50. Susan Powter
Susan Powter wrote three books in the 1990s, which became New York Times best sellers, and made Powter the diet and exercise go-to girl.(“Stop the Insanity!”) The crew-cutted, bleach blonde Powter filed for bankruptcy in 1995 because legal fees “have wiped me out.”
51. Randy Quaid
Randy Quaid is known for his role as Cousin Eddie in the Vacation film series and is Dennis Quaid’s big brother. His wife directed him in the 1999 movie The Debtors but unfortunately it was never released and the couple had to file for bankruptcy because they were $1 million in debt.
Rembrandt went bankrupt in 1656 and his house and collections were auctioned. Unfortunately, the money raised wasn’t enough to cover his debt so he set up an art-dealing business to keep his creditors at bay.
53. Tommy Rettig
Tommy Rettig portrayed the character “Jeff Miller” in the popular Lassie TV series from 1954 to 1957 and went down a similar path that many child actors tread. He got into drugs and went bankrupt as a result of being unable to find work as an adult actor
54. Burt Reynolds
Burt Reynolds was $10 million in debt when he filed for bankruptcy after his 1996 divorce. He went on to win a Golden Globe for Best Supporting Actor in the movie Boogie Nights.
55. Mickey Rooney
Mickey Rooney filed for bankruptcy in 1996 because he owed over $1.75 million to the IRS.
56. Anna Nicole Smith
Anna Nicole Smith was ordered to pay $850,000 to an employee for a judgment against her for sexual harassment in 1996 and since she had yet to be given any of her late husband’s billions, she had to file for bankruptcy.
57. Dee Snider
Dee Snider, lead singer of Twisted Sister, went bankrupt in the late 90’s after he was unable to follow the success of his 80’s career with a band that sold records.
58. Lynn Spears
Lynn Spears and her husband filed for bankruptcy in 1998 right before her daughter, Britney, became a superstar.
59. Sheryl Swoopes
Sheryl Swoopes, a three-time Olympic gold medallist and three-time MVP of the WNBA, filed for bankruptcy in 2004 reportedly owing $711,050. She blamed mismanagement of her money as the cause.
60. Lawrence Taylor
Lawrence Taylor played for the New York Giants from 1981 to 1993 and then substance abuse took over his life. He was arrested in 1998 for failing to pay child support and had to file for bankruptcy because of the high amount that he owed to support his kids each year. He was still voted into the NFL Hall of Fame in 1999 despite his personal problems and has been clean ever since.
61. Donald Trump
Donald Trump found himself $900 million in debt in 1990 and lost a lot of his business ventures but somehow restructured his debt to be back on top running a billion-dollar empire.
62. Mark Twain
Mark Twain went bankrupt in 1894 thanks to bad investments, especially in new inventions, and his publishing house going under. Twain went on an around-the-world lecture tour to pay of his creditors and did so in full in 1898.
63. Mike Tyson
Mike Tyson earned a reported $300 million in his boxing career but it somehow wasn’t enough for his lavish lifestyle. He filed for bankruptcy in 2003 owing a debt of $27 million. Tyson’s lifestyle cost $400,000 a month to maintain and during his divorce, he paid $9 million in legal fees alone.
64. Oscar Wilde
Oscar Wilde, in trouble for “gross indecencies,” was forced to declare bankruptcy in 1895 and lost some of his prized possessions including first editions of his own books. After serving his prison term, his friends helped him to bring his estate out of bankruptcy.
65. Ray Winstone
Ray Winstone started his acting career with a riveting performance in the 1979 movie Scum. Unfortunately, he had trouble after that getting work and forced into bankruptcy at the end of the 80’s. He was most recently seen in Beowulf and Indiana Jones and the Kingdom of the Crystal Skull.