Vanilla Ice
Who can forget the catchy ‘90s hit, ‘Ice Ice Baby,’ recorded by Robert Matthew Van Winkle – AKA Vanilla Ice. While he may still be raking in big bucks in royalties for his music and TV appearances, it’s trouble in paradise for the Texan rapper.
According to reports, Vanilla Ice has been trying to avoid paying his ex-wife the money he owes her. This led to a judge stepping in and making Van Winkle pay ex, Laura, hundreds of thousands of dollars in unpaid fees. Ouch!
Mike “The Situation” Sorrentino
When Mike Sorentino, nicknamed “The Situation,” was at the height of his powers, he was fresh off starring in the hit reality show Jersey Shore, and was practically a monster celebrity. They even roasted him on Comedy Central!
But after some questionable decisions he made such as not paying taxes on his $8.9 million income, he was sent to jail. However, if you ask him, he’ll say that he plans on making a comeback in 2019.