15. 50 Cent
Cars: Rolls-Royce Ghost, Lamborghini Gallardo, Lamborghini Murcielago, Ferrari F430, Pontiac G8
See what happens when you make solid investments, kids? If you ever get famous, use your status to sign endorsements, drop out at the correct times, make a ton of money, and then go and buy a bevy of sick supercars. He even had a special edition Pontiac G8 made for him at SEMA one year.