Bye Bye- Mariah Carey
Storm is Over- R Kelly
(^^saddest songs They makes me cry everytime^^)
Since Youve Been Gone- Day 26
Poetry- Danity Kane
The Way that I love you- Ashanti
(^^Good breakup songs^^)

Break up songs always depend upon whether you are the dumper or the dumpee. For the dumper, I like:

"You're Moving Out Today" - Carole Bayer-Sager
"Life Goes On" - LeAnn Rimes
"Sober" - Jennifer Paige
"You Sh!t Me To Tears" - The Tenants
"Don't Shed A Tear" - Paul Carrack

If you are the one getting dumped, it's a very different kettle of fish.

"Crucify" - Tori Amos rings true for me, as does "The Flame" - Cheap Trick (shows my age, huh?).

There are so many I've always liked, but I haven't been on either side of the dumped line for a little while now.

Two of the saddest country artist songs:

"Where've You Been" by Kathy Mattea (If this song doesn't make you cry, nothing will!)

"He Stopped Lovin' Her Today" by George Jones (This is considered by many to be the greatest 'country' song ever written. It's sad because death is the reason he stopped loving her today.)

"Must have been love" Roxette

One of the saddest pop ballads ever is Rick Nelson's "Lonesome Town" and one of the prettiest.

tjoeb}:>

I completely agree with those that nominated Concrete Angel by Martina McBride. That's a beautiful song.

Others on my list include:
Taylor Swift - Teardrops On My Guitar
Miley Cyrus - Goodbye
Rascal Flatts - What Hurts The Most

but the saddest by far, for me anyway

Brad Paisley & Alison Krauss - Whiskey Lullaby. I blubber like a baby every time!