Toni Braxton
It's a good thing Toni's heart is unbroken, because the rest of her is flat broke. The six-time Grammy winner and her company Liberty Entertainment filed for bankruptcy last September after accumulating debts ranging from $10 million to $50 million against only $1 million to $10 million in assets. That's actually the least of Braxton's problems.

This is the singer's second bankruptcy after first filing in 1998, but that was brought on by tension and an eventual split with her record label and poor financial choices, such as accumulating $500,000 in overdraft fees in 1997 alone. This time, much of Braxton's trouble stems from canceling a string of shows in Las Vegas in 2008 after chest pains she experienced during performances were later diagnosed as a heart problem that insurer Lloyd's of London called a "pre-existing condition" in refusing to cover her losses. She was also forced to pull out of the series finale of ABC's Dancing With The Stars that year when she had a breast tumor removed. With a list of creditors including the Internal Revenue Service, Flamingo Las Vegas hotel and casino, the Four Seasons Hotel in Washington, D.C., Cedars-Sinai Medial Center, Neiman Marcus, the Screen Actors Guild, RCA Music Group and Tiffany & Co. ( TIF), Braxton saw her $2.6 million home in Henderson, Nev., go into foreclosure and sell for little more than $1 million. Her $1.2 million home in Duluth, Ga., just went into foreclosure proceedings.

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