He certainly sounded new. Released in the fall of 2011, his first mixtape LIVE.LOVE.A$AP’s fusion of Memphis and Houston-indebted flows, spaced-out cloud rap production, and distinctly uptown swag was like a shot of adrenaline into the New York rap world’s heart. “Peso,” the single that would land Rocky on Hot 97’s hallowed airwaves for the first time, played like a compilation of all of regional rap’s best impulses: There were syncopated sprinkles of Bone Thugs, syrupy splashes of Pimp C, and the slick bravado of JAY-Z’s ’90s New York. At times a woozy, smoke-filled kickback and at others a raucous warehouse party, it was, as Jon Caramanica wrote in The New York Times, “deeply assured and heavily narcotic,” the rare instance where an artist emerged fully formed with their own unique look and sound.

The answer seems to lie, at least partially, in the company Rocky keeps. Over the years, he has collaborated with seemingly everyone. He’s dueted with Lana Del Rey, partnered extensively with British cult figure Dean Blunt, penned party anthems with Kendrick Lamar, and boosted cars with FKA twigs. He possesses aesthetic versatility shared by few others. This chameleonic quality, consummate charm, and creative polyglotism have helped endear him to audiences that extend far beyond the world of New York City hip hop. How many people on this planet can just as easily chop it up with N.O.R.E. on Drink Champs as they can cozy up with Michèle Lamy at Paris Fashion Week?

We simply do not have enough space in this article to name all the collaborations Rocky has been a part of in the last decade (“Everything that I am working on excites me — or I wouldn’t be doing it!”), but here are just a few: a sneaker with Under Armour, a capsule collection with cutting edge French designer Marine Serre (partially designed while behind bars in Sweden), a signature pair of Vans, an appointment as PacSun’s guest artistic director, and a collaboration with Mercedes-Benz. “The industry is always evolving, and changes give opportunities to different ideas. I think it is important to try to embrace the newness and the ever-changing world,” Rocky says of his multidisciplinary engagements. In the last two years alone, he started a new whisky brand, Mercer + Prince, directed a commercial for Beats, and was recently named the creative director of Puma’s joint venture with Formula 1. This last post was more unexpected and in a space that he describes as being “very traditional.” He’s hoping to “shake the room up a bit.”

That’s all before we even get to the music.

The pair lounge on a fire escape in Timberland boots and sorbet-toned furs; Rocky retrieves Rihanna at the hair salon in a studded Manchester United kit; Rihanna struts down the block in a knitted bikini top as neighborhood kids help her with the groceries. It’s a kaleidoscopic montage of coupled city bliss. In the video’s most poignant moment, the pair are wed in the hallway of a humble apartment complex. They lock eyes and he smiles, revealing a gleaming pair of custom fronts that say “MARRY ME?” She smiles in turn, a jewel-encrusted “I DO” capping her left canine.

Rocky doesn’t see himself leaving the spotlight anytime soon. “I think while I’m still here, I got a duty to aspire to inspire,” he says. He still considers himself top of his class.

“There’s really only a few people who control the culture, and when I tell you that I’m at the forefront, believe dat!”

Head here to get a copy of the new issue of Highsnobiety Magazine.