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The 25 Most Exquisitely Sad Songs in the Whole World

spinner.com — 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.

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  • andritchie, on 10/12/2007, -2/+127No Tears In Heaven?
    • thetanbark, on 10/12/2007, -24/+3No "Lush Life" by Billy Strayhorn? As sung by Dianne Reeves, this has to be one of the best and most saddist songs I've heard. See if you agree with me.

      MP3: http://www.sendspace.com/file/avgm71
      Lyrics: http://www.lyricsfreak.com/n/nat+king+cole/lush+life_20098063.html
    • msikma, on 10/12/2007, -2/+69"Tears in Heaven" is about Clapton's 4 year old son Conor, who fell from the 53rd-story window of his mother's New York City apartment. I too am surprised that it's nowhere to be found on this list.
    • MtnXfreerider, on 10/12/2007, -22/+1http://www.metacafe.com/watch/553833/adobe_photoshop_cs3_tutorial_emo_arm_cuts_trick_friends/
      THe video alone is emo... the music just finishes it off.
    • coollettuce, on 10/12/2007, -3/+50No Cats in the Cradle?
    • numb, on 10/12/2007, -1/+11I really expected Long Black Veil to be in there. I thought the live version with Dave Matthews and Emmy Lou Harris was pretty haunting (as well as sad.)
    • Bobombom, on 10/12/2007, -27/+17Funny how all the songs are in English...
    • norbiu, on 10/12/2007, -12/+7And what about Israel Kamakawiwo Ole's version of Somewhere over the rainbow ?
    • vypergts, on 10/12/2007, -1/+36Rainbow Connection by Kermit the Frog
    • Paranoidmarvin, on 10/12/2007, -6/+1I had a feeling Gloomy Sunday would be in there.
      aka "the Hungarian Suicide Song"
    • Twoodge, on 10/12/2007, -7/+2That's the Way, Zeppelin, should have been on the list.
    • MiddleOfNowhere, on 10/12/2007, -7/+2Elvis Costello: "I want you"

      I want you
      You’ve had your fun you don’t get well no more

      I want you
      Your fingernails go dragging down the wall
    • radu79, on 10/12/2007, -18/+2*****, the most sad song ever is: Offspring - Gone Away.
      Then there is Iron Maiden - For the Greater Good of God
    • PueSi, on 10/12/2007, -6/+1The Wreckroom by Loose Fur is my personal favorite, the music is so beautiful yet so depressing.
      Jim O'Rourke+Jeff Tweedy+Glenn Kotche you can lose.
    • r00tus3r, on 10/12/2007, -10/+4No mention of Rolling Stones - Paint it Black ??? !!!
      Is this guy for real?
    • TDot1980, on 10/12/2007, -8/+31This is a craptastic list. I've never heard of half the artists. Another one they missed was "Vincent" by Don McLean. I get goosebumps every time I hear the first few words "Starry, starry night..." For those unfamiliar, it's a song about Vincent Van Gogh and his troubled life. Best line: "And when no hope was left in sight / on that starry, starry night / You took your life as lovers often do / But I could have told you Vincent / This world was never meant for one / As beautiful as you"
    • hoppdawg, on 10/12/2007, -8/+2Nirvana?
    • RuckusNutz, on 10/12/2007, -3/+10Or White Lion, When the children cry, but Definitely Tears in heaven should be on the list, and Hurt should be #1. IMO
    • PueSi, on 10/12/2007, -1/+2Hmm... it's a little late but i meant "you can't lose"
    • r0b0, on 10/12/2007, -0/+11I find Brick is poorly done on the site. The section which says "water works" should say something like "Can't you see, its not me your dying for" instead of "Now that I have found someone/I'm feeling more alone/Than I ever have before." as I take it as him talking to his unborn baby explaining why the abortion is needed, and I think thats pretty sad or depressing.

      But I guess thats just my opinion...
    • Lynx34, on 10/12/2007, -1/+26At least they got Buckley's "Hallelujah" on there. It makes this list not completely worthless.

