A "batboy" for the Oakland A's as a preteen, which pop-rap artist scored a smash hit in 1990 and then blew through his $30 million earnings so fast that he landed in bankruptcy court in 1996?

Answer MC Hammer

Hammer's extravagance and unrestrained spending is the stuff of tabloid legend. It began with the purchase of a $1 million mansion—not unreasonable, given the $30 million in his bank account, right? But then he spent $30 million renovating the house. And hired a staff of 200. And then came the racehorses... 19 of them. Six years later, he was reportedly $13 million in debt.

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