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Jean-Michel Basquiat, surrounded by his work in this 1985 file photo, ‘didn’t want to be a black artist. He wanted to be a famous artist,’ his friend, painter Arden Scott, has said.LIZZIE HIMMEL/The Associated Press

Dead at 27 in 1988 from a heroin overdose, Jean-Michel Basquiat would have been firmly ensconced in a deepening middle age today, had he lived. Where, then, might he be? Hanging at Soho Beach House in Miami, during Art Basel, gamely accepting acolytes and air-pecks? Part of the mix, possibly, at the annual Davos hang, fist-bumping with Elon Musk, Arianna Huffington and Shimon Peres? Quite conceivably he'd be May-Decembering with some fill-in-the-blank ingenue, or making the de rigueur cameo on HBO's Girls at the behest of Lena Dunham. His Instagram feed, no doubt, would be the hottest thing in smartphone-town.

An alternate reality might, however, just as likely relegate the artist to the moment-in-time fringes of a 1980s-lit SoHo, his rendezvous with history marred by the fact that he didn't … well … expire. Dubbed by some now as the art world's Charlie Parker, and the posthumous hand behind mind-boggling auction prices (such as the $48.8-million his Dustheads painting fetched at Christie's in 2013), Basquiat remains blithely, tragically frozen in time.

Death quite often being the canniest career move, as both the Princess of Wales and James Dean will attest, and the so-called "27 Club" being a potent one – see: Joplin, Morrison, Cobain et al. – Basquiat, the man, and Basquiat, the myth, blurred long, long ago. And Basquiatiana, as it were, rumbles steadily down the nostalgia chute, currently exemplified by a massive new retrospective of his work opening Saturday at Toronto's Art Gallery of Ontario. The work endures because the work endures, it's true. But add extreme celebrity to the mix – a role that Basquiat coveted, and method-acted to the hilt in some ways – and the oeuvre is inextricably linked to his personal narrative, a virtual kaleidoscope for looking at matters of race, dollars and fame. It's a legacy as paint-splattered as the iconic Armani suits he used to trawl around town in. Dating Madonna, at the height of her Lucky Star era. Hanging with his spiritual papa, Andy Warhol, inside the creamy hot spot environs of Mr. Chow. Beautiful and barefoot on the cover of The New York Times Magazine, his rebel gaze looking out over a headline that read: "New Art, New Money: The Marketing of an American Artist." As far as zeniths go, Basquiat got his.

So, money. Coinciding with Basquiat's rise was a quake in the art market – moolah, lots of it. As his biographer Phoebe Hoban has noted, the Bonfire of the Vanities era "engendered an interesting offspring: SoHo's bull market," with the new money of the eighties increasingly funnelled into art. "By 1983," she writes, "the art market in Manhattan alone was estimated at $2-billion … gallery dealers became power players, barely distinguishable in lingo and lifestyle from their Wall Street clientele … chauffeured cars disgorged fur-coated women into tiny storefront galleries in the bowels of the East Village." Right place, right time, i.e., for a certain dreadlocked virtuoso, who'd entered, stage left, as an anonymous graffiti artist, his work initially only signed "SAMO" all over New York.

The art boom created a crop of careerist-artists, à la Julian Schnabel and Francesco Clemente, and an art-as-fashion trope that's so entrenched on this side of the millennium that it barely needs pointing out.

The "black-ness" of Basquiat didn't exactly hurt in this changing landscape when hip hop was just taking off, or, as the late, great art critic Robert Hughes once pointed out archly, "collectors were ready for a wild child, a curiosity, an urban noble savage." It was, he went on, "the racist idea of the black as naif or as rhythmic innocent, and to the idea of the black artist as 'instinctual,' outside 'mainstream' culture … a wild pet for the recently cultivated white." Knowingly or not, it's a role happily slipped into by Basquiat who – though he'd lived on the street for a bit – was, in fact, "an upper-middle-class private-school boy of Haitian parentage … whose father drove a Mercedes."

In the United States's current bipolar culture – one of both the Ferguson riots and a black President in the White House – it's worth looking at things through the Basquiat lens. While his paintings made powerful references to black history and black icons, and some of it was downright political – the new show at the AGO, for instance, features Irony of a Negro Policeman (1981), a sturdy critique of racial injustice and police brutality in 1980s New York – Basquiat had a complicated relationship with race. His friend, the painter Arden Scott, has recalled, "He didn't want to be a black artist. He wanted to be a famous artist."

Like many in the post-Martin Luther King era, Basquiat straddled two worlds, as many have noted. He never experienced racial segregation, though he did suffer the indignity of not being able to get taxis to stop for him. Moreover, as Hoban has noted, he had few black friends, fewer black peers and was not exactly embraced by African-American critics in his lifetime. Like his father, too, he rarely dated black women.

Which, perhaps, brings us to Madonna. When Basquiat dated her she wasn't quite "Madonna." But in the decades since his death, his supernova status has only been boosted by his connection to her. As recently as last year, she was being asked about the romance in an interview in W magazine, in which the Material Girl spoke fondly of their wordless reverie.

"I remember getting up in the middle of the night and he wouldn't be in bed lying next to me," she recalled, "he'd be standing, painting, at 4 in the morning, this close to the canvas, in a trance."

Star light, star bright. The myth chugs on.

Jean-Michel Basquiat: Now's the Time runs at the Art Gallery of Ontario in Toronto from Feb. 7 to May 10 (ago.net).