Alan Jackson – 1962 Corvette, $175K

When it comes to classics, country music star Alan Jackson knows what he wants. And with the seventy-five million dollars he has in the bank, Jackson can purchase any number of fantastic vehicles instantly.

However, Alan prefers his cars with a bit of history to them, and his taste is well-noted with the stunning red 1962 Corvette he owns. Cars from this era are worth loads of money, and this one set him back about one hundred and seventy-five thousand dollars. Give it a few years, and this investment will be worth even more!