Breakup Playlist


While nursing a broken heart, sometimes you’ve just gotta do something that will let you get all of the tears and hurt out. I’m a fan of the breakup playlist, the songs that I know will make me ugly cry until I’m exhausted, and my face is puffy and red. My girlfriend told me that her go to is a glass of wine and a sad movie, but I just think that music has the ability to connect to one’s soul in a way that a movie doesn’t.  Do you have a breakup playlist? Or do you have a certain song that will always make you cry? I’m interested in what everyone else is listening to!

Here are my top 20 breakup songs (with the one killer lyric that brings on the tears):

  1. ‘Please, Please, Please Let Me Get What I Want’ – Dream Academy (Cover)
    • Killer Lyric: Well, all of the lyrics are soul crushing. Morrissey, man; he’s one hell of a melancholy lyricist. This cover of the song by Dream Academy is especially haunting though, with the whispered singing of Nick Laird-Clowes, and the dreamy backup vocals of Kate St. John, lain over the melody being played by strings. It’s haunting, and WILL make you cry.
  2. ‘For a Little While’ – Langhorne Slim
    • Killer Lyric: “Days pass so fast; Night goes so slowly. Your spell has been cast; I’m laying lonely.” If you’ve never had the pleasure of listening to Langhorne Sim’s desperate, bluesy voice, I highly recommend you do so right away.
  3. ‘Lovesong’ – The Cure
    • Killer Lyric: “Whenever I’m alone with you, you make me feel like I am home again.” The sadness of this one is probably a little personal to me, as it is my ex’s favorite song. It’s a great tune, and Robert Smith comes close to Morrissey in terms of melancholy. Longingly sad, it’s just a great song.
  4. ‘Dreams’ – Fleetwood Mac
    • Killer Lyric: “But listen carefully to the sound of your loneliness; Like a heartbeat drives you mad; In the stillness of remembering what you had
      And what you lost, and what you had, and what you lost.” I’m not a big fan of Fleetwood Mac, but the history of this song is heartbreaking. Stevie Nicks wrote it while she was going through a breakup with Lindsay Buckingham. In response, he turned around and wrote “Go Your Own Way” for Nicks. What an asshole.
  5. ‘Hallelujah’ – Jeff Buckley 
    • Killer Lyric: “Maybe there’s a God above; All I’ve ever learned from love was how to shoot somebody who outdrew you. And it’s not a cry that you hear at night; It’s not somebody who’s seen the light, It’s a cold and it’s a broken Hallelujah.” Do I need to say more?  I don’t think so.
  6. ‘Angels’ – The xx
    • Killer Lyrics: “You move through the room; Like breathing was easy; If someone believed me they would be as in love with you as I am.” This song kills me every time I hear it. The time spent falling in love with someone is a double edged sword; it’s sweeter than anything at the time, but after it ends the thoughts of that time are gutting.
  7. ‘Willow Lane’ – Ryan Adams
    • Killer Lyric: “I thought I knew the right things to say; Thought I knew what would take you away; Thought I knew the right things to say; But you’re fadin’ away.” Quick confession: I start crying the moment that I hear Ryan’s tortured voice utter the first note it sings; every song, every damn time.  If you need an entire record of sad songs, I’d like to point you in the direction of Adam’s ‘Heartbreaker’.  He’s the king of the unrequited, lost love songs.
  8. ‘Comfortable’ – John Mayer
    • Killer Lyric: “Our love was comfortable and so broken in; She’s perfect, so flawless; I’m not impressed.” Think you’re ready to start dating again? Listen to this song, because you’re probably not. Apologies to the new girl in this song, who didn’t measure up to the love of John’s life. — I’m also able to distinguish Miles from Coltrain, just for the record.
  9. ‘From Eden’ – Hozier
    • Killer Lyrics: “Honey you’re familiar like my mirror years ago; Idealism sits prison, chivalry fell on it’s sword. Innocence died screaming, honey ask me I should know. I slithered here from Eden just to sit outside your door.” “Babe, there’s something broken about this; But I might be hoping about this.” If there was a song that perfectly summed up my feelings at this exact moment, it’s this one. Thanks, Hozier.
  10. ‘Wild is the Wind’ – Cat Power (Cover)
    • Killer Lyric: “You touch me; I hear the sound of mandolins. You kiss me; With your kiss my life begins. You’re spring to me, all things to me.” This song has been covered a million times, and for good reason. It’s a beautiful, beautiful song. I listened to it a lot when my ex and I first began dating, so it’s especially cutting for me to hear it.
  11. ‘One of Us Must Know’ – Bob Dylan
    • Killer Lyrics: “But, sooner or later, one of us must know, you just did what you’re supposed to do. Sooner or later, one of us must know, that I really did try to get close to you.” Bob is a poet, with an incredible way of writing lines that perfectly express what you’re feeling. He a son of a bitch of a guy, but damn, his prose is “right on target, so direct.”
  12. ‘Save Me’ – Queen
    • Killer Lyric: “Each night I cry, I still believe the lie: “I love you ’til I die””.  A great song for the dumpee.
  13. ‘Don’t Dream It’s Over’ – Crowded House
    • Killer Lyric: “Now I’m walking again to the beat of a drum, and I’m counting the steps to the door of your heart.” For those of us who have ever tried to get back a lost love, this is our song.
  14. ‘Tears Dry On Their Own’ – Amy Winehouse
    • Killer Lyric: “I wish I could say no regrets, and no emotional debts; Cause as we kiss goodbye the sun sets; So we are history; The shadow covers me;
      The sky above ablaze that only lovers see.” An upbeat tune with a depressing story. Oh, Amy….
  15. ‘Before I Go’ – The Juliana Theory
    • Killer Lyric: “She driving like me, She’s falling asleep, And she wrecks me. She wrecked me.” Well, this is technically a love song, I know because it was written about me. While it is reminiscent of a really wonderful time in my early 20’s, it is also a song of longing for someone who you want but you can’t have. Sometimes the timing just isn’t right.
  16. ‘Feels Like We Only Go Backwards’ – Tame Impala
    • Killer Lyric: “It feels like I only go backwards baby. Every part of me says go ahead. I got my hopes up again, oh no… not again. Feels like we only go backwards darling.” How many of us can relate to how it feels to hold onto to someone who isn’t sure about us? We lose ourselves in that person and wait around for them to want us.
  17. ‘Drew Barrymore’ – SZA
    • Killer Lyric: “I get so lonely, I forget what I’m worth; we get so lonely, we pretend that this works.” See above. It ain’t easy being the one with all the feelings.
  18. ‘Without You’ – Lana Del Rey
    • Killer Lyric: “But burned into my brain are these stolen images; Stolen images, baby, stolen images. Can you picture it, babe, the life we could’ve lived?” Frankly, I can’t hear a Lana song without turning into a puddle of tears on the floor. She has the most haunting voice I’ve ever heard, and her songs peppered the beginning of my relationship with my ex. Lana is all of us who long for someone.
  19. ‘Go Slow’ – Haim
    • Killer Lyric – “Go slow, so that I can hear everything you’re saying. Now I know you’re going. You just threw this away.” It’s possible to be sad and angry at the same time. That’s the joy of this confusing post-break up time. Thanks for making it sound just like my own hurt, Haim.
  20. Let It Go’ – James Bay
    • Killer Lyric: every single last one of them.



