On the surface, celebrities appear to have little to worry about in the finance department: They command massive paychecks, after all, and can often tap into impressive endorsement deals on the side.

The above is not true in most cases, When it comes to money, celebrities are just like the rest of us—they spend too much, save too little, and make plenty of poor money choices. In fact, their unpredictable incomes and expensive lifestyles can put them at even greater risk than the average person for financial downfall. These eight celebrities are among the most monetarily-challenged.

Below are 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.

Nicolas 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 strateg

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.

mismanagement is a bad bad thing. if not the above listed pple should never ever lack money.
i enjoy Toni's new reality shows with her sisters, hope she is able to get out of the water without drowning in american debt (not a joke)

Trump: someone should take that cap from his head. i don't pity him, marrying too many woman is a yardstick for poverty, he should ask an african man  and learn from them.

Lindsay, miss her in parent trap but the young shall grow and grow with lots of debt too (welcome to new generation)

Sarah, pity pity. anyway, glad she is still in good term with her ex. at least some shoulder to cry on.

Cage, aha!! spend so much on vodka so not surprise.

Spears: ummm, she should have married a guy with head on his shoulder not some boys with puppy love and gold digging tendency. glad she moved on and hope she learnt a lesson and never marry a jobless man who will be dragging you for child support.

Baldwin, i fell for that their trademark eyes. it pierce deeply unfortunately he couldnt see the debt coming. too bad