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10 Best Breakup Songs for Grownups (Even If You’re Not Breaking Up)


As I’ve grown older, music has become less and less important to my daily life. When I was a kid and then a teenager, music was always on. My dad was a huge music fan and introduced me to stuff (as I kicked and screamed because all I really wanted to hear was Michael Jackson and Foreigner and Duran Duran) like Bob Marley, Van Morrison, the Beatles, Tom Waits, and Bob Dylan. I’m forever grateful for that early music education.

As a teenager, I bought a lot of records, tapes, and then (finally) CDs. And when iPods came out, I loved making my own playlists. My musical tastes evolved from 1980s pop (yes, even New Kids on the Block) to 1990s darkness (Smiths, The Cure) to pop again to indie mainstream (Wilco, Feist, Death Cab For Cuties).

Somewhere between graduate school and being a new parent, the music has died in my house, in my head, and in my heart.

Yet during the last weeks I’ve been reading (and reading and reading) stories of friendship loss, submissions for our next anthology about friendship breakups and loss called “My Other Ex: Women on Losing and Leaving Friendship.” Many of the stories are sad, others are incredibly dark and tragic, others are bittersweet, and lots are laced with nostalgia. I’ve also been writing my own story of a friendship breakup, one which is deeply entangled in my memories of the worst romantic breakup of my life.

Part of what my co-editor Stephanie and I have learned quickly about friendship breakups is that women describe them as just as painful and confusing and sad as a romantic breakup. So maybe that’s why I have all these breakup songs in my head. Because these stories of loss are just as mournful as any I could write about any romantic breakup.

You see, back in my twenties and early thirties, I was a serious breakup mix maker. When I was going through breakups — serious ones, painful ones, stupid ones, silly ones, bewildering ones — I developed a ritual to get over every relationship. When I was going through the first hours and days after a relationship ended, I wanted music, only music. Normally there is nothing more soothing and able to bring me pleasure as books or a great television show. But then I wanted poetry set to music. I wanted raw words and emotion. Just for a while. No fillers, just the cut to the bone words of great songwriting.

Here were my standards, my go-to songs for getting through heartbreak, and they are the songs that find myself wanting to listen to as I read these women’s stories.

  • “Everything Reminds Me of Her” by Elliot Smith. Elliot died young, and I can’t listen to his music without thinking about his battles with drug addiction and depression. He was a dark soul but a gifted one.

My favorite line: “I never really had a problem because of leaving/But everything reminds me of her this evening”

If you like this, try: Say Yes by Elliot Smith

  •  “Nothing Compares 2 U” by Sinead O’Connor. This was the first breakup song that I couldn’t stop listening to. The pain and emotion in her voice can still take your breath away, even decades later.

If you like this, try: “When You Were Mine” by Prince/Cyndi Lauper

  • “I Am Trying to Break Your Heart” from Wilco. This song takes a while to get going, but (as usual) it’s brilliantly written and strangely addictive.

Favorite lines: Let’s forget about the tongue-tied lightning/Let’s undress just like cross-eyed strangers/This is not a joke, so please stop smiling/What was I thinking when I said it didn’t hurt?”

If you like this, try: “You and I” by Wilco. Not technically a breakup song, but not exactly romantic in the traditional sense. I lobbied hard for this to be the first dance song at our wedding, but my husband vetoed it because of lines like “Oh, I don’t wanna know/And you don’t need to know/That much about me”

  • “Pictures of You” by The Cure. Every breakup, every time, this song was on repeat.

  • “Most of the Time” by Bob Dylan. In normal times, I’m not a huge Bob Dylan fan. I appreciate his talent and his lyrics, but his voice gets in the way for me. However, during times of breakup, I reached for the Dylan albums. I had a hard time picking between “Most of the Time” and “Don’t Think Twice,” but I think this one wins out because it’s in one of my all-time favorite movies, “High Fidelity” (as well as my favorite Nick Hornby novel, one that I’ve read about 100 times). And that repeated line, “most of the time?” Gets me every time.

