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

Living in a tough part of Houston with a peer group almost entirely black, Horst painted cars in the in-vogue "candy-colored" style. He looked up to Northside Houston rappers from label Swishahouse, who were blowing up around that time, including Paul Wall, Chamillionaire, and Slim Thug.

It wasn't just their rhymes that Horst admired; it was their larger-than-life personas: They draped themselves in diamonds and drove ostentatious cars. They had women; they had money.

"Baller stuff," Riff Raff remembers. "The money, nice cars, getting crazy."

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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• Vanilla Ice
• Horst Simco
• Ronald Vaughns
• Hip-Hop and Rap
• Arts, Entertainment, and Media

Riff Raff didn't necessarily want to be a rapper: He just wanted the baller stuff for himself. "I didn't even think about music back then," he says.

It was around the mid-aughts that Riff Raff debuted his now-famous look. He began doing his hair up in braids, as was popular among Northsiders like Slim Thug, and shopping for bling at TV Jewelry. "He didn't look like the type of white dude you'd want to run up on," explains his former roommate, Vaughns.

Eventually, Riff Raff decided that being a rapper would be the most expedient way to achieve the celebrity he was after. He began absorbing the scene, doing his best to get noticed. "I always saw him around, at Swishahouse events or in the club parking lot," says the label's cofounder, producer OG Ron C. Many folks were put off by his look, OG Ron C adds, but his jolly personality won over others.

It was around this time that Horst began to develop his Southern street twang. "When he started to get into rap, he started to emulate the black culture," Ronald Simco says.

Vaughns adds, "Riff used to hang with only black people. When you hang with all black people, you talk black."

Around this time, in 2008, Riff Raff and Vaughns moved in together. Vaughns recalls that Riff Raff was, for a brief period, selling ecstasy pills. (Riff Raff did not respond to questions via his publicist concerning the allegations; asked in a radio interview if he'd ever sold drugs, he said he didn't want to "incriminate" himself.)

His raps were developing. As his confidence grew, he got sillier, donning girly, press-on nails for his early video "Juice." Riff Raff began making songs and videos with talent manager DB da Boss. Before long, his low-budget clips were gaining traction on YouTube and Worldstarhiphop. "He was very driven, very ambitious. You couldn't deny his work ethic," DB says. "Underneath that shell is a very intelligent man."

He acquired a pair of slick cars, according to Vaughns: a candy-green Sebring and a candy-pink Infinity. The latter's exterior had spinning rims and speakers so everyone could hear his music. But the coup de grâce was the trunk, which, when popped open, revealed glowing neon lights reading RIFF RAFF.

By then, Horst Simco had been fully absorbed into the Riff Raff character. He looked woefully out of place at his sister's 2008 wedding in Duluth; instead of a suit, he wore a short-sleeved, turquoise polo shirt and a black baseball cap over a do-rag. During the reception, he quietly freestyled in the back of the hall while someone toasted the bride and groom.

No one interviewed for this article professed to know much about Riff Raff's aspirations, about what was going on in his head. But his actions show a man determined to be famous.

In the late aughts, he wanted, badly, to get on television, even flying to Atlanta on his own dime to try out for From G's to Gents, a show purporting to smooth out the edges of rough street guys. When he learned that he'd made the second season's cast, before taping even began, he immediately got a giant MTV logo tattooed on his neck and started calling himself MTV Riff Raff.

He was quickly voted off by his fellow contestants. But viewers were intrigued by his funny ad-libs and fashion touches. The show was his first major forum, and he undertook a bit of mythmaking, claiming to be estranged from his father and saying he'd attended school for only 11 years. Ironically, despite the show's stated purpose, he was undertaking the opposite transformation, hoping to turn from a gent into a G.

Upon the show's debut in early 2009, the reaction was immediate. Suddenly he was getting tens of thousands of clicks on his MySpace profile. His name was spreading. Hipped to him by producer Alchemist, former MTV VJ and rapper Simon Rex called him. Before long, Riff Raff was visiting L.A. and sleeping on Rex's couch. The pair later formed a rap group called Three Loco with comedian Andy Milonakis.

In 2011, Riff Raff arrived in L.A. to stay. He won over critics via collaborations with hot artists such as Action Bronson, Chief Keef, Kitty Pryde, and Lil B, as well as solo tracks.

Last year, he surprised everyone by signing a deal with electro imprint Mad Decent. Its chief, superproducer Diplo, compared Riff Raff to early Apple stock — strong potential upside.

Riff Raff's brother, Viktor, is a vision of what Horst Simco might have become: He has a narrow, handsome face and a tall, athletic build, but his clean-cut look lacks easily visible tattoos. Horst also might have followed the path to graduate school, like his older sister, Amber, who has a pair of master's degrees.