Apr 16 2009 08:15 PM ET

EW's 50 Most Heartbreaking Songs of All Time

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Last month, EW’s Jason Adams put up a post on the Music Mix asking “What’s the most heartbreaking song of all time?” and naming Smog’s Read the full post.

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  • LT

    diverse list, good job. i prefer the nina simone cover of ‘who knows where the time goes’ but the original is just as good. Also, radiohead’s true love waits or last flowers.

  • Saphira

    Never Grow Up by Taylor swift always makes me cry.

  • mike

    Patty Smyth’s delivery and the backbeat of “I Should Be Laughing” hit each and every sweet spot of self mocking heartache.

  • Ainara

    WOW! Most of the songs are good, but how the hell is Pearl Jam’s “Black” not included in this list?! Listen to the lyrics, and Eddie Vedder’s voice on MTV Unplugged is beautiful and full of emotion. Plus, the last verse “I know someday you’ll have a beautiful life, I know you’ll be a sun in somebody else’s sky,but why, why, why can’t it be, why can’t it be mine?” is probably the most heart breaking lyric ever. This song should be included!

  • Kathy

    Hello boys 2 men anyone

  • Ainara

    What about “Black” by Pearl Jam!? That song is heartbreaking, not only because of the lyrics, but the way Eddie sang it on MTV Unplugged was so full of emotion that it bring you to tears, it’s simply beautiful. Especially the last verse, I mean that verse is imortal.

  • Kaylee

    I would have included Hate Me by Blue October and Bother by Stone Sour. Those songs always make me bawl

  • Jordan

    Surprised there is no Smiths songs on here, and I think New Dawn Fades by Joy Division should be on here too

  • Joyce at I Take Off The Mask

    Thank you for sharing this, keep us posted with more relevant articles.

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