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The Best Breakup Songs Of Our Generation

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There are basically three things that help numb the pain of a breakup: food, intoxicating substances, and songs about losing love. Let’s be honest–of all the genres, pop music has this market cornered. Sure, there are good rock, rap, metal, and country songs about losing the person you love. Hell, I’m pretty sure country songs aren’t about anything other than heartbreak and dirt roads. But like John Cusack said in my favorite movie about love, “What came first, the music or the misery? People worry about kids playing with guns or watching violent videos, that some sort of culture of violence will take them over. Nobody worries about kids listening to thousands, literally thousands of songs about heartbreak, rejection, pain, misery, and loss. Did I listen to pop music because I was miserable? Or was I miserable because I listened to pop music?”

“Fuck It (I Don’t Want You Back)” By Eamon

Get it all out, man. The girl took everything you loved and dropped it into a vat of acid. No, swear all you want–who gives a shit about radio edits? Sure, a lot of breakups are relatively benign, but sometimes you just need to say “fuck you” to the person who ruined your life.

“Since U Been Gone” By Kelly Clarkson

This was tough, because Kelly is the current queen of the breakup song (yes, even better than Adele). I almost went with “Behind These Hazel Eyes” or “Because of You,” but I couldn’t do it in good conscience when “Since U Been Gone” still exists in the world. What’s crazy is that these songs are all on the same album. There hasn’t been a run of songs on this subject on one album that was this good since “Jagged Little Pill.” More on that later.

“She Hates Me” By Puddle Of Mudd

Look, not all breakup songs are doom, gloom, and constant rain. Sometimes you just have to laugh a little bit at yourself, and what better way to do that than through an angry pop-rock anthem about a girl who ripped out your heart and stomped on it?

“Irreplaceable” By Beyoncé

This is on here as a stern reminder that if Jay-Z and Beyoncé ever split, she’s the one who’s going to go off in a song (or possibly a whole album) about it. I love Hova, but the man hasn’t been on top of his game for years, so assuming that he’s going to be able to pull out the fire like he did with Nas is probably a pipe dream. If that divorce happens, expect Beyonce to murder him–lyrically.

“Cry Me A River” By Justin Timberlake

Isn’t it great when someone writes a breakup song and everyone in the world knows who it’s about? There’s no question who won the Britney/JT split. Timberlake wrote one song and completely owned the break.

“Nothing Compares 2 U” By Sinead O’Connor

Sure, it’s the second song on my list that replaces “you” with “u.” No, I’m not particularly in favor of the abbreviation, but you won’t ever hear me speak ill of Sinead. She might be the only person in the world who could take a Prince song about love and catapult it to a level that even Prince couldn’t have accomplished.

“Foolish Games” By Jewel

This is one of my roommates’ go-to karaoke songs. Yes, he’s a man.

“Against All Odds” By Phil Collins

What a fucking brutal song. Living in a room of nothingness with no real reminders of the girl who broke your heart? You just have your own shitty memory of what she looked like. My man Phil Collins gets it. This song is a monument built for the man who’s still at the point where he believes all he can do is wait and hope foolishly that the woman who’s not coming back will somehow walk through the door.

“You Oughta Know” By Alanis Morissette

The angriest breakup song isn’t a rock song or a metal song. It’s a pop song from my lady, Alanis, who spits lines that are more venomous than any rap beef track. I won’t lie–after a particularly unconscious uncoupling, I ran “Jagged Little Pill” over and over in my ears. Do you want to know why, after almost 20 years, people still wonder who this song was written about? Because it perfectly encapsulates the range of emotions you feel when you see your ex with a new boy or girl who clearly doesn’t have what you thought you offered. And you want that person to fucking know it.

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Randall J. Knox

Randall J. Knox (known colloquially to his friends as "Knox") left his native Texas a few years ago, and moved to Los Angeles in his '03 Buick Regal named LeRoi to write movies with his jackass college buddies. His favorite things in life include bourbon that's above his pay grade, mix CDs, and Kevin Costner films. He isn't sure what "dad jeans" are exactly, but he knows he wants a pair.

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