Evolving in the public eye, Chris Brown has gone from teenaged heartthrob to pop music megastar to vilified brute and then repentant sinner. At the heart of his image downturn is the 2009 assault of then girlfriend, Rihanna, which showed a darker side to the talented singer/dancer/actor. Brownâ€™s subsequent apologies, paid debt to society in the form of community service and an emotional performance of Michael Jacksonâ€™s â€œMan In The Mirrorâ€ at the 2010 BET Awards seemed to have almost wiped his slate cleanâ€”that is, until last monthâ€™s Good Morning America appearance. Following an awkward and defensive interview with GMA co-host Robin Roberts, Brown threw a tantrum backstage, smashing a window at ABCâ€™s Times Square studio in the process. Though Brown has since apologized for his behavior (again), many speculate that heâ€™s running out of second chances and thatâ€™s bound to hit him in the pockets. BlackEnterprise.com takes a look at how all the drama has or hasnâ€™t affected the troubled starâ€™s money.