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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.

After almost non-stop touring for the previous three years, Ice took a break from music in 1993 and began competing in jet skiing (becoming the 6th best jet ski racer in the world and obtaining sponsorship from Kawasaki) as well as resuming Motocross racing.  By 1994, Ice received less publicity and became removed from the public spotlight. After becoming more interested with the Rastafari movement, Ice became a vegetarian, grew dreadlocks and talked more openly about smoking cannabis. On March 22, 1994, Ice released his second studio album, Mind Blowin'. Reviews were unfavorable. Entertainment Weekly reviewer James Bernard called the album "more clunky than funky". Rolling Stone reviewer Danyel Smith praised the song "Get Loose" as "snappy", writing that although the lyrics are "inane", "the song is a thumping party, one of the few places where Ice loosens up. He sounds solid at the beginning of 'The Wrath' as well ... In 'Now and Forever,' a wet dream kind of song, Ice goes back to goofy lyrics." Allrovi reviewer Stephen Thomas Erlewine wrote that "There isn't a single moment that establishes a distinct musical identity, and the whole thing is rather embarrassing." Primus bassist Les Claypool stated in response to Ice's cannabis-oriented lyrics: "That's all fine and dandy and cute, but it could be misconstrued and manipulated by the wrong people." When asked about the drug oriented sound years later, Vanilla Ice said "A lot of the record is drug oriented because I was doing a lot of drugs at the time". Shortly afterward, SBK went bankrupt.  At around this time, Ice began using ecstasy, cocaine and heroin. During periods of heavy drug use, Ice received many tattoos from artist acquaintances. According to Ice, he "was in [his] binge days. [He] didn't even realize how many [he] was getting". Ice attempted suicide with a heroin overdose on July 4, 1994 but was revived by his friends. After being revived, Ice decided that it was time to change his lifestyle. As a symbol of his attempt to begin anew, he got a tattoo of a leaf on his stomach. After expanding his Mind Blowin tour overseas in 1995, Ice sold his estate in California and took a break from music, rather focusing on motocrossing and jet skiing in Florida. By the summer Ice was the world's No. 6-ranked sit-down Jet Ski racer, competing nearly every weekend and earning a Kawasaki sponsorship.  Uncertain about his future career, Ice studied real estate and started working on the side renovating and selling houses. In late 1995, Ice set up a recording studio in Miami and joined a grunge band, Pickin Scabz. The name was set to reflect Ice's career and how he was healing from his suicide attempt and that he was now "picking up the pieces". Ice expressed an interest in performing hip hop-influenced rock music, but found that the band was unable to produce the sound he was looking for. In 1996, longtime associate and friend Monte Lipman signed Ice as an artist for Universal Republic Records. He did guest vocals with no stage name for the song "Boom" by Bloodhound Gang on their CD One Fierce Beer Coaster.
Vanilla Ice