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11. MC Hammer – You Can’t Outrun the IRS
I know, I know. It’s hard to feel bad for a guy who wore genie pants — for the guy who started the whole genie pants fad, in fact — but the fact of the matter is that good old MC Hammer had a really rough go for a while. The man most responsible for one of the dumbest looks in modern music history was also responsible for the mega-hit “U Can’t Touch This” way back in 1990. That song was everywhere. In fact, now that I think of it, it kind of still is. Anyway, Hammer had a string of hits, including the monster smash “Too Legit to Quit.” Apart from the fact that neither you, I, nor Hammer himself ever actually considered him to really be all that legit, the money gods were already closing in on him. When I say “money gods,” I mean, of course, the IRS, which in the late nineties declared that Hammer owed them about $9 million in back taxes. Hammer declared bankruptcy basically immediately.
10. Larry King – Grand Larceny?
If you’ve ever seen Larry King on late-night TV shilling that Omega XL joint pain stuff, then you might think the masterful radio and TV personality with the eponymous show was hurting for money. Well, that’s certainly not the case now, as good old Larry was worth a reported $150 million in 2015, but he actually did have to declare bankruptcy some years back — 1978 to be precise. Apparently, Larry had over $350,000 in debt back then. He was working at the time as a radio host in Miami and was even publicly accused by a “business partner” of grand larceny. Now, I don’t know what “business” a radio personality in Miami was in, but the whole situation sure didn’t help Larry much. At least not at the time, anyway. Later that same year, though, he was offered the gig that he held onto forever, earning him back every penny of that $350,000 plus just a little bit more in interest.
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