Robert Matthew Van Winkle, AKA Vanilla Ice, released the catchy hit ‘Ice Ice Baby’ in the 1990s. Although the Texan rapper never had another real hit, he is still doing pretty well for himself through royalties and television appearances. His desire to get back at his ex, however, has caused him to make some bad decisions.
Reportedly, Van Winkle has been doing everything he can in order to not pay his ex-wife what he owes her. She took the issue to court, which made Vanilla Ice pay what he owes, plus hundreds of thousands of dollars in unpaid fees. Need some ice for that burn?
Amanda Bynes
The adorable and talented Amanda Bynes won all our hearts in Nickelodeon’s All That and The Amanda Show, and when she grew up a little, in What I Like About You on the WB channel.
She became more and more famous as time went on, starring in some feature films, but also dealt with substance abuse and mental issues. Bynes disappeared from the scene completely at one point and she is certainly not doing as well financially as she did in her heyday.
Joey Lawrence
Joey Lawrence was a staple of 90’s sitcoms and the crush of all teenage girls. He starred in "Blossom", "Melissa and Joey", and "Brotherly Love," and even appeared on the cover of TV Guide. But when the decade ended, Lawrence’s popularity waned, and his financial worries began.
In 2017, Lawrence filed for insolvency, and according to reports, the actor and his wife had just $8,000 in their bank account. The pair needed to sell clothes and some household appliances on eBay just to make a living.
Pamela Anderson
The former Baywatch beauty is yet another celebrity who mistakenly believed that being rich and famous is a good enough reason to not pay your taxes. The IRS corrected her misconception when they busted her for withholding hundreds of thousands of dollars in taxes.
Although it was a rough blow, Anderson never actually stopped enjoying her movie star lifestyle, so maybe there was something to her theory after all. And despite many believing otherwise, her net worth is reportedly only between $8 and $15 million.
Gaby Hoffmann
Gaby Hoffman started acting at a very young age, making unforgettable appearances in 80's and 90's classics like Field of Dreams, Uncle Buck, and Sleepless in Seattle. However, after her success in the coming-of-age classic Now and Then, Hoffman seemed to fade from the spotlight.
In 2013, she even claimed to have no more than "a few thousand dollars to my name", and was struggling to get work. In a twist of fate, a short time after, Hoffman scored an acting role on HBO's famous Girls, and then starred in the highly-acclaimed Amazon series, Transparent. All in all, it's safe to say Hoffman made a very successful comeback.