For all the talk about hip-hop and Auto-Tune, it’s worth
remembering that sometimes rappers sing without robotic pitch correction. And
when they do, hilarity ensues! Here are six moments we wouldn’t dare correct
with technology.
1. Biz Markie, “Just A Friend”—The quintessential off-key
hip-hop jam. It’s such an immortal example of
unselfconscious warbling that it recently appeared in a beer commercial, some
20 years after its initial release.
2. Soulja Boy, “Turn My Swag On”—Kudos to Soulja Boy for being so unrepentantly bad, taunting the haters in a song that pretty much symbolizes why they hate in the first place. Ride that Segway, man. Just ride it.
3. 50 cent, “Where You Are”—Apparently recorded just after Michael Jackson’s death, this cut provides a rare opportunity to hear 50 rap over an MJ sample, then sing along with it! Although he sounds at one point like he’s been scalded by burning water—ah-aaaaaa!—the song is weirdly sweet, as though a fearsome gangsta rapper is singing into his hairbrush.
4. Kanye West, “We Don’t Care”—One of the many things Kanye
apparently doesn’t care about is the sound of his singing voice. Of course,
this was just the first song on his first album. 808s proved that he actually does care. And some of us kind of love it when he sings,
Auto-Tune or not. But we didn’t know he meant “kids sing” literally!
5. Jay-Z, “Wonderwall”—Mr. “I Hate Auto-Tune” could maybe use just a touch, no?
6. House of Pain, “Danny Boy, Danny Boy”—First comes the rapping. Then, the "singing." Fans of the traditional Irish ballad, listen at your own risk.

I up your Biz Markie tune slap down by replacing it with the seminal "Toilet Stool Rap." It's as off key as "Just a Friend" and is perhaps the best rap video ever.
christopher wallace... sean combs assisting with the background vocals... playa hater... off-key vocalizing at its worst...
How in the name of all that is holy (get it?) could forget our favorite rapper turned pastor, Ma$e?
Harlem World - Jealous Guy (feat. 112)