Age: 31
Albums: Split Personality (2004), I'm a Hustla (2005), B.A.R.S. The Barry Adrian Reese Story (2007), C.A.S.H (2010).

In 2003, Cassidy had a battle rap pedigree, verses on Ruff Ryders albums, and a buzz based primarily on beating fellow Philly hardcase Freeway in a battle. But he decided to go straight for the crossover money with his debut single, grinning like Ma$e in the R. Kelly-featuring "Hotel," without even trying to cement his rep as a spitter.

The backlash was strong and the sales were weak, but Cass showed remarkable resilience when he came back harder with hits like "I'm A Hustla" and "My Drink N My 2 Step," and persevered through personal setbacks like a murder case and a terrible car accident. But the patronage of Swizz Beatz only took him so far, and eventually his inability to translate his lyrical talent to a great album left him out in the cold. He was last seen up to his old tricks, trying to get shine off of a beef with Meek Mill, another Philly rapper with stronger studio output than him.