Best Breakup Music

by | October 19, 2010
filed under Can-Con, Feminism, Pop Culture

After a breakup it can be really tempting to listen to sad love songs, and while that’s probably a stage you’ll have to go through, eventually you get to the point where you want to remind yourself of how important it is to look out for yourself. Haven’t been through a breakup like this in a couple years, but the songs are good for all times. What are your favourite songs for putting things in perspective? Add in the comments below!

Old School

1. I Will Survive – Aretha Franklin

No explanation necessary.

2. These Boots are Made for Walking – Nancy Sinatra

…although I can’t quite get over the awful lyric “You keep lyin’ when you oughta be truthin'”, this song is a classic.

3. Hit the Road Jack – Ray Charles

I guess this song could be interpreted as an anti-breakup song but I always choose to side with the women telling him to hit the road.


1. Movin’ On – Po’ Girl

“I think we’ve reached that old movin’ on.”

2. Fuzzy Slippers – Carolyn Mark

The repetition of the line “Somedays it pays to get out of bed” gives it a spot on the list.

3.The Cheapest Key – Kathleen Edwards

“But don’t get me wrong, here comes my softer side…and there it goes/’cause I’ve been on the road too long to sympathize with what you think you’re owed.” FYI the “explicit” in the video title refers to the fact that the word “bullshit” is in the lyrics.

4. All Your Fault – Broken Falls Community Hall Band

Ok, this is shameless self-promotion for my old band. I wrote All Your Fault to commemorate a relationship that had not one, but three breakups.

5. Willow – Sarah Slean

Gotta put yourself in the mindset of a tree for this one.

Country and Alt-Country

1. Everything is Free – Gillian Welch (or Chris Pureka)

“I just stay home. And sing a little love song, my love, to myself. If there’s something you want to hear you can sing it yourself.”

2. The Long Way Around – Dixie Chicks

Journey not destination, etc.

3. Brand New Starts – Erica Wheeler

Erica Wheeler isn’t very well known but she has some lovely alt-country/folk songs, including this really pretty one about coming back from tough times.

Feminist Staples

1. Superhero – Ani DiFranco

I also really like her song “Shroud”, which is about questioning the things you think you need.

2. Closer to Fine – Indigo Girls

3. As Cool as I Am – Dar Williams

“I will not be afraid of women.”

Musical Theatre

1. Shine Like the Sun – from 9 to 5

“I will prove my own worth, heal the damage and hurt that’s been done. When the cryin’s all done, well I’m going to shine like the sun.”

2. Without You – from My Fair Lady (not the one from Rent)

“You, dear friend who talks so well. You can go to Hartford, Hereford, or Hampshire!”

3. It Sucks to be Me – from Avenue Q

“Why are you all so happy?”

“Because our lives suck!”


1. I’m Not Crying – Flight of the Conchords

Sometimes there’s nothing to do but laugh at the situation.

2. Always Look on the Bright Side of Life – Monty Python

It could be worse.


1. You’re So Vain – Carly Simon

You probably think this blog post is about you. Don’t you?

2. Ciao! – Lush

“I never thought that I could feel as great as I do today. ‘Cause you were nothing but a big mistake.”

3. Hate on Me – Jill Scott (or Glee cast)


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