Erik Skaarsgard
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Songs to Listen to When You're Heartbroken

We’ve all been there. A breakup, a death, or that crush that doesn’t know you exist. For those tough days when you could be lonely in the middle of a crowd, these are the best songs to listen to when you’re heartbroken.

Don't worry, broken-hearted lady, help is on the way.

We’ve all been there, world collapsing around us as the walls close in on a drunken shell of a body. The best cure for waking up in a pile of empty whiskey bottles and despair, though, is usually a pop song. 

Whether it’s reassurance that everything will be ok or just some camaraderie, something about these songs makes everything seem a little brighter, if only for a few catchy, sappy minutes. When you’re heartbroken, these songs will either help you feel better or will let you wallow in the pain for a little while longer.

Nothing Compares 2 U - Sinead O'Connor

It’s entirely possible that no song is more recognized for its heartbreak than Sinead O’Connor’s 1990 smash hit. The song perfectly sums up the struggle of the newly single, meshing the triumphant independence with the desperate longing of a lonely husk of a person. 

Originally written and recorded by Prince for a side project in the mid-80s, O’Connor captures the melancholic state of regret better than anyone could ever hope for. 

Somebody That I Used To Know - Gotye (Feat. Kimbra)

The opening lines for this cry for help were ubiquitous on the airwaves for about a year in 2011. You can picture someone screaming the eerie chorus outside a window late at night, “You didn’t have to cuuuuut me off…” 

What better for a good bout of self-loathing than Kimbra’s vitriolic answer “now and then I think of all the times you screwed me over…” Almost certainly the anthem for countless teenage sob stories, the fatalism, and hopelessness of the track translated to a big hit that still gets airplay. Fortunately, when you’re heartbroken, you’re almost guaranteed to find this playing on any adult contemporary radio station. 

Fucked Me Right Up - Sean Hayes

This was never a hit, but when it played at the end of the first episode of HBO’s cult hit Bored To Death there wasn’t a dry eye in the house, or an unsympathetic one. Cohen-esque in its universality, Hayes captures the numbness of heartbreak in an enthusiastically melancholic hymn. 

The song’s simplicity captures staring into space, in disbelief of what’s occurred, but offers just enough hope to keep going. The determination and finality are undercut by doubt, in a cacophony of the emotion’s experienced along with the sudden absence of a loved one. It’s powerful stuff, medicine for the most painful loss. 

So Lonesome I Could Cry - Hank Williams

It wouldn’t be a list about heartbreak without a couple of classic country songs, so why not start with the most classic of all. Really, any number of Hank Williams’ classics could be on this list, “Tear in My Beer,” “Your Cheatin’ Heart,” “Lovesick Blues,” they all belong on a tear soaked playlist.

Something about his lonesome wail in “I’m So Lonesome I Could Cry” puts it above the rest, though. When you’re heartbroken, this song reminds you that heartbreak doesn’t change, everything is a trigger, and there’s no joy in the world. At least for a little while…

Hello - Adele

For that heartbreak that seems to keep coming back like a cancer in remission, look no further than the most iconic voice of modern music. When it comes to songs to listen to when you’re heartbroken, Adele, like many great artists, could put together a greatest hits of lovesick songs by herself. 

But none of her mega hits capture the lingering sting of loss like "Hello." The conversation that makes up the lyrics, whether imagined or real, perfectly encompasses the longstanding regret of a painful breakup (or even a death.) Years later, like the recurring emptiness, the song will be there for comfort. 

We Are Never Ever Getting Back Together - Taylor Swift

It wouldn’t be heartbreak without some ups and downs. For a little celebratory high, you can’t do better than Taylor Swift. It’s only healthy to let that anger out as exuberance and reinforce a positive vibe in your life, so shout it out in the catchiest way possible. 

