'Ex-Factor,' Lauryn Hill
"Ex-Factor" is like a modern-day version of Roberta Flack's classic "Killing Me Softly." Some people think the pain and confusion in Lauryn's voice on this song foreshadowed the emotional breakdown that she went through a few years later.
'Can't Let Go,' Anthony Hamilton
This song is painful in two ways: one, it's sad that in the song, Anthony has lost the woman that he obviously loves so much. But it's also sad in the way that it epitomizes how some people can't or won't allow themselves to get over the grief and move on.
'Irreplaceable,' Beyonce
"To the left, to the left." The funny thing about this women's anthem about kicking a man to the curb is that the lyrics were actually written by a guy: Ne-Yo.
'Everybody Knows,' John Legend
John Legend has never sounded as sad as he does on this break-up tune about a man who's still hurting emotionally after his old flame gets a new man.
Sample lyric: "I still can't believe you found someone new, but I wish you the best, I guess."
'Un-Break My Heart,' Toni Braxton
Toni Braxton's finest moment as a singer came when she managed to reach the lowest of lows emotionally. Damn, this song is so sad it can make people cry for hours at a time.
'So Sick,' Ne-Yo
It doesn't get more real - or sad - than not changing your answering machine message so that you can still hear the voice of the person who broke your heart.
'Not Gon' Cry,' Mary J. Blige
Believe it or not, this song was also written by a man: singer-songwriter Babyface. A taste of the lyrics:
"While all the time that I was loving you, You were busy loving yourself, I would stop breathing if you told me to, Now you're busy loving someone else, Eleven years out of my life, Besides the kids I have nothing to show, Wasted my years a fool of a wife, I shoulda left your ass a long time ago."
'I Need You,' Mayer Hawthorne
On this doo wop-style song, Mayer sorrowfully laments how he let his woman get away, and how much he needs her back in his life.
Key lyric: "When I saw you last night, it brought back memories to life/Of how we used to love one another, so sad we didn't go any further."
'How It Was Supposed to Be,' Ryan Leslie feat. Jadakiss
This mid-tempo break-up song is about a man who's dumped by his girl, then wonders what their life together would have been like.
Sample lyrics: "Now when I think back to the days that you were mine, oh how I wish I could flip the switch to turn back the hands of time/You were the one that made me real, Now that you're gone tell me, what in the world am I supposed to feel?"
'Used to Be My Girl,' Brian McKnight
Key lyric: "Go 'head playboy do your thing, don't be mad when she calls my name."
'How Can You Mend a Broken Heart,' Al Green
The title says it all; this is the kind of song that you want to listen to while drowning your sorrows in a bottle of scotch. Painful though the song is, it's also arguably the most shining moment in Reverend Al's long, glorious career. The Bee Gees may have done the song first, but Al did it best.
'Tyrone,' Erykah Badu
Maybe the coldest, funniest dismissals ever of a triflin' man:
"I'm gettin' tired of your sh*t
You dont never buy me nothin'
See everytime you come around
You got to bring Jim, James, Paul & Tyrone."