15 of the Greatest Breakup Songs

Written by on December 1, 2021

When you’re going through a break-up, nothing hits quite like sad songs

And no song could be truly devastating without some heartbreaking lyrics. From Frank Ocean to Phoebe Bridgers, some artists just really seem to understand our occasional need, as listeners, to cry it out to a great piece of music. Let’s get into it!

First up, of course we have some Frank Ocean.

1. Bad Religion – Frank Ocean

Bad Religion” is definitely one song of Ocean’s that I’ve streamed on repeat — the slow pacing, the melancholic instrumentals, and the earth-shattering lyrics are addictive when you’re already feeling sad. The usage of his journey during a usually monotonous experience, a taxi ride, as a vessel for his heartbreak is a brilliant lyrical move.

It’s a, it’s a bad religion / To be in love with someone who could never love you.

“Bad Religion”, Channel Orange (2012)

2. Someone Great – LCD Soundsystem

LCD Soundsystem‘s entire Sound of Silver album is phenomenal, but two of its songs are genuinely devastating. “All My Friends” is heart-wrenching because it addresses the tragic parts of growing older, though, not because it’s about a breakup. “Someone Great” on the other hand? Hits the nail right on the head in that aspect.

There shouldn’t be this ring of silence, / But what are the options? / When someone great is gone.

“Someone Great”, Sound of Silver (2007)
LCD Soundsystem, courtesy of The Ringer

3. Les – Childish Gambino

Oh, Childish Gambino. This album (Camp, 2011) is gut-wrenching and a bop all at once. This specific song is the perfect combination of catchy and tragic; I’m not sure exactly why it’s so devastating to listen to after a breakup, but I can tell you from firsthand experience that “Les” is made for this list.

Nobody else matters girl and / We’re kissing in the bathroom … I hope nobody catch us / But I kind of hope they catch us anyway.

“Les”, CAMP (2011)

4. I Bet on Losing Dogs – Mitski

Most of Mitski‘s work is pretty melancholy, but this song is definitely made specifically for breakup listening. She illustrates a complex relationship, comparing it (and her past relationships) to betting on losing dogs. Maybe she just tends to root for the underdog, but it definitely sounds like she gets into relationships which are doomed from the start. “I Bet on Losing Dogs” is the perfect song for mourning a relationship that you realize probably should have just never happened.

Where I’ll be looking in their eyes when they’re down / I’ll be there on their side / I’m losing by their side.

“I Bet On Losing Dogs”, Puberty 2 (2016)
Mitski, Ebru Yildiz, courtesy of NPR

5. Terrence Loves You – Lana Del Rey

Terrence Loves You” is possibly the greatest heartbreak song of all time — or at least of Lana Del Rey‘s discography. Honestly, the whole Honeymoon (2015) album is pretty mournful in tone, but this song takes the cake for me. The achingly slow tempo is like salt in the wound when combined with the lyrics. It’s beautiful.

I lost myself when I lost you, / But I’ve still got jazz / When I’ve got those blues.

“Terrence Loves You”, Honeymoon (2015)

6. Drawn to the Blood – Sufjan Stevens

Sufjan Stevens’s album Carrie & Lowell (2015) primarily exists as a vessel through which Stevens grieved his absent mother’s passing. He’s stated in interviews that the year he spent writing this album was a pretty dark time, which makes sense given the album’s wrenchingly sad undertones.

Although most of the tracks focus on Stevens’s relationship with his mother and her death, this song (“Drawn to the Blood“) and a few others reflect on some unfortunate romantic situations, thus landing it on this list.

For my prayer has always been love / What did I do to deserve this now? / How did this happen?

“Drawn to the Blood”, Carrie & Lowell (2015)
Carrie & Lowell album art

7. Falling – Harry Styles

This album (Fine Line) is pretty cheerful, considering a fair portion of it is dedicated to an unpleasant breakup Harry Styles went through while writing it. This song, though, doesn’t really fit that definition. However, “Falling” is remarkably well-written and neatly encapsulates the feeling of being freshly post-breakup.

And I get the feeling that you’ll never need me again.

“Falling,” Fine Line (2019)

8. Skinny Love – Bon Iver

Bon Iver decided to really f*ck with us with “Skinny Love” (the third track of For Emma, Forever Ago). Not that the rest of the album is much of a pick-me-up. This song was actually released as the first single of this 2008 album, leading eventually to a masterpiece of a record, with its fair share of melancholy songs.

