A New Top 5 Most Heartbreaking Songs of the Past 20 Years Sep 13 '05    Write an essay on this topic. Tweet Popular Products in Music The Dirtchamber Sessions, Vol. 1 by The Prodigy From $11 Jersey Boys [Original Broadway Cast Recording] by Original Broadway Cast From $8 The Bottom Line Honorable Mention here for Elvis Costello/Burt Bacharach for God Give Me Strength about discovering an affair, and another Jann Arden song, When You Left Me. Despair at its zenith. I thought this was time for a re-vamp, though I did enjoy the previous poster's ePinions. Some of these may be quite obscure, nevertheless, I find them quite evocative, and all have made tears come to my eyes. 5. I Can't Make You Love Me - Bonnie Raitt. Sometimes, it's all about delivery. Bonnie Raitt's growl is sultry at times, fun at times, but until this song, I never heard her sound depressed and resigned and just.... sad. Key Lyrics: I'll close my eyes then I won't see the love you don't feel when you're holding me Cause I can't make you love me If you don't... 4. Crying - Roy Orbison, sung by k. d. lang. Though lang's soaring vocal is stunning, what's really wonderful is the way she took this great old song and breathed new life into it. The lyric deals with a lost love, or maybe even a love that never was... the meeting some time after the affair ended is poignant and touching. Key lyrics: I thought that I was over you But it's true, so true I love you even more than I did before But darling, what can I do? For you don't love me And I'll always be crying over you, crying over you 3. When Somebody Loved Me - Randy Newman, sung by Sarah MacLachlan Okay, so the song is actually sung by a doll, left behind as her beloved owner grew up. But YOU listen to it, and don't cry and I'll give you a cookie. Key Lyrics: Lonely and forgotten, Never thought she'd look my way, And she smiled at me and held me, Just like she used to do. Like she loved me, When she loved me. When somebody loved me, Everything was beautiful, Every hour we spent together, Lives within my heart. When she loved me.... 2. To Where You Are - Richard Marx/Linda Foster, sung by Josh Groban He's over-performed this song, but the emotive quality of his voice the first time I heard this song put Josh Groban on my list of People to Watch. If you've ever lost a loved one in this very painful way, the tenderness of delivery, the poignance of the lyrics, the hope of reunion in a life beyond are just... well, heartbreaking. Key Lyrics: Fly me up to where you are Beyond the distant star I wish upon tonight To see you smile If only for awhile To know you're there A breath away's not far To where you are 1. Leave Me Now (Hard Enough) - Jann Arden Jann Arden is my favorite Sad Girl With Guitar, a whole category of music to me. This song is just the saddest and most satisfying of all breakup songs, and most closely mirrors my own state of mind in the wake of the sad and unwanted dissolving of a cherished relationship. Though sad, once I was resigned to the fact the affair was over, I just wanted her to leave. It was over. Key Lyrics: I put the whole lyric here, because it's just so damn good. leave me now, don't hang around just close the door and leave the key under the plant outside the one you bought me years ago look how it's grown go away, you cannot stay here take your heart off of your sleeve and let me catch my breath i hope you haven't left a thing it's hard enough to be here without your love move along, you don't belong here wipe yourself off of my floor and let me get some sleep i cannot keep you in my heart it's hard enough to be here without your... love

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