Mar 26 2009 10:57 PM ET

What's the most heartbreaking song of all time?

Heartbreaksongs_lOn the heels of the news today that our friends at Blender were shutting their doors, my pal Amanda, who was more than a little saddened by it, said that she’d turned to her iTunes in this time of need, and sent me an email asking me if I’d ever heard the song “Poke” by Frightened Rabbit. “Nope. Why?” She said it is the “most brutal” heartbreaking song of all time. She sent it over, and I listened. It’s sad for sure (if a bit weird: “And now we’re unrelated and rid of all the s— we hated/But I hate when I feel like this and I never hated you” — sad and creepy and mean but still sad!).

For my money, though — and I won’t get into specifics as to why, but no, it doesn’t have anything to do with it being on the High Fidelity soundtrack, thank you — it’s gotta be Smog’s “Cold Blooded Old Times.” Sample gut-punching lyric: “Though how can I stand/And laugh with the man/Who redefined your body?” Now whose rabbit is frightened, Amanda?!

Take a listen for yourself — and if this isn’t the most heartbreaking song of all time, Music Mix friends, then what is? (My colleague Leah Greenblatt insists it is either Love’s “Always See Your Face,” Spiritualized’s “Ladies and Gentlemen We Are Floating In Space,” or Elliott Smith’s entire catalog, but especially “A Fond Farewell.”)

Comments (1832 total) Add your comment
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  • outside agitator

    Jason, those songs you quoted aren’t sad…they’re crap. bad teen angst poetry. Tecumseh Valley…that’s a sad, timeless song. so’s Eleanor Rigby.

  • kepha2000

    I vote for “For No One” by the Beatles. Sample lyric “And in her eyes you see nothing – No sign of Love behind the tears – cried for no one – a love that should have lasted years…”

  • rc

    Joni Mitchell’s A Case of You

  • Alex

    It’s lesser known, but I can’t think of a more depressing, heartbreaking song than The Bravery’s “The Ocean.” Sample lyrics: “All of these moments are lost in time/ But you’re caught in my head like a thorn on a vine/ To forever torment me and I wonder why/ Do I wish i’d never known you at all?”

    • Natalie

      This is actually my favorite song, and it absolutely is one of the saddest I’ve ever heard.

  • Jara

    My Father’s House – Bruce Springstein
    Ever heard this bathroom-recorded demo acoustic track from The Boss’s seminal-for-song-writing Nebraska. This is one of the saddest songs I’ve ever heard, (about someone who has lost touch with their father over the who attempts to reconnect in a time of need and finds that he has passed)
    Oliver James by Fleet Foxes is pretty damn sad as well. The man and his guitar song is about a married couple who find their son drowned in a river after they let him play. (tell me that’s not a situation for FML)

  • Anonymous

    “Tears in Heaven” by Eric Clapton

  • Snarf

    “Song to the Siren” – This Mortal Coil
    The whole song uses metaphors and synonyms, and as for Liz Fraser’s vocals…chills.

  • Ruben

    Mine has to be “You Look So Fine” by Garbage. It’s haunting. Sample lyrics: You look so fine/I want to break your heart/And give you mine
    You’re taking me over/Knocked down/Cried out/Been down just to find out/I’m through/Bleeding for you

  • CalvinNHobbes

    Hmm…
    “Album of the Year” by The Good Life
    “A Gentleman Caller” by Cursive
    “Can’t Help Falling In Love” by Elvis
    “Ghost of an Unkissed Kiss” by Trembling Blue Stars
    “Anything You Want” by Spoon
    “Leap Year” by Maria Taylor
    “I Will Keep The Bad Things From You” by The Damnwells
    “Last Goodbye” by Jeff Buckley
    “It Ends With a Fall” by Okkervil River
    “When You Were Mine” by Prince
    “Strange Currencies” by REM
    “Come Pick Me Up” by Ryan Adams
    “The Size of Our Love” by Sleater-Kinney
    “Left and Leaving” The Weakerthans
    “These Arms Of Mine” by Otis Redding
    “Saving All My Love For You” by Tom Waits

    • harry

      if you’re hearts not in it by westlife

    • shellibelli

      yes!i just posted Last Goodbye by Jeff Buckley!

  • Blaise

    erm..unbreak my heart by toni braxton, surely that’s heartbreaking
    Ive recently just listened to ‘Alway’s by bon Jovi, surely some good rock ballads need to be included

  • celestialfrog

    Two saddest songs I can think of:
    “SLow Dancing in a Burning Room” -John Mayer
    “I Can’t Make You Love Me” -Bonnie Raitt
    Both songs are just heart-crushers.

  • Nicole

    A Song For You by Leon Russell…. As honest and heartbreaking as it gets…

  • jimmy

    he stopped loving her today by george jones…

  • kbarrett

    “I Can’t Make You Love Me” Bonnie Raitt

  • Kate

    “Dance With My Father” by Luther Vandross.

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