      No Piano Man, and nothing from Petty? Bah.

      Also, ditto on Tears and Cats in the Cradle.
    • c1nn46, on 10/12/2007, -0/+7samuel barber has my #1
    • Lane5slacker, on 10/12/2007, -12/+9November Rain - Guns 'N' Roses
    • VelvetoneFusion, on 10/12/2007, -1/+1no "Honey" by Bobby Goldsboro
      Fail.
    • sogracefully, on 10/12/2007, -1/+3"no sunshine" by bill withers
    • DocDEB, on 10/12/2007, -2/+2Who comes up with these lists? Only a few of these are worthy and many big omissions.
      Dante's Prayer by Loreena McKennit; immeasurably sad and uplifting at the same time. iTunes link >
      http://phobos.apple.com/WebObjects/MZStore.woa/wa/viewAlbum?playlistId=67631410&s=143441&i=67631324
    • Bearcharlemagne, on 10/12/2007, -8/+2I'm surprised not to see "The Scientist" by Coldplay on there.
    • tehgoatman, on 10/12/2007, -1/+36mad world?
    • spidoman, on 10/12/2007, -2/+5Brick is about an after-christmas abortion? Well that knowledge is gunna change my listening habits.
    • dn11, on 10/12/2007, -1/+10no nick drake anywhere on the list? any one of his songs would be appropriate.
    • superal1394, on 10/12/2007, -2/+17Tears of Heaven made me cry the first time I listened to it. I was reading about what happened, while listening to it, I just broke down, it was so sad.

      With that, the list is wholly incomplete, especially for missing Last Kiss by Pearl Jam

      That song is seriously my greatest fear.

      "A car was stalled, the engine was dead
      I couldn't stop, so I swerved to the right
      I'll never forget the sound that night
      The screamin' tires, the bustin' glass
      The painful scream that I heard last.

      Oh, where oh where can my baby be?
      The Lord took her away from me
      She's gone to heaven, so I got to be good
      So I can see my baby when I leave this world. "
    • Comatose51, on 10/12/2007, -0/+15Elliot Smith's Miss Misery?
    • ZanCakes, on 10/12/2007, -2/+5I think they got the radio head song wrong - "how to disappear completely" off of Kid A - always leaves me feeling extremely melancholy. Also "Blank Page" by Smashing Pumpkins off of Adore -
      and wtf... Trent Reznor's "Hurt" pwns Johny Cash.
    • skyfire1, on 10/12/2007, -6/+2"Here are 25 little ditties so crushing, they could knock Dick Cheney to his knees."

      More like knock him jerking off to his knees but close enough.
    • XBackstabberX, on 10/12/2007, -2/+2my thoughts exactly
    • soogy, on 10/12/2007, -0/+10Definitely missing Tears in Heaven, though I think Eleanor Rigby should have been number one. There's something really sad about dying alone. I'm really surprised Queen's "The Show Must Go On" didn't make the list; released just six weeks before Freddy Mercury died of AIDS.

      No hip hop songs, though, which is really a bummer.

      "They Reminisce Over You" by Pete Rock and CL Smooth is one of the best hip hop songs ever created; they wrote it after the death of their friend Troy Dixon (aka Trouble T. Roy)

      Nas' "Dance" is depressing, he wrote it after his mother died of cancer, and basically talks about how he would give anything for one more dance with her. And at the end of the song, you hear Nas' father, Olu Dara, playing over the beat with his cornet.

      Jay-Z's "Meet the Parents" and Immortal Technique's "Dance with the Devil" are sad in a twisted kind of way, especially the latter.

