[ordinaRynne]

Mine's
Cinderella by Steven Curtis Chapman.
This man lost his youngest daughter hours before his eldest daughter's engagement party,
days before his son's graduation party.
She got ran over by Chapman's 16 year old son accidentally.

How sad.
I wouldn't know what to do if I were him.

[dolcedor.]

Whiskey Lullaby by Brad Paisley

It's about a guy that was so heartbroken when his gf cheated on him that he killed himself. Later on, the girl feels so guilty she does the same. In the MV, he forgives her though, and they're reunited in death.

[lovefool]

Donny Hathaway- A song for you
(the original is by leon russell)
i don't know if it'll compare to the two songs above me but everytime i listen to it...it just makes me think of losing someone over your own mistakes..

i also like the version by usher..well its not really a cover song but he sang it love once and it was beauitful (even though he paused for a few seconds and went off pitch in one high note..but he almost teared up!)

usher- song for you performance

[royalpirate.]

I Don't Love You by My Chemical Romance

♥ I love that song.

[Raix]

wth. ENGLISH HAHAAH
hmm...
When You Were My Girl by Anthony Callea always made me sad for some reason. It's just about regret after breaking up with someone but I don't know. It's sweet.

Nineteen Stars by Meg & Dia is heartbreaking in the sense of what the person it's about is going through. It was written to be hopeful but the overall story's sad.

[Lunea]

The Man Who Can't Be Moved - The Script

Listening to it on repeat during a fan fic = buckets of tears. And I'm not sure if they were due to the fan fic either.

[chocopocky]

Alyssa Lies by Jason Michael Carroll

Concrete Angel by Martina McBride

Both are about child abuse and definitely very depressing

[trashstar]

Wild Horses by the Sundays (original by Rolling Stones)
the lyrics themselves don't sound too sad, but the way she sings it is great

[mizer_unmei]

The Smith's I Know It's Over is the only song in recent memory that really touched me when I finally listened to the lyrics.

Their Meat is Murder live gives me chills too. After you get over the first shock of the studio recording and it's lyrics, his voice in the lives versions are just too haunting.

[Iridescence]

Tears in Heaven by Eric Clapton.

He wrote it for his son, whose death resulted from falling out of a building. It's quite tragic and it always makes me cry.

[Starry.nights]

Unbreak My Heart - Toni Braxton

this song gives me chills....

[super piggy]

all 4 one - not ready for goodbye.
deepside - dont tell me its over
well okay, its not THAT heartbreaking but when you're in that position, its hella heartbreaking.

[xWiReDx]

Third Eye Blind - The Background
Oasis - Roll It Over
Ocean Colour Scene - Robin Hood
Frank Sinatra - I'm A Fool To Want You

I'm sure there are more depressing songs...but these hurt me the most. I think about what could have been, what should've been...how things are. How its all my fault.

[Allison]

Confessions (Of a Broken Heart) - Lindsay Lohan.
The lyrics to the song make me tear up.

There's a lot of other songs, but that one was the first one that came to mind.

[chibichi07]

I Miss You Like Crazy- The Moffats (don't laugh, it made me tear up ='()

[Magena Angel]

Just so you know by jessie mccarney

[catsinheat]

The Smith's I Know It's Over is the only song in recent memory that really touched me when I finally listened to the lyrics.

Their Meat is Murder live gives me chills too. After you get over the first shock of the studio recording and it's lyrics, his voice in the lives versions are just too haunting.

seconded. 'asleep' is also quite sad. whether it is or not, i always think it's about suicide.

[c'erine]

for me, it's definitely
dance with my father - luther vandross
it makes me cry every time i listen to it

[Lie]

Mew's She Came Home For Christmas.

[JAMIEE]

daddy's little girl -frankie j