19. Ferrari Enzo
Years Of Production: 2002-2004
Famous Owners: Paul Allen, Nicolas Cage, Eric Clapton, Joe Cole, Tommy Hilfiger, Mika Hakkinen, Nick Mason, Pope John Paul II, Michael Schumacher, Rod Stewart, Axl Rose, 50 Cent
Complex Says: The Enzo is one of those cars that was not just freakishly expensive, but freakishly ostentatious, and of freakish amounts of infamy. It's known for its ability to send the extremely wealthy into trees and lamp-posts at high speeds almost as much as its performance and exclusivity.