Great Songs To Cry To

If there’s a better way to spend my time other than forcefully making myself cry via tearjerking musical marathons, I don’t want to know what it is. (JK – send help.) Everyone should cry once in a while. It’s cathartic and fun, even! Here’s a brief guide to listening to my favorite cry jams, in no particular order. Take a listen if you’re trying to feel feelings or whatever. Disclaimer – some of these songs are covers, which I am well-aware of. I chose what I feel to be the most depressing rendition of said songs.

“Only Living Boy in New York” – Simon and Garfunkel

The lyrics that make you lose it: Hey, I’ve got nothing today to do today but smile
When to listen: When feeling terminally lonely

“With or Without You” – U2

The lyrics that make you lose it: My hands are tied/She’s got me with/Nothing to win and/Nothing left to lose
When to listen:
When you know that thing with that person you love is over

“Without You” – Harry Nilsson

The lyrics that make you lose it: No I can’t forget this evening/Or your face as you were leaving/But I guess that’s just the way the story goes
When to listen:
When you’re already in the middle of a sobfest and feel like amping up the waterworks

“Hallelujah” – Rufus Wainwright

The lyrics that make you lose it: Maybe I’ve been here before/I know this room, I’ve walked this floor/I used to live alone before I knew you/I’ve seen your flag on the marble arch/love is not a victory march/It’s a cold and it’s a broken hallelujah
When to listen: The first time there’s no question that your heart is broken

“All Cried Out” – Allure & 112

The lyrics that make you lose it: Apology not accepted/add me to the broken hearts you’ve collected
When to listen: When you’re kind of just joking about being upset but secretly hope that you’ll shed a few tears

“The Reason Why” – Rachel Yamagata

The lyrics that make you lose it: So, steal the show, and do your best/To cover the tracks that I have left/I wish you well and hope you find/Whatever you’re looking for
When to listen: When ambition has torn something apart

“The Greatest Love of All” – Whitney Houston

The lyrics that make you lose it: I decided long ago, never to walk in anyone’s shadows/If I fail, if I succeed/At least I live as I believe/No matter what they take from me/They can’t take away my dignity
When to listen: LOL. I’m sorry for including this song, but I think it’s great for crying when you’re down on yourself and feel like whatever you’re doing isn’t enough and you just need Momma Whitney to be like, “You can do it, girl!” Uh… maybe that’s just me.

“Year of the Cat” – Al Stewart

The lyrics that make you lose it: But the drum-beat strains of the night remain/In the rhythm of the new-born day/You know sometime you’re bound to leave her/But for now you’re going to stay/In the year of the cat
When to listen: When you’ve lost control and think that something beautiful can fix it

“Graceland” – Paul Simon

The lyrics that make you lose it: She comes back to tell me she’s gone/As if I didn’t know that, as if I didn’t know my own bed/As if I’d never noticed the way she brushed her hair from her forehead/She said, “Losing love is like a window in your heart/Everybody sees you’re blown apart/Everybody feels the wind blow.”
When to listen: When you realize that heartbreak can be carried around in the daylight TC mark

image – binusarina


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  • Guts

    Casimir Pulaski Day – Sufjan Stevens

    • Anonymous

      Oh, man, that is so true.

      Also, Make You Feel My Love.

  • Anna Gustafson

    yessss. good list. I would also add “I Can’t Make You Love Me” by Bonnie Raitt. Damn. that song hurts.

    • Kelcie Moseley

      I really do almost cry every time I hear that song. And almost everything by Joni Mitchell.

    • Melvin Alvarez

      everything goes dark and eerie when I hear that song. Not to mention hearing a weeping kitten in the background.

  • Anonymous

     I’d Rather Go Blind–Etta James

    • NoSexCity

      sooooo good.

  • lauren

    rilo kiley- rest of my life and science vs romance, also, tanita tikaram, valentine heart.  i have whole other lists in case its gloomy out, for summer crying, winter crying. i’ve shared this with my significant other, he’s cool with it. 

