I think you'll find one common factor among these people (except Nicolas Cage): They all grew up without money and/or contacts, then got money and didn't know how to handle it and/or were unclear how much their "friends and trusted advisors" will be happy to "take a piece of them" and then disappaear when the going gets tough.

Add in a lot of substance abuse (often goes with making a shitton of money starting when you're pretty young).

Finally add in the ego factor that when you start to make a lot of money it is hard to imagine it all going away. You either have to be very grounded, have VERY good mentors, or have just the right balance of character flaws.