      And then there's Tupac's "Keep Ya Head Up", "Baby Don't Cry" and "I Ain't Mad At Cha".
    • Doorfingers, on 10/12/2007, -1/+1Did anyone else notice how that smiths photo looks nothing like the smiths?
    • p_o_b, on 10/12/2007, -0/+3Tears in Heaven is the reason I'm a Clapton fan. When the accident happened I would have thought someone with his history of substance abuse would have crawled into a bottle and never come out alive. Instead he wrote a heartwrenching song that captured his loss and pain. No Tears No Digg.
    • Woody925, on 10/12/2007, -0/+2"You Never Know" by Immortal Technique is another incredibly sad hip hop song.
    • fabeetz, on 10/12/2007, -1/+1Jeff Beck - Cause we've ended as lovers

    • viva162, on 10/12/2007, -1/+5I can't believe Wish You Were Here by Pink Floyd didn't make it. The whole album is about losing Syd Barrett to insanity, that song in particular is very touching.
    • sail191912, on 10/12/2007, -0/+2I find the song 'All By Myself" (no idea who sang it) to be a 'slit-my-wrist' depressing song.
      I was in Japan for a few weeks and that song would play over the company speakers eeeeveryday, during breaktime. And they wonder why people committed suicide.
  • therernospoons, on 10/12/2007, -0/+139Here is the list for those who wish to forgo 25 clicks to read the article:

    25. 'The River' - Bruce Springsteen (1980)
    24. 'Nothing Compares 2 U' - Sinead O'Connor (1990)
    23. 'No Surprises' - Radiohead (1997)
    22. 'A Change Is Gonna Come' - Sam Cooke (1964)
    21. 'Space Oddity' - David Bowie (1969)
    20. 'That's the Way I've Always Heard It Should Be' - Carly Simon (1971)
    19. 'Lost Cause' - Beck (2002)
    18. 'I've Gotta Get a Message to You' - Bee Gees (1968)
    17. 'Back to Black' - Amy Winehouse (2006)
    16. 'Shilo' - Neil Diamond (1968)
    15. 'My Mom' - Chocolate Genius (1998)
    14. 'Anyone Who Had a Heart' - Dionne Warwick (1963)
    13. 'Naked as We Came' - Iron & Wine (2004)
    12. 'In the Wee Small Hours of the Morning' - Frank Sinatra (1954)
    11. 'Brick' - Ben Folds Five (1997)
    10. 'In the Real World' - Roy Orbison (1989)
    9. 'Concrete Angel' - Martina McBride (2001)
    8. 'Dance With My Father' - Luther Vandross (2003)
    7. 'Hallelujah' - Jeff Buckley (1994)
    6. 'He Stopped Loving Her Today' - George Jones (1980)
    5. 'I Know It's Over' - The Smiths (1986)
    4. 'Hurt' - Johnny Cash (2002)
    3. 'Eleanor Rigby' - The Beatles (1966)
    2. 'Gloomy Sunday' - Billie Holiday (1941)
    1. 'Chicken Wire' - Pernice Brothers (1998)

    On the last page there was a link to a story about the #1 song:
    "Meet the Man Behind the Saddest Song"
    http://www.spinner.com/2007/05/04/playing-chicken-with-joe-pernice/
    • utcursch, on 10/12/2007, -2/+12The author needs to be told what "the Whole World" means. The list doesn't even include some of the saddest English language songs. The comments are more insightful: http://www.spinner.com/2007/05/03/the-25-most-exquisitely-sad-songs-in-the-whole-world-no-25/#comments
    • thepompano, on 10/12/2007, -7/+5Beck? Sinead O'Connor? What?

      And as far as choices go... I'd have to say "Heaven Knows I'm Miserable Now" beats out "I Know It's Over" easily, "The Fool On The Hill" > "Eleanor Rigby", and I don't know why they would include a NIN cover song on the list
    • r2pro, on 10/12/2007, -0/+10This is a case where I wish I read the comments before checking out the article.

      Well they got my 25 impressions for their CPM ads.
    • chicken101, on 10/12/2007, -1/+11I'd add "let down" by radiohead. That song is truly sad.
    • thebenchase, on 10/12/2007, -1/+21Where is "Love Will Tear us Apart" by Joy Division? Come on, guys...
    • typo180, on 10/12/2007, -2/+37I'd actually agree with Cash's version of Hurt. It's a pretty damn sad song.
    • theholycow, on 10/12/2007, -2/+1Even sadder song than "Hurt" performed by Johnny Cash: "The Mercy Seat".
    • pifko87, on 10/12/2007, -7/+4"No Suprises" by Radiohead?

