Vanilla Ice

Robert Matthew Van Winkle, more popularly-known as Vanilla Ice, was a rapper and actor who first rose to stardom after re-releasing his debut album under the new title, To the Extreme. The album contained the hit singles Ice Ice Baby and Play That Funky Music, both of which performing well in the charts, with the former hitting No.1 in 1989.

The one-hit-wonder still made news after his initial success, but none were for the right reasons. Winkle began to rack-up a string of criminal charges, such as illegal drag racing, domestic abuse, driving without a license, brandishing a weapon and burglary.