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The 25 Most Exquisitely Sad Songs in the Whole World
- Posted by Spinner
25
'The River'
Bruce Springsteen (1980)
The Breakdown: Premature pregnancy, marriage and a weepy harmonica crush the dreams of a young couple.
The Waterworks: "We went down to the courthouse/And the judge put it all to rest/No wedding day smiles, no walk down the aisle/No flowers, no wedding dress."
Casualty Count: One couple's age of innocence.
The Waterworks: "We went down to the courthouse/And the judge put it all to rest/No wedding day smiles, no walk down the aisle/No flowers, no wedding dress."
Casualty Count: One couple's age of innocence.
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24
'Nothing Compares 2 U'
Sinead O'Connor (1990)
The Breakdown: In this Prince-penned purple ode to an incomparable ex, there is life after love, but life really sucks.
The Waterworks: "Nothing can stop these lonely tears from falling/Tell me baby, where did I go wrong?"
Casualty Count: One lover, seven hours, fifteen days.
The Waterworks: "Nothing can stop these lonely tears from falling/Tell me baby, where did I go wrong?"
Casualty Count: One lover, seven hours, fifteen days.
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23
'No Surprises'
Radiohead (1997)
The Breakdown: A killer even by Thom Yorke's bleak standards, the kiddie chimes can't hide the singer's suicidal depression.
The Waterworks: "I'll take a quiet life/A handshake, some carbon monoxide."
Casualty Count: One heart that's "full up like a landfill."
The Waterworks: "I'll take a quiet life/A handshake, some carbon monoxide."
Casualty Count: One heart that's "full up like a landfill."
22
'A Change Is Gonna Come'
Sam Cooke (1964)
The Breakdown: Recorded just before his tragic death, the soul great's response to 'Blowin' in the Wind' set the tone for the desperate Civil Rights struggle.
The Waterworks: "It's been too hard living, but I'm afraid to die."
Casualty Count: Countless proud citizens in Jim Crow America.
The Waterworks: "It's been too hard living, but I'm afraid to die."
Casualty Count: Countless proud citizens in Jim Crow America.
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21
'Space Oddity'
David Bowie (1969)
The Breakdown: In the same year as our lunar landing, rock's space alien creates Major Tom, whose remains will travel the galaxy alone forever.
The Waterworks: "Tell my wife I love her very much."
Casualty Count: One astronaut.
The Waterworks: "Tell my wife I love her very much."
Casualty Count: One astronaut.
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20
'That's the Way I've Always Heard It Should Be'
Carly Simon (1971)
The Breakdown: Marriage is inevitably dismal in this evocative pop hit, which was recorded a year before Simon's ill-fated marriage to James Taylor.
The Waterworks: "Their children hate them for the things they're not/They hate themselves for what they are."
Casualty Count: All marriages, one American dream.
The Waterworks: "Their children hate them for the things they're not/They hate themselves for what they are."
Casualty Count: All marriages, one American dream.
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19
'Lost Cause'
Beck (2002)
The Breakdown: The postmodern trickster reaches back to the Romantic era for the most depressing song on his breakup album, 'Sea Change.'
The Waterworks: "I'm tired of fighting/Fighting for a lost cause."
Casualty Count: The one love of your life.
The Waterworks: "I'm tired of fighting/Fighting for a lost cause."
Casualty Count: The one love of your life.
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18
'I've Gotta Get a Message to You'
Bee Gees (1968)
The Breakdown: Condemned man makes final plea to loved one.
The Waterworks: "One more hour and my life will be through."
Casualty Count: One convicted murderer with a heart of gold.
The Waterworks: "One more hour and my life will be through."
Casualty Count: One convicted murderer with a heart of gold.
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17
'Back to Black'
Amy Winehouse (2006)
The Breakdown: An ominous song of impending misery following infidelity, sung by a woman with her departing lover's name tattooed on her chest.
The Waterworks: "You go back to her/And I go back to black."
Casualty Count: A lover. Sobriety? Sanity?
The Waterworks: "You go back to her/And I go back to black."
Casualty Count: A lover. Sobriety? Sanity?
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16
'Shilo'
Neil Diamond (1968)
The Breakdown: Lonely kid turns to an imaginary friend.
The Waterworks: "Papa says he'd love to be with you/If he had the time."
Casualty Count: One squandered father-son relationship
The Waterworks: "Papa says he'd love to be with you/If he had the time."
