The Best Songs for the Worst Literary Breakups

Breakups can be the pit stains on the t-shirt of life, this we know. But for each heartache and heartbreak, there’s always solace to be found in a song that captures exactly how it feels to be kicked in the emotions. It’s the song that you play on repeat, belt out at karaoke after too many drinks, and feel each individual lyric like it was the truest thing ever said about love. So whether it’s your first (thank you, Usher) or your latest (thank you, Gotye), a cathartic break-up song now and again does wonders for the bruised of heart.

So we had to wonder…what are the perfect break-up songs for some of the more iconic romantic tragedies in literature? What should Heathcliff listen to as he weeps into his half-gallon of Breyer’s Heath Bar Ice Cream? (Because really, what other ice cream flavor would Heathcliff buy?)

Catherine Earnshaw & Heathcliff – “Bad Romance” by Lady Gaga

What can we say, the brooding orphan man knows how to hold a grudge. It takes serious dedication to exact a revenge as thorough as Heathcliff’s. And we think Lady Gaga’s “Bad Romance,” with its themes of obsession and the dark side of love, is the perfect anthem to Catherine and Heathcliff’s tumultuous lifelong affair. You can almost hear Heathcliff sing-shouting, “I don’t want to be frieeeeeeeeends!” across the foggy moors.     

Lyric That Nailed It

I want your love and
I want your revenge
I want your love
I don’t wanna be friends

Jay Gatsby & Daisy Buchanan – “F**k You” by Cee-Lo Green

Jay really could have used a dose of this song’s perspective when it came to trying to impress Daisy. Rather than spending all that money on parties and all that time staring at green lights, Jay could have just seen Tom and Daisy driving by and thought, “f**k that, old sport.”

Lyric That Nailed It

Now I know, that I had to borrow,
Beg and steal and lie and cheat.
Trying to keep ya, trying to please ya.
'Cause being in love with your a** ain't cheap.

Anna Karenina & Alexei Vronsky – “I Knew You Were Trouble” by Taylor Swift

Man, Anna Karenina could not get a break in Tolstoy’s (nearly) 350,000-word tome. But what can you expect when falling for someone who is totally flirting with someone else when you meet him? With “Trouble,” Taylor Swift knows a thing or two about falling in love when it’s clearly a bad idea. Plus, the line, “lying on the cold hard ground,” takes on a much more sinister meaning in Anna Karenina’s context.  

Lyric That Nailed It

I knew you were trouble when you walked in
So shame on me now
Flew me to places I’d never been
Now I’m lying on the cold hard ground

Eponine Thenardier & Marius Pontmercy – “Dancing on My Own” by Robyn

I think we can all agree that Robyn’s “Dancing On My Own” is the modern version of quintessential unrequited love ballad, “On My Own,” from the musical Les Miserables. Not only do they share similar titles, but both songs sum up what it feels like to be friend-zoned and overlooked. Girl, we’ve been there, we feel you.

Lyric That Nailed It

I’m in the corner, watching you kiss her
I’m giving it my all, but I’m not the girl you’re taking home
I keep dancing on my own

Lancelot & Guinevere – “9 Crimes” by Damien Rice

Forbidden love at its most medieval—not only do Lancelot and Guinevere betray their spouses, but in some interpretations of Arthurian legend, they kick off the downfall of Camelot. The heart-wrenching “9 Crimes” is well-suited for this guilt-laden duo. The haunting vocals by Damien Rice and Lisa Hannigan, plus lots of slow piano and cello, makes for….WHY IS IT SUDDENLY RAINING ON MY FACE?

Lyric That Nailed It

Leave me out with the waste
This is not what I do
It’s the wrong kind of place
To be thinking of you
It’s the wrong time
For somebody new
It’s a small crime
And I’ve got no excuse

Medea & Jason – “You Oughta Know” by Alanis Morissette

Nobody does jilted, vengeful wife quite like Euripedes’ Medea. You can feel the fury and pain boil off her as she plots against former husband Jason, complete with cannibalism and poisoned diadems! And seeing as nobody has done a better “bitter ex” song since Alanis' “You Oughta Know,” we think Medea must have been vibing off that acrimonious energy.   

Lyric That Nailed It 

'Cause the joke that you laid in the bed
That was me, and I’m not going to fade as soon
As you close your eyes, and you know it
And every time I scratch my nails
Down someone else’s back, I hope you feel it
Well, can you feel it?!

FULL PLAYLIST HERE: