4. Burt Reynolds

Burt Reynolds was the most popular Hollywood icon during the 1970s. He also made a decent transition to the world of television and has quite a few such laurels in his cap. Apart from the entertainment industry, Reynolds has made his name in the restaurant business as well. He invested in PoFolks, a restaurant chain, which had its outlets in Florida, Texas and California.

The Hiccup: PoFolks cost Reynolds a whopping $15 million due to top-level changes during the late 1980s. Reynolds had also lost a big chunk of money on other investments. He faced further financial woes after his divorce from wife, Loni Anderson. A combination of all these factors forced him to file for bankruptcy in the year 1996. He stood at a personal debt of $10 million at the time.