50 Cent
50 Cent came from nothing, and he has amassed a massive net worth by being a smart businessman. After he sold his stake in the Vitamin Water company for a reported $100 million dollars, he could purchase any car he wanted (via Auto Evolution).

50 Cent was always fond of fast cars and his Lamborghini Murciélago is perhaps the most notable example of this. The cars were one of the most popular sports cars of their era. He also owned a few other expensive sports cars.