4. Kim Basinger

Kim Basinger bought the town of Braselton, Georgia for $20 million, in 1989. She wanted to turn it into tourist attraction that featured movie studios and a film festival. But in reality, she only bought a bank building. Ameritech dumped down the cash, entitling her as “creative partner”, but later froze all development and nothing happened. After failing to get her Branson-esque project off the ground she sold the town for $1 million in 1993. Ameritech sold their share of interest in 1995 for $4.3 million.

5. Kevin Costner

Kevin Costner is the Founder & Chairman of Blue Planet Water Solutions. He has invested 15 years and $20 million toward the research and development of a rugged, compact, portable technology that would serve as a first line of defense against oil spills as mentioned in bpws.com, the official website of Blue Planet Water Solutions. “There's nothing to show for the millions I've invested. My God, most people would want to die if they lost $1,000 or $100,000. I've lost $40 million plus,” says Kevin, as quoted by Thedailybeast.com. “I'm not the shrewdest businessman; I'm more of a dreamer. I just am really happy that this has come to the light of day. I'm very sad about why it is, but this is why it was developed, and like anything that we all face as a group, we face it together,” he adds.