<div class='timeline-item'><div class='timeline-left'><div class='timeline-date'>1968</div></div><div class='timeline-center'></div><div class='timeline-right'><div class='timeline-text timeline-text-title'>Vanilla Ice is Born</div><div class='timeline-text'>On October 31, 1968, Robert Van Winkle was born in Dallas, Texas.</div></div></div><div class='timeline-item'><div class='timeline-left'><div class='timeline-date'>1989</div></div><div class='timeline-center'></div><div class='timeline-right'><div class='timeline-text timeline-text-title'>Releases "Ice Ice Baby"</div><div class='timeline-text'>Vanilla Ice releases his most iconic hit, “Ice Ice Baby.” The song becomes the first hip hop single to reach number one on the Billboard Hot 100.</div></div></div><div class='timeline-item'><div class='timeline-left'><div class='timeline-date'>1990</div></div><div class='timeline-center'></div><div class='timeline-right'><div class='timeline-text timeline-text-title'>Awards and Record Deal</div><div class='timeline-text'>At the 1991 American Music Awards, Vanilla Ice wins Favorite Rap/Hip Hop Artist and Favorite Pop/Rock New Artist. He also signs a record deal with SBK Records.</div></div></div><div class='timeline-item'><div class='timeline-left'><div class='timeline-date'>1991</div></div><div class='timeline-center'></div><div class='timeline-right'><div class='timeline-text timeline-text-title'>Movies and TV Appearances</div><div class='timeline-text'>Vanilla Ice stars in his own feature film, “Cool as Ice,” and makes an appearance in “Teenage Mutant Ninja Turtles II: The Secret of the Ooze.” He also appears on Saturday Night Live.</div></div></div><div class='timeline-item'><div class='timeline-left'><div class='timeline-date'>1998</div></div><div class='timeline-center'></div><div class='timeline-right'><div class='timeline-text timeline-text-title'>Vanilla Ice Goes Country</div><div class='timeline-text'>Vanilla Ice releases his fifth studio album, “Hard to Swallow,” which features a more hard rock and country sound than his previous albums.</div></div></div><div class='timeline-item'><div class='timeline-left'><div class='timeline-date'>2011</div></div><div class='timeline-center'></div><div class='timeline-right'><div class='timeline-text timeline-text-title'>Vanilla Ice on Dancing with the Stars</div><div class='timeline-text'>Vanilla Ice competes on the 13th season of “Dancing With The Stars.” He ends up finishing in 8th place.</div></div></div><div class='timeline-item'><div class='timeline-left'><div class='timeline-date'>2018</div></div><div class='timeline-center'></div><div class='timeline-right'><div class='timeline-text timeline-text-title'>Vanilla Ice Joins the Cast of Sharknado 6</div><div class='timeline-text'>Vanilla Ice joins the cast of “Sharknado 6: The Last Sharknado,” playing a character named “Randy the Cowboy.” </div></div></div>