In becoming the first rapper to reach No. 1 on the Billboard Hot 100, Vanilla Ice played a key role in pushing hip-hop into the mainstream. However, with superstardom came a backlash that dogged his career for years. • Growing up in Texas and South Florida, the artist born Robert Van Winkle excelled at motocross and breakdancing. • Ice eventually began rapping and made his name at the South Dallas nightclub City Lights. • He initially released “Ice Ice Baby”, the song that would make him famous, on the 1989 indie album <i>Hooked</i>. It became a massive hit after it was rereleased by SBK Records the following year on the album <i>To the Extreme</i>. • In 1990, “Ice Ice Baby” became the first rap song to top the Billboard Hot 100. Ice has claimed he wrote the mammoth hit—which samples the Queen and David Bowie classic “Under Pressure”—when he was just 16. • Thanks to the success of “Ice Ice Baby” and the follow-up hit “Play That Funky Music,” <i>To the Extreme</i> remained atop the Billboard 200 for 16 weeks. It’s sold more than 15 million copies worldwide. • Ice made his Hollywood debut playing himself in 1991’s <i>Teenage Mutant Ninja Turtles II: The Secret of the Ooze</i>. That same year, he starred in the film <i>Cool as Ice</i>. • Four years after his commercially disappointing sophomore album, 1994’s <i>Mind Blowin’</i>, Ice pivoted to rap-metal with <i>Hard to Swallow</i>. • Decades later, Ice has remained a part of pop-culture. In 2010, he launched the DIY Network series <i>The Vanilla Ice Project</i>, where he puts his contracting skills to the test by flipping properties as a real estate agent, and in 2016, he competed on Season 23 of <i>Dancing with the Stars</i>.