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[Pick of the Week] Most Heartbreaking Songs

Since the dawn of music, there have been sorrowful songs.   Or maybe, since the dawn of sorrow, there has been music?  There's always a song, whether through the clarity of its instruments or the nature of its lyrics that can make any room awfully dusty...you may even shed a tear.  So, here goes:  The Most Heartbreaking Songs...ever! 10)  "Yesterday" - The Beatles (1965) "Yesterday, Love was such an easy game to play, Now I need a place to hide away, Oh, I believe in yesterday." 9)  "Hurt" - Johnny Cash (2002) This was originally written by Trent Reznor (of Nine Inch Nails) in 1994 off his album "The Downward Spiral."  At first, Reznor felt a little hesitant about having Johnny Cash covering his song.  But... "I pop the video in, and wow… Tears welling, silence, goose-bumps… Wow. [I felt like] I just lost my girlfriend, because that song isn't mine anymore… It really made me think about how powerful music is as a medium and art form. I wrote some words and music in my bedroom as a way of staying sane, about a bleak and desperate place I was in, totally isolated and alone. [Somehow] that winds up reinterpreted by a music legend from a radically different era/genre and still retains sincerity and meaning — different, but every bit as pure." -Reznor, on Johny Cash covering "Hurt" 8)  "Clair De Lune" - DeBussy (1905) You've probably heard this song in a variety of different movies (probably most notably in the ending scene of "Ocean's 11").  It's the third movement of Suite bergamasque by Claude Debussy, first published in 1905.    The title comes from a poem of Paul Verlaine's of the same name. 7)  "Unchained Melody" - Righteous Brothers (1955) This song probably conjures up images of a sweaty Patrick Swayze and Demi Moore in the movie "Ghost."  It was written by Alex North and has lyrics by Hy Zaret.  It's been covered more than 500 times by all types of different bands and in many different languages.  I like to think it eloquently puts a universal theme of love and longing: "Oh my love, my darling I've hungered, Hungered for your touch A long lonely time, And time goes by so slowly And time can do so much, Are you still mine?" 6)  "I'm So Lonesome I Could Cry" - Hank Williams (1949) This song was written by Hank Williams and believed to be inspired by his troubled relationship with wife Audrey Sheppard.  Here are some of the lyrics: "The silence of a falling star Lights up a purple sky. And as I wonder where you are I'm so lonesome I could cry." 5) "Mad World" - Gary Jules (2001) This original song is by Tears For Fears and it was covered by Gary Jules and Michael Andrews for the soundtrack to the movie "Donnie Darko." "Went to school and I was very nervous No one knew me No one new me Hello teacher tell me what’s my lesson Look right through me Look right through me" 4) "Wreck of the Edmund Fitzgerald" - Gordon Lightfoot This is a heartbreaking long song by Gordon Lightfoot commemorating the SS Edmund Superior that sunk on Lake Superior in 1975. "The church bell chimed till it rang twenty-nine times For each man on the Edmund Fitzgerald. The legend lives on from the Chippewa on down Of the big lake they call 'Gitche Gumee'. Superior, they said, never gives up her dead When the gales of November come early" 3)  "Tears in Heaven" - Eric Clapton (1992) This sad tale about Clapton's four-year-old son Conor who fell from a window on the 53rd floor of a New York apartment is one of the most eloquent and tear jerking songs of all time. "Would you know my name if I saw you in heaven? Would it be the same if I saw you in heaven? I must be strong and carry on, 'Cause I know I don't belong here in heaven." 2) "Last Kiss" - Pearl Jam (1998) The original song was written by Wayne Cochran in 1961, but was later covered by Pearl Jam.  It is one of the most devastating songs to ever listen to.  I know my roommate in college never wanted to hear it, because he would always break down and cry if he did.   It's based on a story about a 16-year-old couple who was on a date around Christmas time when they collided with another car on the road. "I held her close, I kissed her our last kiss I found the love that I knew I would miss But now she's gone, even though I hold her tight I lost my love, my life that night." 1)  "Hallelujah" - Jeff Buckley This song was originally written by Leonard Cohen in 1984 and has seen numerous covers by all kinds of bands.  But, I think the one by Jeff Buckley featuring a soft guitar is the most haunting and melancholy, yet strangely beautiful. "Maybe there’s a God above But all I’ve ever learned from love Was how to shoot at someone who outdrew you It’s not a cry you can hear at night It’s not somebody who has seen the light It’s a cold and it’s a broken Hallelujah" Any Honorable Mentions? Let us know if you have any songs that are especially sad to you. -Soren Nieminen

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03/18/2011 11:36AM
[Pick of the Week] Most Heartbreaking Songs
Please Enter Your Comments Below
03/18/2011 12:40PM
Mary
I've always thought that "Hold On" by Sarah McLachlan is heartbreaking because it sounds like her lover is dying.
03/18/2011 1:46PM
Madtown Sam
I'd add "Brick" by Ben Folds...
03/18/2011 9:14PM
Scott Baltes
Dan Fogelberg - "Same Old Lang Syne" In my opinion, THE most depressing Christmas song, yet still one of my favorites.
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