And I told you to be patient / And I told you to be fine / And I told you to be balanced / And I told you to be kind / And now all your love is wasted / And then who the hell was I?

“Skinny Love,” For Emma, Forever Ago
Part of For Emma, Forever Ago album cover

9. 20 Something – SZA

SZA’s second studio album, Ctrl (2017), was a phenomenon when it was released — and it still is. There were a couple strong contenders for this article off that album (see “Drew Barrymore,” “Garden (Say it Like Dat),” “Broken Clocks,” “Normal Girl“) but ultimately, “20 Something” won out for me. Also, it’s one of my sister’s favorites (bonus!).

Ain’t got nothing, running from love / Only know fear / That’s me, Ms. 20 Something.

“20 Something,” ctrl (2017)

10. I’d Have to Think About It – Leith Ross

The up-and-coming singer-songwriter Leith Ross dropped their two-track single I’d Have to Think About It earlier this year. The titular track, “I’d Have to Think About It,” aptly depicts the fear that sometimes follows a breakup, namely that you’ll never find someone like them again.

Things just won’t be the same … / But still I think about it.

“I’d Have to Think About It,” I’d Have to Think About It (2021)

11. ICU – Phoebe Bridgers

ICU,” a play on the phrase “I see you,” was the final single released for Phoebe Bridgers’ 2020 album Punisher. This song recounts her breakup with drummer/band member, Marshall Vore, and a moment she spent locked out of her house thinking about it. The spelling of ICU might also be a nod to the pain brought on by this breakup.

I don’t know what I want / Until I f**k it up.

“ICU,” Punisher (2020)
Phoebe Bridgers for Punisher, courtesy of High Road Touring

12. Shades of Cool – Lana Del Rey

Another Lana Del Rey heartbreak song — shocking, I know. This is one of my favorite tracks off of Ultraviolence because it so perfectly depicts the toll that interpersonal disconnection can take, especially in relationships. If you’ve ever had a seriously emotionally unavailable partner, you’ll get exactly what she’s talking about.

She sings about the feeling of being in love with someone she can’t “get through” to, and even though the relationship still exists, it seems like it won’t for much longer. If you’ve been “wronged” by someone who just doesn’t seem to care, “Shades of Cool” is for you.

But you are unfixable / I can’t break through your world, / ‘Cause you live in shades of cool, / Your heart is unbreakable.

“Shades of Cool,” Ultraviolence (Deluxe) (2014)

13. Loner – Kali Uchis

Kali Uchis‘ songs gravitate towards upbeat-pop tracks, but “Loner” off her EP Por Vida deviates widely from this precedent. This song, the 9th track on the EP, pretty much summarizes the bummed-out feeling which often accompanies a string of failed relationships.

Her disappointment in her most recent partner, though, seems to have provoked this particular song. Thus, she muses on the recent breakups she’s experienced through the lens of someone who wishes she hadn’t started dating again in the first place.

I was a loner until I met you / And I let you in after all the persuasion / Headaches and allegations.

“Loner,” Por Vida (2015)
Kali Uchis’ “Loner” music video thumbnail

14. No Children – The Mountain Goats

This is probably the darkest song in this article (which is saying something, especially with Lana Del Rey, Sufjan Stevens, and Phoebe Bridgers in here). However, though “No Children” is utterly bleak at face value, it’s actually full of quite a bit of hope — and maybe even irony. The juxtaposition of the “I hope you die” lyric with its inspiration, the song “I Hope You Dance,” kind of hints that the singer knows his distress isn’t all-encompassing, and there’s hope underneath the heartbreak.

You are coming down with me, / Hand in unlovable hand.

“No Children,” Tallahassee (2003)

15. Godspeed – Frank Ocean

Starting and ending an article about heartbreak songs with Frank Ocean seemed too appropriate not to do. So that’s what we’re doing; “Godspeed,” the second to last song on Frank Ocean’s iconic Blonde, is a killer track. Laden with samples (notably the outro) and his own ethereal vocals, Frank Ocean creates a cathedral of breakup-themed sorrow in this song. It truly is a remarkable feat.

Still, I’ll always be there for you / How I do / I let go of my claim on you / It’s a free world.

“Godspeed,” Blonde (2016)

Thanks for reading – make sure to save these tracks for a rainy day! And don’t worry, we’ll be writing more articles like this, so if heartbreak isn’t where you’re at, something more your speed will be published soon!

Frank Ocean promotional photo for Blonde

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