Becoming Riff Raff: How a Quiet, White Suburban Kid Morphed Into Today's Most Enigmatic Rapper

As a prepubescent boy in the early '90s, Horst Simco was enamored of South Florida resident Vanilla Ice. Like millions of other kids, Horst fell for the white Palm Beach County rapper's slick dance moves and outrageous style — Evel Knievel-style jumpsuits; blow-dried, gravity-defying hair; slits cut into his eyebrows.

But before long, Ice fell out of favor amid questions of his authenticity. Though the man born Robert Van Winkle claimed to be a poor kid who'd attended high school in Miami, he'd actually grown up in a middle-class Dallas suburb. It wasn't exactly the streetwise image he was trying to project.

Young Horst, who played Miami's Eve event space in August, maintained affection for his hero long after it ceased being cool. But when it came to charm and charisma, he was no Vanilla Ice. Family members recall a well-behaved, quiet kid who never got in trouble. And while the rap scene in Houston was bubbling up, Horst might as well have been a million miles from it: The family's ranch house was on a quiet cul-de-sac in the northwest suburbs, about 25 miles outside downtown, with a towering ash tree out front and a big backyard. There wasn't much to do in the area; not long before Ronald and Anita Simco bought there in 1984, the area was mostly rice farms.

Marco Torres

When Riff Raff (with Bun B) "started to get into rap, he started to emulate the black culture."

Marco Torres

In 2011, Riff Raff arrived in L.A. to stay. He won over critics via collaborations.

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Horst wasn't much into making music — no one in the family really took to any musical instruments, his brother says — but he was obsessed with basketball, playing frequently with a group that included his next-door neighbor, Juan Sosa.

"He was nothing like he is today," says Sosa, now 34. He describes Horst as a "bookworm" and a "shy, clean-cut kid" who wore collared shirts and blue jeans.

The Simcos moved away, and the boys fell out of touch. But years later, in 2009, Sosa was shocked to see his former basketball buddy on MTV reality show From G's to Gents. His look and manner couldn't have been more different.

In the ensuing decade, Horst Simco had transformed into Riff Raff: a controversial, wild-eyed rapper dripping in diamonds, his body coated with outrageous tattoos. With cornrows, a whimsical zigzag beard and notched eyebrows just like Vanilla Ice, he'd become an internet sensation — a virtual caricature of a hip-hop star, a lightning rod called both brilliant and a brain-dead minstrel act.

Riff Raff is an endlessly quotable, sui generis pop-culture figure, a bona fide celebrity who pals around with Drake and Justin Bieber. His YouTube videos get millions of views.

There's something polarizing about him: Depending upon your point of view, Riff Raff seems either to embody the worst racial stereotypes or to transcend them. He peppers his rhymes about money, cars, and women with surrealist humor that's crass but often hilarious — on his recent single "Dolce & Gabbana" he rhymes, "Your bitch playing strip poker/I'm outside eatin' fried okra/(With who?) With Oprah!" But despite some extremely catchy songs, he's had no chart success to speak of, and many folks paying attention to him don't necessarily find his music compelling. They just want to know if he's serious.

Today, Riff Raff sits sulking on a couch. He's in the lobby of the Los Angeles headquarters of his record label, Mad Decent. Most artists in his situation would be waxing about their forthcoming album, particularly when it's got as much buzz as Riff Raff's Neon Icon. Although it doesn't yet have a firm release date, it's expected to feature a bevy of hot rappers and producers, including Wiz Khalifa, Skrillex, and DJ Mustard. After countless mixtapes, this is Riff Raff's first official release — and his introduction to a wider audience.

Instead, he's brooding. Though his publicist was told otherwise, he thought this meeting would be for a cover shoot, and he'd clearly labored over his look: His beard is just right, and his braids are done up with white and black beads. His orange T-shirt with cutoff sleeves matches his multicolored board shorts and his Nikes. He's eating from a bag of candy oranges, the two-for-a-dollar kind, and drinking a Snapple; even his snacks match his outfit.

Another problem: This interview isn't being videotaped. "Y'all should've added a video or some shit," he says. Indeed, video is where Riff Raff's charisma shines through. He's pure id, full of restless energy, and his non sequiturs are perhaps best understood via six-second looping clips on Vine.

So right now, he's miserable. "I feel like I'm in a police station interrogation or something," he says, sounding downright depressed. Even worse is when he's asked specific questions about his past. It's safe to say there's nothing Riff Raff would rather talk about less.

What's strange is that, for a guy as famous as he is, almost no one knows the most basic information about him. This is largely because he's been dispensing evasive answers since he began giving interviews. "My mom was a pilot, and my dad wrestled polar bears," he answers when asked what his parents did for a living. Other times, he stretches the truth and lies with more conviction.