If you liked this, definitely try: “Don’t Think Twice, It’s All Right” (which includes some of the greatest lines in breakup song history, like: “I ain’t sayin’ you treated me unkind/You could have done better but I don’t mind/You just kinda wasted my precious time”)

  • “You Oughta Know” by Alanis Morrisette. So is there any song — any song — that so perfectly conveys the rage, anger, hurt, desperation, and temporary feelings of mental instability that accompanies a breakup?

I loved this song when it came out in college and listened to it many times after breakups in my twenties. But sort of half-heartedly, you know? Because until the breakup that I had before I turned 30, no relationship really justified that level of passion and rage. Then I had one that did (the subject of my anthology piece for the next book) and the song basically was played on repeat for more than six months. I remember, in fact, one day when I was visiting my mom and sister a few months after my breakup. My sister and I were shopping in a book store when this song came on. I started to listen to it, stopped to hum it quietly (or so I thought), and in a second all my anger and feelings came right back and apparently I got a little to “into the song” for a public place. The next thing I knew I looked over at my sister and she shook her head out of pity and embarrassment and said, “You really have to stop listening to that song.”

  • And my favorite breakup song (and the tenth breakup song on this list that I recommend) is “A Case of You” by Joni Mitchell. Just listen to it, again and again.

“You’re in my blood like holy wine
You taste so bitter and so sweet

I could drink a case of you darling
And still I’d be on my feet”

Favorite lines: “I met a woman /She had a mouth like yours/ She knew your life /She knew your devils and your deeds/And she said  ‘Go to him, stay with him if you can/But be prepared to bleed'”

All of these songs are about loss, and they could be about the pain from losing a relationship of any sort — friend, lover, spouse.

Do you have a favorite breakup song that got you through a tough breakup, either with a friend or partner? 

If you have gone through a friendship breakup, we’d appreciate it if you’d take our friendship breakup survey. Stay tuned at The HerStories Project to learn more about our next book!

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  1. Mike says:

    Phil Collins has entire albums dedicated to breaking up songs, he should have at least one on here… “I don’t care anymore” is a haunting classic beautiful break up song

  2. This is an awesome list!

    Oh… Nothing Compares 2 U… how that brings back memories of high school break ups. Ha! Pictures of You – absolutely!

    Another one is End of The World (sung by Karen Carpenter):
    “Why does the sun go on shining? Why does the sea rush to shore? Don’t they know it’s the end of the world… ‘Cause you don’t love me anymore?”

    Thanks for sharing. Wishing you a lovely day.
    Jennifer | The Deliberate Mom recently posted…The Tale Of Two BagelsMy Profile

  3. Jessica, this is such a great list. I especially love Wilco and The Cure. I feel like I’m in high school, sitting on the floor in front of my huge stereo, trying to figure out the perfect order for my next mixed tape. Ah memories.
    Also, I’m so sorry that I didn’t contribute anything to the next Her Stories book. I kept writing it in my head but it just never really came to fruition. I’ve no doubt that the next book will be amazing.

  4. So interesting, Jessica! I, like you, have lost touch with my musical past. I wonder if this happens to people as they get older? I don’t know. As for break-up music, there are some songs I just cannot listen to anymore because they remind me of people, break-ups, etc. I don’t have too many standard go-to songs that I listen to. And it’s been a while since I broke up with anyone… more than 10 years! But there are a few that pop into my head … Sheryl Crow – The First Cut is the Deepest. Indigo Girls – Ghost. The break-up song in La Boheme (I know, I’m sorry, that is so dorky but it’s true).

    This post was interesting to me especially following our offline conversation about your essay. It really is like a breakup. I still can’t confront some of my friend breakups, and there are songs that remind me of those people, too!
    Deb @ Urban Moo Cow recently posted…Five Things I Will NOT Miss About Brooklyn (A Rant)My Profile

  5. I miss mix tapes; somehow the iTunes playlist, or even the mix CD, doesn’t strike the same chord as that struggle to see if you had enough room left to put one-more-song on side A. One of my favorite mix tapes ever was a break-up mix my now-husband made for me during our junior year in college when I rejected his romantic advances and started dating his roommate. (Oh well, all’s well that ends well.) Now *that* was a great mix, featuring several of the songs you mention above! 🙂
    Kristen @ Motherese recently posted…He’s a Poet and He Doesn’t Know It?My Profile

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