12. MC Hammer: U Can’t Touch This was clearly not written about Hammer’s bankroll: the Bay Area-based rapper reported a debt of more than $13.7 million during a 1996 bankruptcy court hearing, less than seven years after the release of his multi-Platinum selling album, Please Hammer Don’t Hurt ‘Em. 14. Mindy McCready: The Celebrity Rehab star’s well-known battles with substance abuse have overshadowed her financial struggles, as she filed for bankruptcy in 1997, a year after breaking onto the music scene with hits like Guys Do It All the Time, Maybe He’ll Notice Her Now and A Girl’s Gotta Do.
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