Chris Brown | Porsche 911 Turbo S | $230,000

Certified by the Recording Industry Association of America as platinum for his self-titled debut album in 2004, Chris Brown immediately rose to international fame. He also reached the top spot of the Billboard Hot 100 with his first-ever single, Run It. As if he were unstoppable, Brown has also been featured on several successful singles, including No Air with Jordin Sparks.

Considering the high life he is living, it is only normal for the singer to purchase luxurious cars. It is sad, though, that he had to use the insurance for one of his vehicles, a $230,000-worth Porsche 911 Turbo S, which was totally destroyed when he entrusted it to a valet while partying. This was a sad incident, but at least Brown has other equally classy vehicles in the garage. He probably learned a lesson or two as well on how to manage his fleet of cars better.