      I personally find that song uplifting, but whatever...
    • numb, on 10/12/2007, -1/+23The Kermit the Frog version of Hurt is the saddest video I've seen.

      http://www.sadkermit.com/video.html
    • antitab, on 10/12/2007, -3/+38No "Mad World" Gary Jules version??
    • ihavebeenseen, on 10/12/2007, -2/+3if there are no Fado songs then this is no sad song list. That genre is built around the sad song.

      http://en.wikipedia.org/wiki/Fado

      Also put a Cure song on there
    • TheKricket, on 10/12/2007, -3/+10interesting beck made the list - but id switch it to "guess i'm doin fine" - meh, to each his own

      i don't think one sad song is necessarily sad to everyone who listens to it - its more of the "oh man, that song is totally about me" moment that really gets you

      although tears in heaven is just sad across the board

      one more thing - im a HUGE nine inch nails fan - johnny's version is more heartfelt - period

      heres what trent had to say about the first time he heard johnny's version:

      "We were in the studio, getting ready to work -- and I popped it in," Reznor says. "By the end I was really on the verge of tears. I'm working with Zach de la Rocha, and I told him to take a look. At the end of it, there was just dead silence. There was, like, this moist clearing of our throats and then, 'Uh, OK, let's get some coffee.''
      - CMT 2003 Video Music Awards Tribute to Johnny Cash - honored as the "Greatest Man in Country Music"
    • orientis, on 10/12/2007, -2/+1No surprises... It's a requiem for people who, "when I am king, will be first against the wall". It's not about Yorke's personal feelings. ffs. Apparently all you need to make the list is a downbeat.
    • dn11, on 10/12/2007, -1/+5this is a very poor list. where is NICK DRAKE - he is the king of melancholy.
    • FRANKeB, on 10/12/2007, -4/+2Who the ***** are the Pernice Brothers and which guy from that band is related to the ***** that wrote this article?
    • strcmp, on 10/12/2007, -0/+1See also http://en.wikipedia.org/wiki/Robert_Johnson_%28musician%29#Songs
    • Ridikul, on 10/12/2007, -0/+1No Agalloch?
    • Rikka, on 10/12/2007, -2/+1What a disappointing list; Some songs i think should have been put in there to replace the other songs:

      Avril 14th - Aphex Twin
      Hoppipolla - Sigur Ros
      Breathe - Telepopmusik
      Something about us - Daft Punk
      Let Down - Radiohead

      I could actually go on, but then I'd just be ranting. Cheesy list, but that's what it's supposed to be, right?
    • lunarworks, on 10/12/2007, -0/+1"No Surprises" by Radiohead never really affected me.

      "Fake Plastic Trees"... now THAT is a song that has a strong power to it. Nothing terribly tragic about it, just a powerfully melancholy song. Thom Yorke actually broke into tears after recording it. It tugs at me, too, when I listen to it.
  • fhernand, on 10/12/2007, -2/+37the saddest songs ever are the ones i sing in the shower
    • fhernand, on 10/12/2007, -0/+20ok, blatant comment abuse, but it's my comment, so its ok... right?

      seriously now, the one song in futuramas episode with fry's dog is also kind of sad. Which makes the whole scene even sadder, if that's even possible. I think its called "I will wait for you", but no idea who it is originally from.

      http://www.youtube.com/watch?v=akf-H0OVpLA
    • duckrank, on 10/12/2007, -0/+7http://xkcd.com/c233.html
      (Hover over the comic)
    • soogy, on 10/12/2007, -2/+2That's the only episode of Futurama I don't watch anymore. It's ***** depressing as hell.
    • kingfelix, on 10/12/2007, -0/+4fhernand,

      you are right, that song is one of the best. the original is the main theme from a 1964 french film called "les parapluies de cherbourg" (the umbrellas of cherbourg), my favorite movie of all time. the english version of that song is called "i will wait for you." this version is a bit cheesy, but the melody is still fantastic.

