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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.

In 1985, he was focusing all of his energy on motocross, winning three championships. After breaking his ankle during a race, Ice was not interested in racing professionally for some time, using his spare time to perfect his dance moves and creating his own while his ankle was healing. Ice used his beatboxing and breakdancing skills as a street performer with his friends at local malls during this time. One evening he visited City Lights, a South Dallas nightclub, where he was dared to go on stage by his friend Squirrel during an open-mic. He won the crowd over and was asked by City Lights manager John Bush if he wanted to perform regularly, which he accepted. Ice would be joined on stage with his disc jockey D-Shay and Zero as well as Earthquake, the local disc jockey at City Lights. The Vanilla Ice Posse or The V.I.P. would also perform with Ice on stage. As a performer for City Lights, Ice opened up for N.W.A, Public Enemy, The D.O.C., Tone Loc, 2 Live Crew, Paula Abdul, Sinbad and MC Hammer.  In January 1987, Ice was stabbed five times during a scuffle outside of City Lights. After spending ten days at the hospital, Ice signed a contract with the owner of City Lights, Tommy Quon and his management company, Ultrax. Two years later, Ice would open for EPMD, Ice-T, Stetsasonic, and Sir Mix-A-Lot on the Stop the Violence Tour. Quon saw commercial potential in Ice's rapping and dancing skills. Buying studio time with Quon's earnings from City Lights, they recorded songs that had been perfected on stage by Ice and his acquaintances with various producers, including Khayree. The two year production was distributed by an independent record company called Ichiban Records in 1989. "Play That Funky Music" was released as the album's first single, with "Ice Ice Baby" appearing as the B-side. Tommy Quon personally sent out the single to various radio stations around the US, but the single was seldom played and when it was, it did not get the reaction Quon was hoping for. When disc jockey Darrell Jaye in Georgia played "Ice Ice Baby" instead of the single's A-side, the song gained a quick fanbase and other radio stations followed suit. Quon financed $8,000 for the production of a music video for "Ice Ice Baby", which received heavy airplay by The Box, increasing public interest in the song.  Following the success of "Ice Ice Baby", record producer Suge Knight and two bodyguards arrived at The Palm in West Hollywood, where Ice was eating. After shoving Ice's bodyguards aside, Knight and his own bodyguards sat down in front of Ice, staring at him before finally asking "How you doin'?" Similar incidents were repeated on several occasions. Eventually, Knight showed up at Ice's hotel suite on the fifteenth floor of the Bel Age Hotel, accompanied by a member of the Los Angeles Raiders football team. According to Ice, Knight took him out on the balcony by himself, and implied that he would throw him off the balcony unless he signed the publishing rights to the song over to Knight; Knight used Ice's money to help fund Death Row Records.
Vanilla Ice