© Frank Trapper/Corbis
The investment: Burt Reynolds, the world's most popular movie star in the 1970s, invested in a restaurant chain ironically called PoFolks, opening outlets throughout California, Texas and Florida. By the late '80s, that investment made Reynolds a po' folk himself, costing him $15 million.
Combined with other bad investments, his diminished luster as a star and a costly divorce from Loni Anderson, the investment drove him toward a 1996 bankruptcy filing, at which time he was more than $10 million in debt.
The dive (or lack thereof): "The Bandit" always had a certain charm for lucking out of tough situations, and that didn't stop off-screen. Despite the bankruptcy, Reynolds was allowed to keep his $2.5 million mansion and all his personal property.
In August 2011, Merrill Lynch Credit Corp. filed a foreclosure lawsuit against Reynolds for failure to pay his mortgage since 2010 on his 4-acre Florida waterfront estate. In 2014, a judge threw out Reynolds' request to remove the foreclosure, allowing Merrill Lynch Credit Corp. (now Bank of America) to proceed with the lawsuit.