A contrarian businessman with a penchant for fashion and boyish smile, the past decade saw rapper A$AP Rocky rise out of poverty in Harlem to become one of contemporary hip hop’s VIPs.

A$AP Rocky

Now the 30-year-old artist has found himself living in Swedish jail, as his alleged involvement in a street brawl has morphed from local incident to a case of global fascination.

Rocky is the de-facto leader of A$AP Mob — a New York-based hip hop collective of rappers, fashion designers, producers and music video directors — many of whom also use the A$AP moniker, an acronym that stands for “Always Strive and Prosper.”

Named Rakim Mayers in homage to half of the influential East Coast rap duo Eric B. & Rakim — his late sister was named Erika B. — the New York son began finding prominence after the viral success of videos for his singles “Peso” and “Purple Swag” on YouTube in the summer of 2011.

Shortly thereafter he dropped the mixtape “Live.Love.A$AP” to critical acclaim, pairing dazed soundscapes with a charismatic flow and taking on classic rap themes like promiscuity and drug use.

He triggered a bidding war among labels, eschewing commitment to any one place, finally signing in October 2011 a record deal with a label owned by Sony worth $3 million — $1.3 million of which went to his company A$AP Worldwide to support the collective.

“The plan is to not only release great music, culture, and style for myself and A$AP worldwide, but to also be the next major artist/exec in the business and make great businessmen out of my brothers,” he said at the time.

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In January 2013 he released his debut studio album, entitled “Long.Live.A$AP,” which jumped to the top of the Billboard charts. He has since released two more studio albums, most recently in 2018.

– ‘Pretty Flacko’ –
Despite his New York roots Rocky — a pescatarian who has extolled the creative benefits of LSD — has crafted a well-traveled sound, nodding to scenes from Houston to Atlanta to the Bay Area.

“I would not consider myself to be a quote unquote real New York rapper,” he told The New York Times in 2011. “I don’t even like New York rappers.”

Still, he did tell the Times he took pride in their approval: “It bring a tear to my eye to see native New York people give me my props because New York is stubborn and arrogant.”

The adolescent A$AP Rocky saw his father imprisoned and his brother shot dead. He began selling crack to get by, living for a time in a homeless shelter with his mother.

But from a young age he held that a key to success was developing a unique style musically but also in terms of fashion; he often describes cutting class in his teenage years to try and nab items from Manhattan luxury stores.

The rapper with a chiseled jawline sports box braids and refers to himself as “Pretty Flacko,” boasting of his looks, swagger and group orgies on the “gigantic” $100,000 bed he designed.

A master of the sharp flamboyance that’s long been tradition in Harlem, Rocky is partial to the Belgian designer Raf Simons, whom he saluted in the A$AP Mob song “Raf.”

“I don’t do fashion. I am fashion,” he told Esquire in 2018.

The rapper was working the European festival circuit and still had a slew of summer tour dates when he was arrested on July 3 along with three other people, following the brawl in Stockholm on June 30.

Prosecutors announced Thursday that he will be tried for assault next week over the fight, a decision likely to outrage legions of fans and fellow artists, some of whom have accused the Swedish justice system of racism over the case.

Even Donald Trump has weighed in on the case after urging from lifestyle mogul Kim Kardashian and rapper Kanye West, calling Sweden’s prime minister over Rocky’s plight.

The rapper has held that he acted in self-defence and faces a maximum penalty of two years in jail if convicted.

“The thing with me is if I feel disrespected I won’t hesitate to fight,” Rocky told British GQ in 2012. “But it takes a lot to make me feel disrespected.”

VANGUARD