He made most of his money off of his career as a pop artist, but he has also amassed much wealth because of good business decisions (i.e. when the Beatles record label decided to sell the rights to their entire collection, he out bid paul mccartney for them, so every time a beatles song is used or sold, he gets cash).
debt, i dont know.
I dont think he was ever charged criminally in the first one, he was investigated, but never charged.
Settlement was undisclosed.

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