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Robert Matthew Van Winkle was born in Dallas, Texas, on October 31, 1967. Van Winkle has never known his biological father; he was given the family name of the Dutch man his mother was married to at the time of his birth. When Van Winkle was four, his mother divorced. Afterward, he grew up moving between Dallas and Miami, where his new stepfather worked at a car dealership.

With Quon back as manager, Ice was scheduled to appear in various reality TV programs. Ice, still an entertainer at heart, felt that the experience would be good for him. In 2002 he appeared on Celebrity Boxing, fighting Todd Bridges under the name 'Bi-Polar'. In 2003, he appeared in five episodes of Hollywood Squares, eight episodes on 'The Farm' and three episodes of Celebrity Bull Riding Challenge as well as a cameo in The New Guy in 2002. Around this time, Vanilla Ice also returned to the world of motocross. He auditioned for the 2002 X Games in the freestyle division and placed seventh at the 2003 Suzuki Crossover challenge, according to Sports Illustrated. He told the magazine that the track "is where I'm happiest." In 2003, Ice contributed vocals to "Off the Chain" by 7x70, a side project of Iron Maiden drummer Nicko McBrain and Anthrax guitarist Dan Spitz. A demo of the song was leaked in June. In 2003, Ultrax reissued Bomb Tha System (the second part of "Bi-Polar") under the title Hot Sex, which was a single from the original album. From January to February 2004, Ice appeared on the reality television series The Surreal Life. Although much of the series was staged, Ice found the experience to be therapeutic, stating that a comment made by Tammy Faye Messner during filming; "We are who we are because of who we were" helped him accept his past. On August 2, 2005, Ice released his fifth studio album, Platinum Underground. Ice stated that the title of the album reflected the fact that he could maintain a fanbase without mainstream airplay. Allrovi reviewer Rob Theakston panned the album, writing that it "has more bad spots in it than most". Ice made a song titled Ninja Rap 2 which was set to be a hardcore remix. Aside the name, the song has very little connection to Ice's original 1991 single, but rather talks about his appreciation to his fans, his love to perform at clubs and playing at the Gathering of the Juggalos with Insane Clown Posse. Ninja Rap 2 was the first song to be released from Platinum Underground and was available to download for free off of Ice's official website. In 2007, Ice returned to a spin-off of The Surreal Life titled The Surreal Life: Fame Games where he again trashed the set after being voted off. In September 2008, Ice signed a contract with Cleopatra Records, recording the cover album Vanilla Ice Is Back! at the label's request. The album was released on November 4, 2008, and contained covers of songs by Public Enemy, House of Pain, Bob Marley, and Cypress Hill. IGN reviewer Spence D. called the album "an embarrassing endeavor that sounds like it should have stayed locked inside Ice's studio (or at the very least leaked on YouTube and passed off as a piss take)." On February 27, 2009, Ice performed as part of a joint performance with MC Hammer in Orem, Utah called "Hammer Pants And Ice", which featured twenty four dancers and a full choir.
Vanilla Ice