “Ooooo, it’s good to be free.” An independent group made the music video and it’s phenomenal. The guys dance moves bring down the house.

As per usual, if there are any heart-wrenching break up songs we missed, put them in the comments section.

  • Jon Catlin

    I do appreciate the last video. Very much so.

    • Tony Russo

      @Jon Catlin Flip phone sighting!

  • Blake J. Graham

    I considered adding this song to the list. If you take Whitney Houston’s “I Wanna Dance With Somebody” and slow it down to really drap out the lyrics, you get this gem:

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