Robert Matthew Van Winkle, better recognized by his stage name Vanilla Ice, was born on October 31, 1967, in Dallas, Texas. He grew up in both Texas and South Florida, where he first ventured into music. His career kicked off with the release of his debut album, *Hooked*, in 1989. However, it was the re-release of the album in 1990 as *To the Extreme* under SBK Records that catapulted him to fame. This album became the fastest-selling hip-hop record in history and featured his iconic tracks "Ice Ice Baby" and a cover of "Play That Funky Music." "Ice Ice Baby" notably made history as the first hip-hop single to reach the top of the Billboard charts, playing a significant role in bringing hip-hop into the mainstream.
In addition to his music career, Vanilla Ice had a brief, high-profile romance with Madonna in 1990 and appeared in her controversial book, *Sex*. He starred in the 1991 film *Cool as Ice*, which, despite its poor reception and a Golden Raspberry Award for Worst New Star, showcased his attempt to break into acting.
After facing personal challenges, including a near-fatal overdose in 1994, Vanilla Ice reinvented himself, experimenting with a rock-oriented sound in later albums like *Hard to Swallow*, which achieved gold status. He also ventured into real estate, launching *The Vanilla Ice Project* on DIY Network in 2009 and publishing a related guide in 2011. His sixth studio album, *WTF - Wisdom, Tenacity and Focus*, was released in 2011. Vanilla Ice also appeared on *Dancing with the Stars* in 2016, and a biopic about his life starring Dave Franco is in development.
