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.
Sep. 1, 2011
Stephanie Georgopulos is/was/forever will be from Brooklyn, NY.

“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

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  • Guts

    Casimir Pulaski Day – Sufjan Stevens

  • http://sparkplugminuet.tumblr.com Anna Gustafson

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

  • Anonymous

     I’d Rather Go Blind–Etta James

  • 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. 

  • 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. 

  • http://www.facebook.com/profile.php?id=24703745 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.

  • Lesbian

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

  • http://twitter.com/miatard mia
  • Kelcie Moseley

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

  • http://other-worldly.org Justine

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

  • http://www.facebook.com/people/Steven-Fiveoseveniam-Lazaroff/7706828 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

  • Anonymous

    Oh, man, that is so true.

    Also, Make You Feel My Love.

  • http://www.nosexcity.com NoSexCity

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

    i mean… um…

  • http://www.nosexcity.com NoSexCity

    sooooo good.

  • Guest

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

  • 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.” 

  • http://www.facebook.com/jessi.smith1 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.

  • 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. 

  • Anonymous

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

  • Anonymous

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

  • http://www.facebook.com/profile.php?id=612928768 Samie Rose

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

  • http://www.facebook.com/profile.php?id=612928768 Samie Rose

    lolololol

  • http://www.facebook.com/profile.php?id=690741901 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”

  • http://www.facebook.com/profile.php?id=23900040 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

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

  • Diana Salier

    third eye blind – deep inside of you

  • diana Salier

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

  • http://twitter.com/tannnyaya 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

  • http://allirense.com Alli

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

  • Heyoh

    noooo Halleluja by Jeff Buckley. Infinitely better and 1000x more likely to make you cry

  • Devin

    Don’t Think Twice It’s Alright by Bob Dylan and Butterfly by Weezer and Lover You Should Have Come Over by Jeff Buckley and (this is my guilty pleasure, depth of sorrow song) Last Kiss By Taylor Swift. Cry away, peeps.

  • Arowe1011

    Leonard  Cohen Leonard Cohen Leonard Cohen 

  • Guest

    I love you

  • http://twitter.com/ihatewheat Robin

    YESSSS

  • http://twitter.com/ihatewheat Robin

    Mine is Survivor “The Search is Over”

  • http://twitter.com/lauren_wilford Lauren Wilford

    Admit it. You were totes into the soundtracks for “Garden State” AND “The Lass Kiss.” 

  • http://twitter.com/lauren_wilford Lauren Wilford

    Admit it. You were totes into the soundtracks for “Garden State” AND “The Lass Kiss.” 

  • Um

    BON IVER’S “MICHICANT” IS THE ONLY ACCEPTABLE SONG TO CRY TO

  • http://twitter.com/dianasalier diana salier

    the entirety of “for emma, forever ago”

  • http://twitter.com/dianasalier diana salier

    YES

  • http://twitter.com/dianasalier diana salier

    PERFECT SONNET

  • Elizabeth Whalley

    Oh, this is so completely fantastic and perfect. Saving this…also, stay out of my head.

  • Klara

    I don’ t care what you call me – David Ford.
    I would die for you – Matt Walters.
    So let go – The Good Life

    You-tube away kids, they’re tear jerkers.

  • http://twitter.com/melvinismad Melvin Alvarez

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

  • Rachel

    Ugh, I have seven separate playlists of crying music (yikes?) but these songs are the best:

    A Case of You – Joni Mitchell (also anything off of Blue)
    Blake’s View – M. Ward
    Don’t Let Me Down – The Beatles

  • http://www.facebook.com/jessi.smith1 Jessi Smith

    Oh, and, also… William Fitzsimmons, anyone? Makes me wish I were capable of growing a really fantastic beard to soak up my tears.

  • Rhee

    Also, The Funeral by Band of Horses

  • Guestropod

    BOTH SIDES NOW

  • jen

    Almost Lover – A Fine Frenzy
    Little Hell – City & Colour
    And just anything, anything sung by Matt Walters.