This will get you through those moments of grief when you’re determined to get through it, no matter how much lying to yourself it takes. She lays out a common scenario of a drama king who doesn’t know what he want’s, so if you’re looking for someone to relate to, Taylor’s there to help you out. Just don’t ask her to get back together, ever.

Skinny Love - Bon Iver

We’ve all been 15 and lonely. That first heartbreak was probably the worst, literally and hyperbolically. Fortunately, you can relive that heartbreak any time you like with a little help from indie darling Bon Iver. The sparse sound screams (or whispers) isolation and the lo-fi leaning production is the perfect sleeve on which to display one’s heart. 

His wavering voice is the icing on the cake, whispering in your ear “you’re not alone, but if you want to be that’s ok…” For heartbreaker bonus points, visit the Bon Iver fan fiction Tumblr to pine over skinny bearded hipsters you’ll never have. This is easily one of the best songs to listen to when you’re heartbroken. 

The Grand Tour - George Jones

George Jones, like Hank Williams before him, is well known and highly regarded for songs that relish the heartbreak and loneliness country music made famous. This song particularly relishes in the regrets of a nostalgia-prone man. 

As the title suggests, the man laments the loss of his wife as he picks through the items in his home and spins yarns about the good times of old. Like many others on the list, Jones is a venerable heartbreak expert, but "The Grand Tour" and its stark imagery really hits hard. 

Answering Machine - The Replacements

The Replacements are an iconic band. Their sound defined college rock from the 80s into the 90s, and their catchy classics are often unabashedly fan-boyish ("Alex Chilton") or downright goofy ("Gary’s Got A Boner.") In between those immature anthems, though, they could be absolutely heartbreaking. 

"Answering Machine," from the classic Let It Be album, has their hearts on their sleeves. Songwriter Paul Westerberg sings of the isolation brought on by leaving messages on an answering machine, the doomed relationship looming in the background. It’s more sparse than most of their songs and could be taken as an afterthought were it not for the beautiful sincerity in Westerberg’s voice. Answering machines may be a thing of the past, but heartbreak and desperation are forever. 

Love Will Tear Us Apart - Joy Division

Joy Division didn’t become the bastions of underground music when they were active. Since their demise, however, singer Ian Curtis and the band that would become New Order have been touted as essential in the canon of indie rock and its related genres. Curtis’ brooding baritone is the primary reason. 

On their most popular single, Curtis laments a relationship gone bad. It’s the perfect song for when the person you love is just out of reach or seems to be floating away in a nightmare cloud. The isolation of Joy Division’s sudden rise proved too much for the singer, and true to his mournful song he hung himself as the band's popularity continued to grow. There’s so much packed into this short anthem it’s bound to be on your list of songs to listen to when you’re heartbroken. 

No Children - The Mountain Goats

The Mountain Goats, led by John Darnielle, are known for wearing their hearts on their sleeves. Darnielle has been releasing music under the name for over twenty years and has come to define a deceptively naive style that doesn’t skimp on the heartbreak. 

If you heard this song playing in the background of a coffee shop you wouldn’t bat an eye, but listen closely, and you’ll discover a dark, vengeful song. With lyrics like “I hope you die/ I hope we both die” and “I hope it stays dark forever… I hope I never get sober” Darnielle isn’t pulling any punches. If you’ve ever needed cheering up while you bask and revel in your loneliness, this one's for you. 

Landslide - Fleetwood Mac

If you’re a fan of South Park, you’ll remember the time Stan’s parents separated. You’ll also know that this is not generally a show to move it’s viewers to tears, at least not sad tears. That made the pain even worse as Randy Marsh packed up his things after Sharon threw him out. But it wasn’t the fact that two beloved characters were separating; it was the fact that "Landslide" was playing over the scene. 

It doesn’t even matter if you listen to this song when you’re heartbroken, even if you’re feeling great you’ll be balling your eyes out after one spin. In fact, you’d have to be a heartless monster not to feel sad when listening to this moving-on anthem. A heartless monster like your ex. 

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