      i would also add to these comments an unreleased elliott smith song called "true love."
      most beautiful sad song i've ever heard.
    • tech42er, on 10/12/2007, -0/+2Oh man, that's one of the reasons that was such a good show. I never fail to shed a tear during that episode :'(
    • Ridikul, on 10/12/2007, -0/+1http://www.lyricsdepot.com/andy-williams/i-will-wait-for-you.html
    • Steelfox, on 10/12/2007, -0/+1The song in Futurama is by Connie Francis - I will wait for you. Sort of hard to find but you can find it on bittorrent or p2p.
  • NCRider, on 10/12/2007, -11/+4Need to include "What Sarah Said" by Death Cab for Cutie.


  • domdunc, on 10/12/2007, -0/+12Wise Up - Aimee Mann
    • BlackSheepx, on 10/12/2007, -0/+2Ugh, yes..everybody should watch the movie Magnolia, if for anything the ending scene with that song in it. The movie will have you bawling.

      And if I can add my own to the list, "At the Hop" by Devendra Banhart
  • JrGhoull, on 10/12/2007, -15/+1the calling-if i could
  • russizm, on 10/12/2007, -8/+3Kind of weird they chose the cover for #4 instead of the original. oh well.
    • Koopa, on 10/12/2007, -4/+25Johnny Cash does way more justice to that song than NIN ever could....I think NIN even admitted that somewhere.
    • patik, on 10/12/2007, -6/+4I thought there was a lot of hype around that cover since it was the first song in a while from Johnny Cash, then he died, then the movie came out, etc. I still don't think it's anything too great, though I like the original.
    • wvannus, on 10/12/2007, -0/+15"I pop the video in, and wow… Tears welling, silence, goose-bumps… Wow. 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."
      -Trent

      Reznor still occasionally refers to "Hurt" as "a song that isn't mine anymore."
    • HunterTV, on 10/12/2007, -1/+16There are times when a cover trumps the original, and "Hurt" by Cash is one of those times. You have to give props to Reznor for admitting it. I think it's power comes from the fact that Cash was on the other end of what Reznor was writing about while he was still young.

      I nominate "Cat's in the Cradle" though. I've listened to a lot of music that some would call depressing without blinking, but I seriously have to change the radio station when that song comes on. It's paradoxically excellent but unlistenable for me.
  • Vortical, on 10/12/2007, -8/+3Pearl Jam - Black ..........should be No. 1 and it's not even on there.
  • phenom2k7, on 10/12/2007, -0/+1025 pages, are they taking the piss. Thanks for posting the info here. Plus it's likely the site will go down before you reach the end.

    What were they thinking of, nobs.
  • marcusb, on 10/12/2007, -1/+10No Tom Waits? No good..
    • TDot1980, on 10/12/2007, -0/+2"Christmas Card From A Hooker in Minneapolis" is a good candidate. But then again, pretty much all his songs make me want to /wrists.
    • VelvetoneFusion, on 10/12/2007, -0/+2That pathetic horn solo at the end of Burma Shave hits it every time.
  • johnroa11, on 10/12/2007, -5/+0I am with Vortical 100%. This list is BS without PJ - Black.
  • oonix, on 10/12/2007, -3/+10what happened to all of Sarah McLachlan's songs..... :(
    • SR388, on 10/12/2007, -2/+1well, she did cover Gloomy Sunday, so, that kind of counts.. but not really. But her rendition is pretty decent.
    • Fogdelune, on 10/12/2007, -0/+1Yes, I would say "Angel" or "World on Fire" would have been good. Too many love songs on there, not enough about the other aspects of life.
  • RequiaNocturne, on 10/12/2007, -2/+5"Christmas Shoes," anyone?
    • bigstinky, on 10/12/2007, -1/+12Speaking of Christmas shoes, When I was a kid, we were so poor that my Mom had to cut holes in my pockets so I'd have something to play with on Christmas morning.

