You Oughta Know… these breakup songs.

If you’re a reader or Twitter follower or friend of mine, you know about my absurd vendetta against Taylor Swift. Talking about her really makes my blood boil, and I left my dad in a fit of laughter a few weeks ago when a repeat of her interview on 60 Minutes kicked off a soliloquy about all of the opinions I have about her. I have a lot of opinions.

So this week, when Taylor struck again with a post-breakup tweet, I tried to ignore it. Then I started chatting with Shannon about it, and she wrote Taylor’s new song in about 30 seconds:

Shannon:  hahaha
I can’t wait to see her twist Harry into something
I bet it’s called like “my own direction” or something silly like that
me:  LOL
you’re totally right
Shannon:  i could probably write it right now, the lyrics at least, in an hour
Shannon:  I’m moving on, in my own direction. your grip is gone, this is my own song, no looking back, the future is mine, watch my back. as i walk away, in my own direction
BAM! Done

When this song inevitably comes out, we want royalties.

Anyway, then I read this brilliant post on Thought Catalog, which included this thought:

0:37 — So far, as revenge songs go, this is no “Cry Me a River.” I am convinced that “Cry Me a River” is what caused Britney Spears to lose her shit for a decade. Have you seen the live version of that song? It has a FULL GOSPEL CHOIR. If someone released a number one song with a FULL GOSPEL CHOIR about how I was a lying, cheating ho-bag who cried fake tears, I’d lose my shit too. Just like Britney did.

It’s true. Cry Me a River is one of the best breakup songs ever written – the video was brilliant, you knew it was about Britney, and then Justin moved on. And it got me thinking – what are my favorite breakup songs? I’m glad I asked!

These are all songs I have played for myself at some point in time following a breakup, listed in no particular order. It is by no means an inclusive list – there are far too many great breakup songs for that, often by these same artists – but the first ones which came to mind after scouring my iTunes. Bookmark this page for the next time you need a breakup playlist.

Alanis Morissette – You Oughta Know

Remember when you were a teenager and heard this song for the first time? If you were like me, you listened and wondered how is she so angry? I hope I’m never that angry. And then you live, and someday you are that angry, and you dig this song out and play it as loud as you can.

The Airborne Toxic Event – Sometime Around Midnight

Because it hurts like hell the first time you see them with someone else, and sometimes you just don’t know what to do with yourself.

Carrie Underwood – Before He Cheats

My favorite song in the world to sing at karaoke.

No Doubt – Don’t Speak

This song was perfection in 1996. It still is, actually.

Adele – Rumour Has It


Many prefer the more melancholy Someone Like You, but in my opinion, if someone has broken my heart, why would I want to find someone like them again? I prefer this one, the feistier fuck you anthem with the fantastic beat.

Kelly Clarkson – Behind These Hazel Eyes

Kelly is the master of the breakup song in a way that Taylor Swift can only dream to be, and out of her many, this is my favorite, because no matter how badly they hurt us, they should never see us cry.

The Beatles – Yesterday

Because, duh. And because I sang an all-female barbershop quartet arrangement of this song in ninth grade.

Bon Jovi – Always

When he holds you close, he pulls you near / When he says the words you’ve been needin’ to hear / I wish I was him with these words of mine / To say to you till the end of time… Whoever this other guy is, he is not Jon Bon Jovi, so that woman is very, very stupid.

Christina Aguilera – Fighter

Take it from me – if you go through a terrible breakup, and you funnel your energy into working out, make sure this song is on your exercise playlist and you can run for miles.

The Clarks – Better Off Without You

Every yinzer’s official breakup anthem.

Coldplay – The Scientist

Because every breakup anthem playlist needs to include the song that will make you cry. This one is mine.

Dave Matthews Band – Grace is Gone

OK, two songs to make you cry. “One drink to remember then another to forget” is one of my favorite lyrics of all time.

John Mayer – Slow Dancing in a Burning Room

Not quite a breakup song, more of a we need to break up song. “I’ll make the most of all the sadness, you’ll be a bitch because you can. You try to hit me just to hurt me so you leave me feeling dirty because you can’t understand.” Say what you want about John Mayer, this song live is close to musical perfection.

NSync – Bye Bye Bye

Breakup anthem meets bubblegum pop. Don’t pretend you don’t still know the dance moves.

Which ones did I miss?


9 thoughts on “You Oughta Know… these breakup songs.

  1. So very many to choose from! Breathe Again by Sara Bareilles and Happy Ending by MIKA are both great for indulging in the sad part and Keep Breathing by Ingrid Michaelson is a perfect mantra for getting through the shit.

  2. Does “You oughta know” being about Dave Coulier make it better or worse?

    And “Sometime around midnight” is a spectacular song. In my Top 50 of all time.

  3. Great post. I would also like to submit to you “On Saturday” by the Clarks, “Song for the Dumped” by Ben Folds, “Fuck You” by Cee Lo, Cake’s version of “I Will Survive,” and wasn’t there some Alicia Keys song that came out in college?
    Charlie submits “Old Apartment” by BNL and “Used to Love Her” by GNR. The latter one kind of scares me, as in, “I used to love her…but then I had to kill her.”

  4. I’d like to add Mumford & Sonds “Little Lion Man.” This song (and well whole album) pulled me through a dark time. And every time I hear “Little Lion Man” I imagine it’s one big “Fuck You” to my ex as in I hope he thinks about me every time he hears it thinks “I really fucked it up this time.” I kind of think it’s a painful song for him to listen to the whole way through.

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