Casualty Count: One squandered father-son relationship
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15
'My Mom'
Chocolate Genius (1998)
The Breakdown: Recent Springsteen sideman cut this heartbreaker about a return visit to his childhood home, and the mother he was losing to senility.
The Waterworks: "My mom, my sweet mom/She don't remember my name."
Casualty Count: One Alzheimer's victim (and one dog).
The Waterworks: "My mom, my sweet mom/She don't remember my name."
Casualty Count: One Alzheimer's victim (and one dog).
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14
'Anyone Who Had a Heart'
Dionne Warwick (1963)
The Breakdown: A lover begs her man to see how he's mistreating her. Classic Bacharach/David melodrama, crushing Warwick wails.
The Waterworks: "What am I to do?"
Casualty Count: One lover's sense of pride.
The Waterworks: "What am I to do?"
Casualty Count: One lover's sense of pride.
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13
'Naked as We Came'
Iron & Wine (2004)
The Breakdown: Indie folkie Sam Beam's brutally sweet love song acknowledging that one always has to die before the other, plus a plug for cremation.
The Waterworks: "If I leave before you, darling/Don't you waste me in the ground."
Casualty Count: Your better half.
The Waterworks: "If I leave before you, darling/Don't you waste me in the ground."
Casualty Count: Your better half.
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12
'In the Wee Small Hours of the Morning'
Frank Sinatra (1954)
The Breakdown: Ol' Blue Eyes parlayed his painful divorce from movie star Ava Gardner into a career makeover: the lonely guy at the end of the bar.
The Waterworks: "You'd be hers if only she would call."
Casualty Count: One Hollywood marriage, countless nights of sleep.
The Waterworks: "You'd be hers if only she would call."
Casualty Count: One Hollywood marriage, countless nights of sleep.
Getty Images
11
'Brick'
Ben Folds Five (1997)
The Breakdown: Singer recalls taking his high-school girlfriend to get an abortion -- on the day after Christmas, no less.
The Waterworks: "Now that I have found someone/I'm feeling more alone/Than I ever have before."
Casualty Count: One pregnancy, one first love, several Christmas presents.
The Waterworks: "Now that I have found someone/I'm feeling more alone/Than I ever have before."
Casualty Count: One pregnancy, one first love, several Christmas presents.
WireImage
10
'In the Real World'
Roy Orbison (1989)
The Breakdown: The master of pop-opera misery ('Crying,' 'It's Over') outdid himself with this quavering answer to his own 'In Dreams.' Posthumously released.
The Waterworks: "I love you and you love me/But sometimes we must let it be."
Casualty Count: All dreams.
The Waterworks: "I love you and you love me/But sometimes we must let it be."
Casualty Count: All dreams.
09
'Concrete Angel'
Martina McBride (2001)
The Breakdown: What's more devastating than a child's headstone?
The Waterworks: "A name is written on a polished rock/A broken heart that the world forgot."
Casualty Count: One victim of child abuse.
The Waterworks: "A name is written on a polished rock/A broken heart that the world forgot."
Casualty Count: One victim of child abuse.
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08
'Dance With My Father'
Luther Vandross (2003)
The Breakdown: Impossibly wrenching lament for the fact that we can't take care of our kids forever.
The Waterworks: "Sometimes I'd listen outside her door/And I'd hear how my mother cried for him/I'd pray for her even more than me."
Casualty Count: One father, one boy's sense of security in his father's arms.
The Waterworks: "Sometimes I'd listen outside her door/And I'd hear how my mother cried for him/I'd pray for her even more than me."
Casualty Count: One father, one boy's sense of security in his father's arms.
WireImage
07
'Hallelujah'
Jeff Buckley (1994)
The Breakdown: Leonard Cohen's existential hymn addressing an old fling becomes a heavenly, if unanswered, prayer in the hands of the ill-fated Buckley.
The Waterworks: "Love is not a victory march/It's a cold and it's a broken Hallelujah."
Casualty Count: One crisis of faith.
The Waterworks: "Love is not a victory march/It's a cold and it's a broken Hallelujah."
Casualty Count: One crisis of faith.
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06
'He Stopped Loving Her Today'
George Jones (1980)
The Breakdown: Sung by the country star with the most tears in his beer this side of Hank Sr., a jilted lover carries his old flame's memory until his dying day.
The Waterworks: "I went to see him just today/Oh, but I didn't see no tears/All dressed up to go away/First time I'd seen him smile in years."
