Mike Tyson

The former world heavyweight  once had an estimated worth of $300 million. But with an incredibly lavish lifestyle — including pet tigers, a custom-built Bentley, and a removable glass roof on his mansion — his wealth quickly vanished. He filed for bankruptcy in 2003.

Rapper M.C. Hammer

Rapper M.C. Hammer reportedly spent more than $33 million in two years. When he filed for bankruptcy in 1996, he claimed to be about $14 million in debt.

Dorothy Hamill

The 1976 world figure-skating champion who bought the Ice Capades faced tough competition from Disney’s World on Ice. Hamill’s marriage collapsed, and she was forced to sell the Ice Capades at a loss and declare bankruptcy in 1996.

Francis Ford Coppola

Although the acclaimed movie director won five Academy Awards in the 1970s, he was less fortunate in the 1980s. Three big box-office flops — Rumblefish, The Outsiders and One from the Heart — forced him to seek protection from creditors under Chapter 11.  He filed for bankruptcy in 1990 while shooting The Godfather III.

Kim Basinger

In the early 1990s, the Oscar-winning actress was ordered to pay Main Line Pictures about $8 million for backing out of the movie Boxing Helena. The ruling forced her to sell Braselton, Georgia — a town she bought as an investment — at a loss of about $19 million. She filed bankruptcy in 1993.

Anna Nicole Smith

In 1996 the Playboy Playmate  was ordered to pay $830,000 to a former employee who accused her of sexual harassment. Although Smith was battling for a cut of the billion-dollar estate of her deceased husband, oil tycoon J. Howard Marshall, she filed for bankruptcy.

Burt Reynolds

After his highly publicized divorce from Loni Anderson in 1993, the actor sank deeply into debt, owing an estimated $10 million. He declared bankruptcy in 1996.

Don Johnson

The Miami Vice star  filed for bankruptcy in 1994 to protect his $20 million Colorado ranch from creditors. Johnson managed to get his finances in order, pay off his debts, and emerge from Chapter 11 still owning his ranch.

Gary Coleman

Citing years of financial mismanagement, the former child star filed bankruptcy in 1999. At the time he said, “This is the last step in 10 years of steps to mitigate and eliminate the dead weight of the past.”