1. Sinbad

Sinbad is of funny. But there’s nothing humorous about this: he’s filed for bankruptcy twice.

2. Octomom

Octomom filed for bankruptcy in 2012. She was later arrested for welfare fraud.

3. Mekhi Phifer

Mekhi has just recently filed for bankruptcy. He submitted court papers in April, claiming his debts have spiraled to $1.3 million – including $1.2 million in back taxes, $50,000 on lawyer fees and another $4,500 in child support.

4. Vince Young

The former star pro football player filed for Chapter 11 bankruptcy earlier this year. His attorney listed Young’s assets as being worth between $500,001 and $1 million with liabilities between $1,001,000 and $10 million.

5. Dionne Warwick

Warwick was forced to file for bankruptcy in the spring of 2013 due to over $1 million in tax liens dating back two decades. Her financial woes originated from a business manager who mismanaged her affairs.

6. Toni Braxton

Toni Braxton has filed for bankruptcy twice in past 15 years, first in 1998 and again in 2010. She’s cited bad recording contracts and health issues as the reasons for her financial woes.

7. La Toya Jackson

La Toya Jackson once had dreams of a big singing career. However instead of making millions, the pursuit of her career cost her than she’d bargained for. She was forced to file bankruptcy in 1995.

8. The Late Great Marvin Gaye

Marvin Gaye’s bankruptcy came after a marriage gone wrong. In 1976, the royalties for his album Here, My Dear were promised to his ex-wife Anna Gordy as a substitute for alimony.

9. TLC

The ladies of TLC experienced the perfect example of management gone wrong. Even after selling more than 10 million records, the trio was forced to file for Chapter 11 in 1995 due a series of bad business deals.

10. Gary Coleman

Child star Gary Coleman filed for bankruptcy in 1999. He cited mismanagement and medical expenses as the reason for his money troubles.

11. Natalie Cole

Natalie Cole was surprised to learn that majority of her earnings during the 1990s went to her late father Nat King Cole’s estate. The eight-time Grammy Award-winning singer was forced to file bankruptcy in 1997.

12. Michael Vick

Michael Vick filed one of the biggest bankrupcies ever.

13. Chris Tucker

Chris Tucker, he bank claims he owes more than $4.4 mil on his new home.

14. Kim Basinger

Kim Basinger was one of the top earning stars in the 80’s but mismanaged her money and spending i.e. purchased a town in Georgia?

15. Larry King

Talk show host Larry King filed for bankruptcy in 1978.

16. L.T.

Former NY Giants linebacker Lawrence Taylor filed for bankruptcy in 1998.

17. Marion Jones

Legal fees stemming from steroid use led Marion Jones into Bankruptcy.

18. MC Hammer

19. Mike Tyson

Mike Tyson was once one of the top grossing boxers earning over $300 million.