Casualty Count: One fatally broken heart.
The Waterworks: "I went to see him just today/Oh, but I didn't see no tears/All dressed up to go away/First time I'd seen him smile in years."
Casualty Count: One fatally broken heart.
Getty Images
05
'I Know It's Over'
The Smiths (1986)
The Breakdown: For Morrissey, the world's loneliest singer, life isn't just over -- it never really began.
The Waterworks: "As I climb into an empty bed/Oh, well, enough said."
Casualty Count: One lonely soul ... any minute now.
The Waterworks: "As I climb into an empty bed/Oh, well, enough said."
Casualty Count: One lonely soul ... any minute now.
Getty Images
04
'Hurt'
Johnny Cash (2002)
The Breakdown: In failing health, the great American singer tolls a death knell for the rest of us with this brutal Nine Inch Nails song about addiction and self-destruction.
The Waterworks: "And you could have it all/My empire of dirt/I will let you down/I will make you hurt."
Casualty Count: Everyone he knows ("goes away in the end").
The Waterworks: "And you could have it all/My empire of dirt/I will let you down/I will make you hurt."
Casualty Count: Everyone he knows ("goes away in the end").
Getty Images
03
'Eleanor Rigby'
The Beatles (1966)
The Breakdown: The cute Beatle writes a timeless, devastating ode to the futility of life, set to a grieving string octet.
The Waterworks: "Eleanor Rigby died in the church and was buried along with her name/Nobody came."
Casualty Count: One spinster, one pair of socks.
The Waterworks: "Eleanor Rigby died in the church and was buried along with her name/Nobody came."
Casualty Count: One spinster, one pair of socks.
Getty Images
02
'Gloomy Sunday'
Billie Holiday (1941)
The Breakdown: The Queen of Soul-Sapping is haunted about losing a loved one.
The Waterworks: "Angels have no thought of returning you/Would they be angry if I thought of joining you?"
Casualty Count: One woman's will to live.
The Waterworks: "Angels have no thought of returning you/Would they be angry if I thought of joining you?"
Casualty Count: One woman's will to live.
Getty Images
01
'Chicken Wire'
Pernice Brothers (1998)
The Breakdown: Breathy Massachusetts sad sacks offer a lovely ballad about a woman choking to death on exhaust fumes ... and a cloud of minor chords.
The Waterworks: "They found her car/Still running/In the garage."
Casualty Count: One woman, and the drink she was holding.
The Waterworks: "They found her car/Still running/In the garage."
Casualty Count: One woman, and the drink she was holding.
Getty Images
- Filed under: Songs, The Hit List
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Add a Comment
As if
Hmmm.. "I can't make you love me" Bonnie Raitt. Tragic. Sad. Beautiful.
Wednesday at 1:28 AM Report abuse Permalink rate up rate down Reply
Tino Capello
Abortion doesn't kill pregnancy... it kills life!
Tuesday at 10:45 PM Report abuse Permalink rate up rate down Reply
Awad
Hurt is also a great song. I love Johnny cash 's version but nin's original much sadder and more powerful.
Saturday at 9:45 PM Report abuse Permalink rate up rate down Reply
Awad
Are you freaking kidding me? Nothing compares to you is the only song on the list which causes me to cry every time I hear it. Not only the saddest but one of the best songs of all time.
Saturday at 9:28 PM Report abuse Permalink rate up rate down Reply
That One Guy
No mention of "Diary" by Bread?
The words began stick and tears to flow.
Her meaning now was clear to see.
The love she'd waited for was someone else not me
Ouch - such a sweet sounding song, if you don't listen to they lyrics.
How can "Cats in the Cradle" not be on this list? I call shenanigans!
May 08 2013 at 8:06 PM Report abuse Permalink rate up rate down Reply
Cara
I Loves You Porgy, Miss Otis Regrets, Strange Fruit...
April 30 2013 at 10:07 AM Report abuse Permalink rate up rate down Reply"In the whole world" Hahahahahah Yep, right!
April 29 2013 at 5:07 PM Report abuse Permalink rate up rate down ReplySufjan Steven's "Casimir Pulaski Day" belongs near the top of this list.
April 25 2013 at 4:11 PM Report abuse Permalink rate up rate down Reply
JH
how can "Cats in the Cradle" not be on this list?
April 24 2013 at 8:37 AM Report abuse Permalink rate up rate down Reply
261 Comments