Before Robert Van Winkle became a household name as Vanilla Ice, he was arrested in 1988 over an alleged Dallas parking lot assault, according to the Los Angeles Times. Claiming he was provoked, Van Winkle reportedly sprayed a “chemical irritant” in the eyes of a teenage boy, struck him in the head, and then pursued him and another teenager. He paid a $516 fine and served a year’s probation, UPI reported. Van Winkle’s debut album as Vanilla Ice, “Hooked,” came out the next year. But it wasn’t until his second album, 1990’s “To the Extreme” — featuring “Ice Ice Baby” — that he became a celebrity. The following year, Van Winkle was arrested again, this time for allegedly pulling a firearm on an unhoused individual in Los Angeles.
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At that time, Van Winkle and his bodyguard were charged with gun-related misdemeanors and released on their own recognizance. Facing prison time if convicted, Van Winkle later pleaded no contest in an agreement. The star would otherwise pay around a $1,700 fine, make an anti-drug community service video, and serve two years unsupervised probation, the LA Times reported that year. At the time of Van Winkle’s arrest, his then-lawyer Larry Friedman told the LA Times that the star “only and always acts as a gentleman.”
