It is a painting that bleeds history. Jean-Michel Basquiat’s Untitled (1982) portrays a black skull scarred with red rivulets, pitted with angry eyes, gnashing its teeth, against a blue graffiti wall on which someone has been doing their sums. Perhaps the street mathematician was calculating how many Africans died on slave ships in the 18th century, or how many people lived in slavery in America, or how many young black men have been killed by police guns in the last few years.

For there is a savage moral truth in the $110.5m paid for Basquiat’s skull at Sotheby’s in New York on Thursday that has made this searing expressionist painting the most expensive American artwork of all time.

Some serious critics – notably the late Robert Hughes, who dismissed Basquiat as a “featherweight” in an excoriation published just months after the 27-year-old painter’s death from heroin abuse in 1987 – might be rolling in their graves to see him anointed by market forces as the only American artist who belongs in the same financial company as Pablo Picasso.

Is Basquiat wilder than Jackson Pollock, more profound than Mark Rothko, more raw than Willem de Kooning? These are conventionally judged the greatest American painters, with Cy Twombly, Jasper Johns, Robert Rauschenberg and Andy Warhol close behind. The buyer is art collector Yusaku Maezawa, whose enthusiasm for Basquiat has singlehandedly driven his prices into outer space; he also set the previous record last year. Who is he to question the verdict of critics, museum collections and, up to now, auction houses about who the Great American Artists are?

Entrepreneur Yusaku Maezawa, the buyer of the Basquiat painting. Photograph: AP

He is, I suspect, a romantic. For this is actually a replay of the oldest story in modern culture. Ever since the English poet Thomas Chatterton died aged 17 in 1770 and was mourned as a romantic hero, the idea of the artist maudit, the dark and doomed genius, has created cults and made posthumous fortunes. Vincent van Gogh’s fame is inseparable from our image of his tormented life and premature death. Basquiat’s career was brief and spectacular, and cast in the romantic mould.

Today, in a world when art has become a form of mass entertainment, artistic celebrity and wealth are normal, and art dealers among the most sophisticated economic operators on the planet, it is easy to see why Maezawa is drawn to a man who even in his lifetime was already hailed by some as America’s Van Gogh.

Yet there’s another way to understand his passion for Basquiat, and a better reason to celebrate it. There’s a terrible clarity in Basquiat’s art. Like the work of another heroin user, William Burroughs, his art, with its feeling of being cut and hacked into the canvas rather than daubed, its electric sense of pain in every nerve, shows everyone what’s really in their lunch. He serves up American history with all the worms crawling out of it. This painting of a skull is not just about his own morbidity – it’s about being killed by America.

It did kill him, just as it has killed so many. Basquiat’s skull tells the same truth old blues songs do. It’s the skull of someone lynched. The skull of a slave. The skull of a death-row prisoner.

Sorry Bob – it looks like Basquiat really is a heavyweight after all. His art crawls with the ghosts of America’s racist and fatally cursed House of Usher.