7. OutKast, "Roses" An album called The Love Below was almost guaranteed to explore the darker side of these things as well, and our generation's Prince put forth his own "When Doves Cry" with this heartbroken hit.
6. Kanye West, "See You In My Nightmares" Almost any track from Kanye West's last three albums could make this list, but this one is perhaps his best kiss-off, complete with an utterly ridiculous Lil Wayne verse that still stands as one of the best he's ever laid to wax.
5. Ghostface Killah, "Back Like That" With a Jay Z quote and sample, even Ghost got emotional on 2006's Fishscale, complete with Ne-Yo on the chorus. Of course, he still talks about cutting off ring fingers in the lyrics. He took a much more humorous approach to these things a few years later with Fabolous on the excellent "Guest House."
4. Why?, "Good Friday"
Okay, these other dudes got emotional, but none of them can even approach the raw honesty of Yoni Wolf's epic exploration of the broken remains of a man after a breakup in Why?'s "Good Friday."
List continues on the next page.