Fiddy's rags-to-riches story is one of the most dramatic on this list. The rapper was selling crack as a 12-year-old in his native Queens until he scored his first music industry break in 2000, when he was scheduled to shoot a video for his song "Thug Love" with Destiny's Child. Two days before filming began, however, he was famously shot nine times. Following his miraculous recovery, Fiddy got a second chance thanks to Eminem, who signed him to Interscope Records. The rapper's debut album, Get Rich or Die Tryin', sold 15 million copies worldwide. But his income from rapping is just chump-change compared to the bills he rakes in as a savvy entrepreneur.