The investment: A Las Vegas fixture for years, film icon Debbie Reynolds put her money where her heart was, purchasing a Vegas casino in 1991 and christening it the Debbie Reynolds Hotel & Casino. She not only performed there, but also made the hotel the home of her massive collection of Hollywood memorabilia.
The dive: As the saying goes, it's all about location, location, location. The hotel was off the Vegas strip and as a result, business never really took off. Reynolds filed for bankruptcy in 1997, and the hotel was purchased at auction by the World Wrestling Federation in 1998 for $10 million -- less than was needed to pay off the property's claims. Sadly, the financial woes didn't end there. Reynolds was reportedly heartbroken as she began to sell off her vast memorabilia collection in September 2010 after the museum that was to hold it went bankrupt as well.
As of 2013, Reynolds has published a memoir, "Unsinkable," and is in the black again, according to IndieWire. Despite being $5.3 million in debt on the costume museum, she made $4.6 million on the sale of one iconic costume alone: the famous dress Marilyn Monroe wore while standing on the subway grate in the movie "The Seven Year Itch."