Elton John (Bankrupt in 2002): Sir Elton was living high on the hog with a 37-acre estate in Windsor, among other properties in the U.K., America and France, and a fleet of 20 luxury cars to ferry him around. Too bad he couldn’t afford it. The BBC reported that prior to bankruptcy, his credit card bills were rumored to top $400,000 every month and he spent a staggering $55 million in the span of 20 months! He took legal action against a money manager … but c’mon, Elton. In the court case it was revealed he spent $450,000 on flowers alone during the 20-month binge.
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