     

  • jen
  • a.

    Came here to say that.

  • http://www.nosexcity.com 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…

  • Vicky Shazam

    uhm, also any album by The Smiths (mostly The Queen is Dead) makes me wanna die when i’m sad. yeah.

  • martin

    Falling Awake by Gary Jules, best sad song period!

  • douchegirl

    Bearded folk singers FTW!

  • douchegirl

    :(

  • 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?”

  • douchegirl

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

  • douchegirl

    “The Trapeze Swinger” Iron & Wine. 

  • Cathy

    The Brokeback Mountain theme song.
    It’ll break your heart in seconds.

  • Cassmf

    My altimate tear fest playlost includes: 
    to build a home – cinematic orchestra
    I have nothing – Noah and the Whale
    Don’t be afraid you’re already dead – Akron/family 
    U2 cover – With or without you – Hamish Cowan And when Im in a sad crying rage – new york, I love you but you’re bringing me down – LCD Soundsystem 
    They get me everytime.  

  • Bee

    for me it’s martha by tom waits, “and I was always so impulsive/ I guess that I still and/ but all that really mattered then/ was that I was a man/ I guess that our being together was never meant to be/ but Martha, Martha/ I love you can’t you see” I guess the best time to listen to this would be after you know you’ve let something go too far and you don’t know how to make things right. 

  • http://www.twitter.com/mexifrida Frida

    ditto on almost lover. i used to cry to that when i had it on my ipod.

  • http://www.twitter.com/mexifrida Frida

    For me it’s Wonderful World by James Morrison, Maps by the Yeah Yeah Yeahs, Let’s Not Shit Ourselves (To Love and to be Loved) by Bright Eyes, A Line Allows Progress A Circle Does Not by Bright Eyes, Warwick Avenue by Duffy, and When You Were Young by The Killers, for some reason too.  
    I hate knowing I’m 100% going to cry if I’m alone listening to them, but it seems like it needs to be done sometimes when you just want to release and cry about whatever is happening.

  • lala

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

  • Mel

    Make Up Smeared Eyes by Automatic Loveletter. Almost everything by Automatic Loveletter.

  • ANONYMOUS

    Don’t Confess – Tegan and Sara

    Lyrics that make you lose it: And every second I spend waiting drags me closer to this grave/No I’m not alone, I’m just on my own/And I, it’s a little cold outside/And don’t be so hard on yourself, you won’t get better till you get worse/Send a little love my way

    When to listen: When you feel all alone in inexplicable misery.

  • Te.

    Racheal Yamagata’s The Reason Why gets me every fucking time. 

  • Claire

    Joni Mitchell – Case of You. never fails.

  • devin

    my boyfriend and I just broke up. I went through all of the comments and bought several songs on itunes. tonight’s gonna suck and I’m ready for it. 

    also, I forgot to mention last week….TRY ME by James Brown is probably the best. Walk Away by Ben Harper. Fuck.

  • pesto

    most Bright Eyes, anything off the Antler’s first album, annnnnd Adele. ugh Adele. she occasionally makes me cry when I’m not even sad

  • http://twitter.com/wearewere Olivia

    Sufjan Stevens – Romulus

    (first song I noticed that I would tear up every single time I heard it)

  • merh

    I find Stevie Wonder’s “Lately” song to be heartbreaking/ fueling the waterworks. The lyrics that get me are ” Well, I’m a man of many wishes/Hope my premonition misses/ But what I really feel my eyes won’t let me hide /‘Cause they always start to cry/ ‘Cause this time could mean goodbye”

    Went through many nights during a breakup sobbing to this one 

  • 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.

  • Leo9085861

    A really upsetting song I find is ‘Mad World’ by Gary Jules

  • xx

    this years love- david gray
    the scientist- coldplay

  • Rich

    I know this was written over six months ago, but…I got dumped today.  Will be listening to these on repeat for an indeterminate amount of time.

  • Rich

    oh, and “Simple Together” by Alanis Morissette.  Never fails.

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