The Rapper: Cam'Ron
The Record Label: Roc-A-Fella Records
WTF? We all know why Cam decided to sign with the Roc (what up, Dame?!) and we're certainly not complaining (Cam's best album, Purple Haze, came out during his time on the label). But in hindsight, how did Cam ever agree to be put onto a label run by Jay-Z? At the time, Dipset had a nice little following and plenty of hype surrounding their movement, so it was slightly surprising to see them agree to hitch their wagon to the back of someone else's movement. Just sayin'.