[jonyoo]

T-Square - Pain in my Heart
Japanese fusion jazz with sax on the leads. This song just melts my soul lol.

 

[Nuwidol]

I'm gonna suggest some slightly weirder tracks here. I see a lot of people suggesting mainstream artists so I'm going a different direction here.
 
yosei - blue parrot. I tried to find a link to it but theres not much out there. Spotify link if you have it
 
Manchester Orchestra - Sleeper 1972
 

 
Now this next one is not what anyone will be expecting a sad song to sound like but if you do click the link then just listen to the lyrics. If you also somehow found you enjoyed the grating harsh vocal tones & depressing story then give King Park a listen too. Its probably their more famous track but I prefer this one. Be warned though its very dark & deep...
 
La Dispute - Edward Benz 27 Times
 

 
Actually, here's King Park too
 

 

[z7nz]

 

 

[jakol]

Blind Faith : Had to Cry Today, Can't Find My Way Home
Wailin' Jennys : Prairie Town
Bill Withers : Ain`t No Sunshine

 

[MedicalPartisan]

Forever and Always, Parachute. If you have three minutes, read these lyrics while listening. It's a really, really sad story, IMO. 
 
 

 

[jimr101]

Johnny Cash Hurt

 

[SlimShadyMJ]

Stranger in Moscow by Michael Jackson is one of my favourite sad songs. In fact, one of my favourite songs of all time. It's just so haunting and beautiful. You can feel the torment and sadness in his voice.
EDIT: heres the video

 

[SlimShadyMJ]

  Forever and Always, Parachute. If you have three minutes, read these lyrics while listening. It's a really, really sad story, IMO. 
 
 

that was so good. Some onion ninja decided to show up near the end though. Damn those onion ninjas

 

[gibbro]

I CRI EVERYTIEM
 

 

[whoever]

Le fil du temps


From poni hoax: album: poni hoax

 

[Kernmac]

I'm not a country fan, but it is hard to listen to this song and focus on the lyrics and not get emotional, particularly if you are heading toward your twilight years with your life partner.
Alan Jackson -Remember When
 
 

 

[tattoou2]

"Dress Rehearsal Rag" by Leonard Cohen
 
"River" by Joni Mitchell

 

[epicFAIL]

Serious One from me :
 
http://www.youtube.com/watch?v=DChHEf0lpEE

 

[ralphp@optonline]

Great thread with lots of really good sad songs listed. Glad that someone bumped it up from the archives.
 
Here are four more selections capable of making a grown man cry.
 
Holly Cole - Take Me Home (written by the great Tom Waits, from her CD "Temptation" which features all Tom Waits' songs)

 
Ellen McIlwaine - Say A Single Word (from her album "Everybody Needs It")
Sorry no video.
 
K.D. Lang - Nowhere To Stand (from her album "Absolute Torch and Twang")

 
Richard Thompson - 1952 Vincent Black Lightning (from his album "Rumor and Sigh")

 

[wuwhere]

Ravel's Pavane Pour Une Infante DeFunte
 

 
From the same album.