What is the saddest song you've ever heard?  

I have heard many a sad song in my time, but one that lately seems near me again is by one of my favourite singers of all time, Bruce Springsteen- ''Streets of Philadelphia''

http://www.youtube.com/watch?v=ODYZZgHQKPs

A movie was made with this song in 1993, called "Philadelphia", based on a true story, and starred Tom Hanks, Denzel Washington, Mary Steenbergen, Antonio Banderes etc and really told the horrendous agony of homosexuals dying from AIDS.. Very compelling it was and the song that Bruce sang soo described the pain and set the tone with the special sadness in the cords of the music.

It always comes back to me with the same kind of unspoken sadness.. rather like man's inhumanity to man.. a shared shame in the city of 'brotherly love'' and outside it, that not all man are are loved and respected.
Heartbreaking and sad.. for ME, anyway.

Yes, I have heard of Gloomy Sunday. It is indeed very sad...

A few songs that made me cry where "When You're Gone" by Avril Lavigne, I cry every time I listen to that song because I feel an empty hole in my heart because someone close to me is gone.

Another song is "Winter" by Tori Amos. The lyrics are very meaningful; it is about her and her father. One part in the lyrics say the "white horses are still in bed"; and then at the end it says "all white horses have gone ahead" meaning her father has died.

J Entercom - kiss, i think is a song that really makes you cry, does matter if is not an english song just watch the video and you will be very sad. i love that son and i cry every time when i listen

The saddest song that I have ever heard was sung by the singer/actress Bett Middler. She sang both the song "The Rose" & starred in the movie as well. The words to this song are so sad. Whenever I hear this song I find myself almost near tears. It's doesn't help that this was my Mom's favorite song. Whenever I hear it I think of her.

There is a song that always makes me want to cry when I hear it. It came out shortly after the 9/11 attack and it just has a really emotional connotation to me. I believe the song is by Toby Keith and I believe the name of it is "I'm Already There." It's a song about a man who is away on business or something and he calls his family and talks to his daughter and his wife and his daughter asks him when he is coming home and he tells her that he is already there. Of course he means his heart is there and it just tugs at my heart strings every time I hear it.

"Concrete Angel" by Martina McBride. It's a song about a little girl who is abused by her father, and is implied to have been beaten to death by him. The title refers to a statue that was built in the girls' honor (I'm not sure whether it exists or not). Gosh, I feel like crying just thinking about it...

"Fast Car" by Tracey Chapman is another sad song. It's about a woman and her partner who live in a homeless shelter. The woman reminisces about her tragic family life and wonders what she should do with her life next.

a very sad song for me is "dance with my father" by luther vandross. whenever i hear this song, it makes me think about life and death - how a family can take a death of its member. i've always wondered how i would take it - death of someone close to me; i haven't experienced it yet. the thought of it scares me. most of the time, i pray to God to take me instead of a loved one because i'm afraid i could not bear the pain.

well there's 2 actually, one is tears in heaven (eric clapton) and the other is don't give up (peter gabriel and kate bush) both songs make me feel sad because each song is a reminder of a certain part of my life that wasn't so good, so i tend not to listen to them because they do make me sad.

Hi, Anima Welcome to Mylot!
She's Out of My Life by Michael Jackson never fails to twist my heart a little. When I googled it, I found out that it was written by Tom Bahler after Karen Carpenter broke up with him.
American Pie by Don McLean also sounds heart-wrenching for me.
Have a nice day!

i've always liked "Honey" by Bobby Goldsboro. it's an old song a man retelling his love for his wife. it's special to me because it reminds me of my parents. they love the song and the song fits them...