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Toni Braxton

In 2007, things were starting to look up for “Un-break My Heart” singer Toni Braxton. Despite selling 25 million albums worldwide, she had declared bankruptcy in 1998 after racking up a $20,000 American Express bill and monthly expenses of over $43,000. However, she soldiered on with her career and released a popular new album in 2000, The Heat. Finally, she was back on track, and she could put her financial troubles behind her.

Braxton’s career renaissance was so successful that she was asked to headline the Flamingo Hotel in Las Vegas in 2006. The show proved so popular that its run was extended through 2008. However, in April of that year, she was hospitalized for chest pains, and as a heart disease sufferer she decided not to further endanger her health. She decided to play it safe and cancel the remaining run of her show, but the cancellation incurred debts in the tens of millions of dollars. Braxton filed for bankruptcy a second time in October 2010.

Photo: Getty Images