Saddest song you ever heard?

Reaper

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A SAD SAD SON
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http://www.youtube.com/watch?v=nrD9Od1wI8Y
http://www.youtube.com/watch?v=nrD9Od1wI8Y
http://www.youtube.com/watch?v=nrD9Od1wI8Y
http://www.youtube.com/watch?v=nrD9Od1wI8Y
 

Domination

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Zeppelin Blues ftw!!!

I couldn't care less about the original version's sharp and irritating vocals. But I guess it sounds as sad too.

This song is just great.

Edit:

Just remembered this song

 

FAST6191

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Trouble with this is if it is too "sad" it rapidly becomes "boring" and I pay no attention.

Tom Waits was a near certainty here, to pick one would be hard so I am going with Another Man's Vine as a cop out of sorts:
 

R2DJ

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+1 to Madworld. The Kiwi one got into me...

Brian McKnight - Back at One

Was very lucky. The first time I got cable (9 years old) this is the first music video I saw the first time I tuned to MTV...in cable! I love this song. I miss the old days when 90% of the MVs showed in MTV were worth listening to.


I Will Be Here - Gary Valenciano

This was played in my granddad's funeral. Very touching. The singer is Filipino and he is known for making the best love songs and songs in general...IMO at least. I'm a fan of his.


Usher - Separated

Usher - Can You Help Me

These two have the highest play count in my iTunes library
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Why? They're just awesome...I love Usher and this kinda brings back childhood memories. God bless my uncle who is a very reliable source of the best RnB music
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Notable mention:
One Last Cry - Brian McKnight
All My Life - KCi and JoJo
 

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    K3Nv2 @ K3Nv2: https://youtu.be/NAum8AcoiWs?si=LfXd2oXysAy_HjDU he was in a shitty situation +1