14. Kim Basinger

Don't buy a town or a city. We don't care how rich you are, or how great an idea it looks at the time, there's just no good reason for someone to drive up to a whole town, decide you like the look of it, and offer to purchase the entire thing lock, stock, and barrel because you've got some money in the bank and some big ideas. That's how Kim Basinger lost every single one of the millions of dollars she made in her 1980s heyday.

Basinger had big dreams for the small Georgia town, which she believed she could turn into something akin to Disneyland and Hollywood all rolled into one, with plans for major film studios and a huge theme park. She paid $20m to buy it - an even bigger sum in the early 1980s than it is now - but her big dreams failed to become a reality. When she was forced to file for bankruptcy in 1983, all of her assets were sold. That included the town, which went for a $19m loss. Ouch.

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