Top 8 Celebrities with the biggest money problems

Toni Braxton

Toni Braxton filed for bankruptcy last year for the second time, and she owes as much as $50 million to companies including AT&T, Tiffany, and the Four Seasons. The famous singer has also faced liens from the IRS for unpaid taxes. Her financial troubles are now back in the spotlight as she stars on her family’s new reality TV show on WE TV.

Stephen Baldwin

In 2009, the youngest Baldwin brother filed for bankruptcy, which revealed he had more than $2 million in debt. Although he’s starred in various reality television shows and serves as a frequent spokesperson in the media, his spending seems to consistently outpace his earnings.

Britney Spears

Spears’s 2008 divorce filings showed that the pop star saved none of her $737,000 monthly income. Instead, she spent it on her homes, restaurants, and entertainment. After her more recent career comeback and her father’s guardianship over her, she appears to be getting her finances under better control.

Nicalas Cage

The actor has owned multiple homes (as many as 15 at once), almost two dozen cars (including nine Rolls Royces), and pricey art and jewelry, according to the celebrity website TMZ.com. Indeed, his lifestyle costs an estimated $30 million a year to maintain, according to his former manager. He’s also clashed with that manager in court over mismanagement accusations, but the lawsuits have now been settled.
 

Annie Leibovitz

The famous photographer ran into trouble after her partner, Susan Sontag, died, and Leibovitz was unable to inherit her estate without paying huge estate taxes. But Leibovitz’s financial troubles, which culminated in $24 million in debt, also came from unpaid taxes, outstanding rental equipment fees, an uncompleted book deal, and renovation payments.

Sarah Ferguson

After divorcing Prince Andrew, the Duchess of York was given an allowance, estimated to be worth around $24,000 a year. She also wrote books and rang up endorsement deals, but she was unable to afford her lifestyle and ran into such financial trouble that she was caught appearing to sell access to her famous family last year. She is now rebuilding her life, as her Oprah Winfrey Network show Finding Sarah documents.

Donald Trump

The real estate tycoon is known for exaggerating his net worth, which is estimated at around $1 billion. (Trump himself has said it is closer to $3.5 billion.) He has filed for corporate bankruptcy four times, most recently in 2009, which he has described as a valid business strategy.

Lindsay Lohan

In addition to her jail time and drug charges, Lohan is known for her big-spending ways. She’s purchased $30,000 Rolex watches and a $100,000-plus Maserati. She’s also struggled to match her earlier earnings since her personal troubles have prevented her from scoring as many starring roles.