      Christmas shoes makes me want to kill myself.
    • zybch, on 10/12/2007, -2/+1ANY christmas song for that matter!
    • fantasticjon, on 10/12/2007, -1/+1That "christmas shoes" song makes me ball like a little baby every time I hear it.
  • cryptomystic, on 10/12/2007, -22/+2It's funny how the whole "World" only consists of the U.K and U.S.
    Buried as Inaccurate.
    • mikedmoon, on 10/12/2007, -2/+9Ya! This english language website should put more non-English music selections on its list.
    • mattyxo, on 10/12/2007, -0/+5Canada too... ***** wait. We don't speak English.
  • Laytonx, on 10/12/2007, -1/+17The Smiths could have filled this list on there own.
    • VelvetoneFusion, on 10/12/2007, -1/+3I never thought Smiths songs to be that sad, as the lyrics are almost always happy bouncy music. The list is of depressing songs, not depressing lyrics.
    • VelvetoneFusion, on 10/12/2007, -0/+2set to happy bouncy music, I mean.
    • sogracefully, on 10/12/2007, -0/+2the smiths could fill up all 25 slots in a "most melodramatic" songs list...
    • Namco, on 10/12/2007, -0/+1I Know It's Over nails it. Most people who would pick a sad Smith's song would pick How Soon Is Now, but a fan would know it's I Know It's Over... or maybe That Joke Isn't Funny Anymore.... or maybe Asleep.
    • Namco, on 10/12/2007, -0/+1Isn't every sad song melodramatic by definition?
    • bixel, on 10/11/2007, -0/+0"The Smiths could have filled this list on their own." That was my 1st thought or at least the Smiths could have taken 5 slots, and then Portishead for at least 1, Tom Waits for maybe most of the other part of the list, and possibly 1 from Divine Comedy. I am so glad at least Billie Holiday was on there, though there are many more from that time period that is so sad.

      Thank god there was no R.E.M. Ben Folds Five - nothing they can do will make me listen.
    • Doorfingers, on 01/24/2008, -0/+1Is the picture of the smiths actually a picture of the smiths at all?
  • zoto, on 10/12/2007, -1/+26no "mad world"?
    • soupnrc, on 10/12/2007, -0/+10Agreed. Also, I would like to ask why "Nobody Home" by Pink Floyd isn't on the list. That song is WAY sad.
  • Abjure, on 10/12/2007, -6/+1beat me to it
  • manfatallyslain, on 10/12/2007, -7/+2No Adams Song? Its about a guy they knew who comitted suicide.
    • crunkaholic, on 10/12/2007, -8/+3blink182 is sad. while their songs... not so much.
  • XandraX, on 10/12/2007, -0/+11Surely Elliott Smith could have been included somewhere...I Didn't Understand is soooo sad.
    • tehkain, on 10/12/2007, -0/+2Yes I agree. I also found hurt(the original by Trent) to be far sadder then Johnny's. Everyone gets old and dies. Its far more accepted then what Trent was singing about and easier to cope with in the end.
    • Namco, on 10/12/2007, -1/+1I love hurt, but it's not exactly sad, but more an expression of pain mixed with depression.
  • DeFex, on 10/12/2007, -3/+18Very nice not to see any emo crap in there!
  • wachter1, on 10/12/2007, -0/+2Harry Chapin should have at least 5 songs in the top 25. That guys songs were so sad they were downright hilarious.
  • fordistumley, on 10/12/2007, -0/+4It's bad enough to omit "High Time" or "Box of Rain" by the Grateful Dead, but how can anyone compile a list of sad songs without a single tune by Hank Williams, Merle Haggard, Bob Dylan, or Neil Young?
    • mwolfzorn, on 10/12/2007, -0/+7At least they got Springsteen & Cash on the list...
    • bobcrotch, on 10/12/2007, -0/+1Did you honestly expect anything less from the * in The Whole World list?
  • gerrylazlo, on 10/12/2007, -5/+2The Cash version is certainly one of the saddest _videos_ I've ever seen, but I dont' think the song by itself is.
  • hzrds, on 10/12/2007, -1/+8I'm going to have to respectfully disagree with this list.
  • gostars, on 10/12/2007, -8/+2Most lame song list ever.
  • lothar250, on 10/12/2007, -0/+2the lyrics and meanings of the songs are definitely sad, but the songs themselves dont really sound sad
  • subxero37, on 10/12/2007, -8/+2Gah, they're missing My Immortal by Evanescence. Yeah, I'm a man, and I listen to it. Great song.
  • DaffyDuck, on 10/12/2007, -0/+5Well, it looks like we all have songs to add to this list. I would add "From the edge of the deep green sea" by The Cure to this list. Very sad song.
    • WITFITS, on 10/12/2007, -1/+4Just about anything from The Cure could have made the list.
  • Durinthal, on 10/12/2007, -4/+1I'll agree that Gloomy Sunday should be way up there, but Eleanor Rigby? The music itself doesn't quite set up the mood, though the lyrics do somewhat fit.
  • HappyMax, on 10/12/2007, -0/+0Patches?
    • godcomplex, on 10/12/2007, -0/+3we don't need no stinking patches!
  • boredsam, on 10/12/2007, -1/+1Pretty much any entire Portishead album could fit this list. Most of The Bends as well. Unkle's 'Rabbit in Your Headlights'.
  • trubbleshute, on 10/12/2007, -0/+7Too much love will kill you. By Queen -- google the lyrics.
  • Hoss, on 10/12/2007, -4/+5"Last Kiss" cover by Pearl Jam - my #1
  • Urusai, on 10/12/2007, -9/+5U2 writes the saddest songs. It makes me depressed that people actually buy their albums.
    • camilos, on 10/12/2007, -6/+4"It makes me depressed that people actually buy their albums."