    • NoSexCity

      post on the internet so the rest of us have weepy-music at the ready for not having boyfriends.

      i mean… um…

      • lauren

        hold the phone, i said significant other, meaning, like he’s around and a guy he’s not “ready to be in a relationship” i got plenty to cry about. maybe him seeing my itunes and spotify mixes is what made that happen. 

      • NoSexCity

        When I think of the S.O. term it makes me think they’re around “for serious”. Still think you should share that crybaby playlist or two for the rest of us…

      • douchegirl

        Omg, I feel you so much. I had one of those “significant others”. Completely exhausted all my crying songs.

  • Sex Mahoney

    Other than radio they play in supermarkets and elevators, you don’t hear much about Al Stewart anymore, but I saw him play a church with a midget last year.

  • Sex Mahoney

    Other than radio they play in supermarkets and elevators, you don’t hear much about Al Stewart anymore, but I saw him play a church with a midget last year.

  • Elizabeth

    Every time someone covers “Hallelujah” by Leonard Cohen a kitten dies. 

    It should be a capital crime. 

    • Guest

      I love you

  • Carleigh Anne Mahaffey

    Oh shit, you got me with “Graceland.” My always-cry Paul Simon song is “Adios Hermanos”

  • Kelcie Moseley

    Where’s “Fix You”? That’s been in at least 8573784 sad scenes on television.

    • Anonymous

      I came here just to add “Fix You.” Holy shit that’s a great crying song.

      • lala

        me too. “when you love someone and it goes to to waste… could it be worse?” makes me teary every time. 

      • Iamsoy

        Haha I kept scrolling and scrolling looking for “Fix You” and finally used auto-find. Lightsss will guiddee you hoome…  UGH! I just got goose bumps typing that out.

  • Lesbian

    Where the fuck is Adele in this list? I feel like she strictly writes her songs to make the listener weep.

    • Guest

      “Someone Like You” could make me cry in a second on the happiest day of my life.

    • douchegirl

      When I was going through the worst part of my break up I listened to Adele’s “21” album from the moment I woke up to the moment I went to bed. “Don’t you remember” is the worst one.

      “When will I see you again?”

  • mia
  • Justine

    Dang. So on point with With Or Without You, The Reason Why and Hallelujah. Definitely my top crying songs.

  • Steven Fiveoseveniam Lazaroff

    i like it. a personal favorite (?) of mine is ‘a stone’ by okkervil river.

  • lia marie

    um again, where is bright eyes. dghjkl

    • Samie Rose


    • diana salier


  • Abby

    Fuck Was I, Jenny Owen Youngs.  “Love grows in me like a tumor/parasite bent on devouring it’s host/I’m developing a sense of humor/’til I can laugh at my heart between your teeth/’til I can laugh at my face beneath your feet.” 

  • Jessi Smith

    Pretty sure I’ve cried my way through the entirety of Damien Rice’s “9” album, which probably makes me a cliche, but, eh. You’ll get that.

  • Anonymous

    Carolina by M. Ward or Slim Slow Slider by Van Morrison or I Was Young When I Left Home by Bob Dylan

  • Samie Rose

    I started sobbing just by reading the song titles. ;-;

  • Kathy Ursua

    Come on, how come Sinead O’Connor’s “Nothing Compares 2 U” is not on the list? I really find it a very sad song. I’d also like to add Jewel’s “You Were Meant For Me”

    • Diana Salier

      hell yes to sinead. my ex and I used to sing that song as an ironic thing and now it ain’t so funny

      • douchegirl


    • Robin


  • Michelle Jackson Gamradt

    Mona Lisas and Mad Hatters- Elton John, Mexico- Cake, and Breathe Me- Sia, Save Me- Aimee Mann are good cry songs as well.  Good list!

  • Diana Salier

    third eye blind – deep inside of you

  • diana Salier

    third eye blind – deep inside of you
    beck – lost cause

  • Tanya Salyers

    I always cry to Cat Power.

  • ryan chang

    spot on with harry nilsson. i would also like to publicly divulge crying to nazareth’s cover of ‘love hurts’ simultaneously indulged the pleasure of crying while also making me stop crying because of how ridiculous i seemed to myself listening to the cover in the first place

  • Alli

    Allure! That brings me back to middle school days. What happened to them?

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