Age: 39
Albums: Soul On Ice (1996), Rasassination (1998), Institutionalized (2005), A.D.I.D.A.S. (All Day I Dream About Spittin) (2010)

Everyone can agree that Ras Kass is a great lyricist. He’s always had a cocky attitude that made him seem convinced that he was the greatest rapper ever. Too bad he couldn’t find the greatest producers. His first two albums were marred by shitty production unworthy for a rapper of his talents.

Right when he seemed like he was on the verge of putting it all together on third album, Van Gogh (which featured production from DJ Premier and Dr. Dre), he ran into label troubles and later an unfortunate arrest for D.U.I. which landed him in jail. The double whammy killed his momentum and his career has never been the same since.