Cars: Bugatti Veyron, Mercedes-Benz Sprinter, Maybach 62S Landaulet, attempted Maybach Exelero

There is nobody better on this list at spending exorbitant amounts of cash on the newest, fastest, and most expensive rides on the planet. He claimed at one point to have 50 whips, and that was when Lil Wayne was 16 years old. Take that thought, consider how much more money he's made off Young Money since then, and you get a dude that's rubbing his hands looking at new candy apple red rides more often than you hail a taxi.