The (Mostly) True Story of Vanilla Ice, Hip-Hop, and the American Dream

Ringer Illustration

By Jeff Weiss | The Ringer

In 1990, there was no star bigger than the man born Robert Van Winkle. But just as quickly as he became the bestselling rapper the world had ever seen, he became a pariah. Now, 30 years after “Ice Ice Baby,” he’s ready to talk about it all—and it may change how you feel about him.

I think I know enough of hate
To say that for destruction ice
Is also great
And would suffice

—Robert Frost, “Fire and Ice” 

“Robby Van Winkle and Vanilla Ice are the American dream come true.” —Vanilla Ice, Ice by Ice 

I. Something Grabs a Hold of Me Tightly 

Vanilla Ice was discovered on Martin Luther King Jr. Boulevard. It was the winter of 1987-88 in South Dallas, or maybe it was the following summer. All exact dates have dissolved into a haze of liquor, hair spray, and the tinnitus caused by long-gone 808 claps. The only thing anyone can agree on is that at the height of hip-hop’s first Golden Age, all the action in the Triple D went down at a club called City Lights.


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