6 thoughts on “Breakup Playlist

  1. I have a list too, here’s a couple that play pretty regularly at the moment. I have a heap of really old ones too, but I’d be here all night lol xx
    Dont Wanna Think – Julia Michaels
    Too Good at Goodbye – Sam Smith
    Honest – The Chainsmokers
    Praying – Kesha
    Thanks for sharing, have listened tonight, awesome choices (though I couldn’t find The Juliana Theory) xx


    • Yay!!!! Thank you for the song suggestions! I just downloaded them all, and can’t wait to listen. My girlfriend has been preaching the greatness of Kesha’s ‘Praying’ for a month or so, she said it’s amazing. That Juliana Theory song is pretty impossible to find now, I think. It was a b-side track for an album from 2002/2003. It always makes me smile/cry, so it inevitably ends up on my ‘sad songs’ list. xoxo


  2. I have songs or sections of songs that mist me up, but they’re not related to break-ups, just to what I perceive as the inherent musical beauty of the piece. As a guy, I’ve lived through painful break-ups–my fault and not–and I usually just implode for however long the pain takes to go away. Not healthy and not recommended, but I’m a guy so it is what it is. Misty passages? Guitar solo in All Along the Watchtower by Hendrix. Most of Albatross by Fleetwood Mac. The Wind Cries Mary by Hendrix. Strange Fruit by Billie Holliday. MSOC

    Liked by 1 person

    • When I’m in my normal state, I agree that there are certain songs, for me, that bring about an emotional response simply because of their beauty. The entirety of Debussy’s ‘Children’s Corner’ and ‘Suite Bergamasque’ bring me to my knees each time I hear them. ‘Strange Fruit’ is a great recommendation. Billie’s voice was pure magic. Xoxo


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