      What are you talking about? Beautiful Day, Vertigo, Mysterious ways, Desire etc
      Not all their songs are sad, and I'm pretty sure most are about hope.


  • santiago1, on 10/12/2007, -1/+8
    Terry Jack's "Seasons in the Sun"?
    I mean come on, yeah, it sucked, but the guy was dying and saying goodbye to everyone!
    Oh, wait, most of you are probably too young to remember that song....




  • camilos, on 10/12/2007, -1/+8Pretty cool list. Although alot of the songs I didn't know.

    They also have the "worst lyrics list"
    50 Cent's '21 Questions : "I love you like A fat kid loves cake"

    No question about it, the man is a poet.
  • moojj, on 10/12/2007, -4/+4I never knew 'Brick' was about an abortion. I never really listened to the lyrics, but knowing this makes it so sad.
  • tizz66, on 10/12/2007, -3/+18It's not strictly sad in terms of being about someone dying etc., but John Lennon - Imagine is a tearjerker because it's positive. I guess it's indirectly sad because it explains why the world sucks.

    Another one is Everybody Hurts by REM.
    • dezmo, on 10/12/2007, -1/+2also, jelouse guy by lennon, imho one of the best songs ever writen
  • bigdt87, on 10/12/2007, -2/+1They need to check out some slowcore/sadcore and make a new list. Codeine FTW...
  • Trenchbroom, on 10/12/2007, -3/+1Soon as I saw this list I thought: "This is gonna be some top 40 'sad song' BS that will ignore the more obscure but very compelling artists and their songs". And then they put Iron & Wine on the list and the Pernice Brothers grab the #1 spot.

    In short: nice work!
  • stauken, on 10/12/2007, -15/+3Buried for saying 25 sad songs from the whole world with nothing but US songs in the list -- lame. We're not the only country who knows sadness.
    • AllnightChemist, on 10/12/2007, -0/+11But you're the only Digger who doesn't know that Bowie and The Smiths are from the UK.
    • AllnightChemist, on 10/12/2007, -7/+2WTF. Is Digg's comment system broken? Digg me down, but I swear I was responding to a comment waaay down there````V
    • stauken, on 10/12/2007, -6/+3Ok, my bad. So, two countries represents the world how?
    • aaronm67, on 10/12/2007, -1/+5It's an English website. Most popular English music is from the US or England.

