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The 25 Most Exquisitely Sad Songs in the Whole World: No. 25

There's no shortage of sad songs about rainy days and lovers who don't bring flowers. And then there are songs that truly bring the pain -- songs so despairing they can make us wonder why we even bother. Here are 25 little ditties so crushing, they could knock Dick Cheney to his knees.


'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.

Next Song

Listen to 'The River

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Posted by Spinner Staff
Filed under: Songs, The Hit List

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  • Comments (1043)

Reader Comments(1 of 53)

vote downvote upReportHigh Ranked

debbieat 5-05-2007

The River came out my freshmen year in college. Bought it, played it over and over till I knew every word and then I got to see him on that tour and it was the first time I saw Springsteen live. Still one of the best shows I have ever been to in my life. Great album. One my top 5 of all time!!! Plus it was a double album!!!

Reply
vote downvote upReportNeutral

Phyllis Giroudat 5-05-2007

I simply cannot believe that none of you could remember the saddest song ever. It was by Hank Williams and it's called "I'm so lonesome I could cry". Nothing can compare to that. His lyrics come pretty close to Shakespere. Just listen to it.

Reply
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d.j. andyat 5-05-2007

"He Stopped Loving Her Today" by: George Jones(1978) gets my vote.

Reply
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cnoeat 5-05-2007

Like I said, The sad songs are just that, SAD, and yup we do have our favorites, the one that is playin. LOL

Reply
vote downvote upReportHigh Ranked

R. Cooperat 5-05-2007

Hank Williams' "I'm So Lonesome I could Cry" and
George Jones "He Stopped Loving Her Today" are at the
top of my Sad Songs playlist.

Reply
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Lillianat 5-05-2007

I agree about "I am so lonesome I could cry". It was also done by B. J. Thomas. I like his version too.

Reply
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Philat 5-05-2007

"Don't take the girl" by Tim McGraw, that one makes me choke up.

Reply
vote downvote upReportHigh Ranked

Moodyat 5-05-2007

Phyllis - you gotta hear "I'm So Lonesome I Could Cry" sung by the Cowboy Junkies. That'll make you take to your bed for a week.

Reply
vote downvote upReportLow Ranked

cathy baggarlyat 5-05-2007

THE SADDEST DAY GETING ON AOL IN THE US AND IT ALL BEING IN SPANISH What the hell man

Reply
vote downvote upReportHighest Ranked

Michaelat 5-05-2007

"He Stopped Loving Her Today" by George Jones. One of the greatest and saddest songs of all time.

Reply
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walter earlesat 5-05-2007

are you washed in the blood? jesus shed his blood for us.how much sader can that be?

Reply
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Rupert Terryat 5-05-2007

old shep by Elvis Presly was a pretty sad song also

Reply
vote downvote upReportHighest Ranked

Salvoat 5-05-2007

Try this lyric on for size from Susan Werner's "Last of the Good Straight Girls" cd: "Passion's always half impossibility, but lovers that we lose we never dare forget - we visit them in mourning, in December and in May, at the graveyard of St. Mary's of Regret."

Reply
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Debraat 5-05-2007

Hmmm..some are good, but not top 25. How could you not have "Dust in the Wind" or "Tell Laura I Love Her" or "Last Kiss" or "Cat in the Cradle" or "Is That All There Is?"

Reply
vote downvote upReportNeutral

Philat 5-05-2007

"Don't take the girl" by Tim McGraw.
That one gets me all choked up.

Reply
vote downvote upReportHighest Ranked

R. Kliszat 5-05-2007

George Jones "He Stopped Loving Her Today" runs neck to neck with Meryl Haggard's "Kern River": "...it was there that I met her, it was there that I lost her -- I may drown in still water but I'll never swim Kern River again...."

Reply
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Loisat 5-05-2007

When I first heard "With Pen In Hand" by Vicky Carr I was driving home from work and had to pull to the side of the road because I couldn't see through my tears.

Reply
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Kattieat 5-05-2007

MY HEART WILL GO ON by celine dion. duh. no debate.

Reply
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Chadat 5-05-2007

Conway Twitty, That's my job. If you have ever had a father, you have to love this one

Reply
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Sheilaat 5-05-2007

I can't believe you didn't include "In The Ghetto" by Elvis Presley, or "Honey" by Bobby Goldsboro.

Reply
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