The Rapper: Freeway
The Record Label: Cash Money Records/Rhymesayers Entertainment
WTF? Since Freeway left Def Jam after the release of his appropriately-titled 2008 Def Jam album, Free At Last, the underappreciated rapper has had trouble finding a permanent home. Oddly enough, he's straddled the line between independent label (Rhymesayers released his album, The Stimulus Package earlier this year) and major label (Free signed a deal with Cash Money in 2009) rather well. But to be honest: Both of the labels that he signed with threw us for a loop.