      Also, most people don't want to read a list about a bunch of songs they've never heard. And, being an English website, most people reading it have heard of a good portion of those artists, and heard a good portion of those songs.
  • extratired, on 10/12/2007, -1/+4useless list, music is way to personal to determine a list of saddest songs.

    I agree with #1, tears in heaven was the first song I thought of as well. and then maybe REM's everybody hurts. also nice to see jeff buckley in the list, eventhough halleluja isn't his saddest song to me.
  • herrshuster, on 10/12/2007, -14/+2
    hurt is by nine inch nails
    • herrshuster, on 10/21/2007, -14/+1why am i being dugg down? it's true and the credit needs to be given
    • fantasticjon, on 10/12/2007, -0/+9we know.
    • allyant, on 10/12/2007, -7/+5Cash brought the song alive, even NIN said that it's no longer recognised as there song. But we know that it was written by NIN but the JC version is MUCH better than some emo version.
    • alf86, on 10/12/2007, -0/+3I don't think he means the song itself so much as the song as performed by...
    • Stunn, on 10/11/2007, -0/+1The site even mentioned that the Johnny Cash version was a Nine Inch Nails cover. In the big scheme of things, it really doesn't matter. It doesn't need to be pointed out everywhere.

      If you read the comments on any version of "Hurt" on YouTube, there is a barrage of people who truly believe that Cash wrote the song. Go bug them.

      I first started listening to Nine Inch Nails because of Cash's cover. I ended up liking the Nine Inch Nails version more, but I feel Cash's version is a lot more powerful. He sings the song with such emotion it becomes depressing. I try to listen to music now thats uplifting for me.
  • exentropic, on 10/12/2007, -0/+13Strange Fruit sung by Billie Holiday is the saddest song I've ever heard. Ever.
    • h0ly, on 10/12/2007, -2/+11Strange Fruit
      Billie Holiday

      Southern trees bear strange fruit
      Blood on the leaves
      Blood at the root
      Black bodies swinging in the southern breeze
      Strange fruit hanging from the poplar trees
      Pastoral scene of the gallant south
      The bulging eyes and the twisted mouth
      The scent of magnolia sweet and fresh
      Then the sudden smell of burning flesh
      Here is a fruit for the crows to pluck
      for the rain to gather
      for the wind to suck
      for the sun to rot
      for the tree to drop
      Here is a strange and bitter crop

      http://youtube.com/watch?v=h4ZyuULy9zs
    • varble, on 10/12/2007, -1/+0Thank you! My thoughts exactly.
  • bergetun, on 10/12/2007, -0/+7Where is the torrent ?
  • phenom2k7, on 10/12/2007, -3/+1Crap list.
  • tritiumpie, on 10/12/2007, -1/+1Notably missing from the list:

    "He Ain't Heavy, He's My Brother" by Rufus Wainwright
    • ayeroxor, on 10/12/2007, -1/+3That's not "by" (originally authored by) Rufus.
    • LCmidas, on 10/12/2007, -0/+1Read the list and comments, no mention of Flipsyde's "Happy Birthday." I've been accused of being a cold lesbian bitch before, but that song always makes me want to hug my pillow and cry all over myself...
  • mikedmoon, on 10/12/2007, -1/+11Gary Jules singing Mad World on the Donnie Darko soundtrack.
  • tizz66, on 10/12/2007, -0/+2Another really sad song: Wires by Athlete. Most of you probably won't have heard of them since they're really only popular in the UK right now, but as far as songs about a baby brother in intensive care goes, that's a tearjerker.
  • xcbxcb, on 10/12/2007, -3/+2Pogues - Pair of Brown Eyes

    Buried as bollocks.
    • coloneltcb, on 10/12/2007, -0/+2"The Band Played Waltzing Matilda" is even more depressing than "A Pair of Brown Eyes"

      This list needs "For the Good Times" by Kris Kristofferson.
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