An actor who is known to portray some of the most awkward-looking roles on screen, Johnny Depp can look smashing and ugly at the same time. He can also look smashing while dressed up ugly, something only he can pull off! He has also played the role of the infamous pirate Captain Jack Sparrow in the Pirates of the Caribbean series in a manner nobody else could. Despite his great roles and high earnings, he has the bad habit of mismanaging his money. This has often left him with huge debts, but he is always saved through a few smart real estate investments.