The tale is as old as time. Celebrities and athletes who make ridiculous amounts of money find a way to blow it all and then file for bankruptcy. It's the typical notion of what it is to be 'new money'. This is not always the case, though, as some have been able to develop avenues that produce residual income through smart investments.
Some names that come to mind include Shaq and Jessica Alba. Well, go ahead and add Ashton Kutcher to the list. The 'Dude Where's My Car' and 'Punk'd' star, usually known for his comedy and quirkiness, has also been quite the savvy businessman by investing in companies that have produced him quite the profit margins.