5. Debbie Reynolds

Debbie Reynolds shot to stardom during the 1940 and 50s. Her singing and dancing talents were something that helped her pave her way ahead. She is still very active on television and stage. So, after ruling the hearts of many, she decided to try her fortune in the casino business. She bought a casino in Las Vegas in the year 1991. She renamed it as Debbie Reynolds Hotel & Casino.

The Hiccup: To promote her casino, Reynolds performed there and also housed her Hollywood memorabilia from the MGM era there. As does the famous saying go – ‘it’s all about the location,’ Reynolds’ casino was at a slight disadvantage. Her casino was off the Vegas strip. This led to the business getting adversely affected. As a result, Reynolds had to file for bankruptcy in the year 1997. Additionally, she also lost her precious memorabilia in order to pay her debts.