MC Hammer
MC Hammer, $10 million
Stanley Burrell, as MC Hammer, had the classic local-boy-makes-good storyline: He saw a meteoric rise, set off the craze for parachute pants, and — pre-dot-com bubble — paid $9.3 million for a mansion in a Northern California suburb to which he added more than that amount in custom features. To be fair, many of his expenses were from employing people from the neighborhood, but within six years of his hip-hop album being certified diamond — a first — a different kind of hammer came down as he and his wife filed for Chapter 11. Hammer's story always makes the cautionary "celebrities who become bankrupt" list, but he's often been in on the joke. There was that beef with Jay-Z when the mogul alluded to Hammer's past finances and his faith, and he replied in kind with a song and video involving the devil — and the beef blew over.
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