The 25 Most Exquisitely Sad Songs in the Whole World
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.
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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.
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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.
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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.
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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.
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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").
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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.
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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.
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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.
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- Filed under: Songs, The Hit List
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