A SURVEY of African American art is about the last place you'd expect to hear about Madonna, but that's nonetheless what happened when I sat down in a basement classroom at the University of Washington the summer after my sophomore year of college. A bureaucratic hiccup over study-abroad requirements had landed me in voluntary summer school, but the result was something much more important: a disruption in my up-to-that-point very white, very canonical art historical education that arrived in the form of Haitian American artist Jean-Michel Basquiat.

Against my professor's advice, I tore through Phoebe Hoban's Basquiat: A Quick Killing in Art, a gossipy, fluffy account of the artist's rise to prominence in the New York art scene of the '80s—and the perfect antidote to the dry criticism I was used to. Everything about Basquiat is interesting, from his indignant, unapologetic responses to racist interviewers to his contentious relationship with Andy Warhol to, most of all, his graffiti-derived paintings. And then there was Madonna, his girlfriend at the time, a dancer and aspiring singer who Hoban takes pains to say wasn't famous yet, and didn't share Basquiat's appetite for self-destruction. While he sank into the heroin addiction that would eventually kill him at 27, Madonna, then anonymous, was an early adopter of fitness and carrot sticks.

I find this civilian vegetable-enthusiast Madonna infinitely more fascinating than the one who would emerge later that decade with her synthesizer-heavy songs and her crucifix—and certainly more so than her later incarnations, who increasingly read as facsimiles of younger artists (Lady Gaga, Britney Spears) who are themselves facsimiles of Madonna. I imagine this pre-fame Madonna as one of many aspiring modern-dance art babies who surely populated the New York art world, arriving as she did from Michigan, with $35 in her pocket (by her own admission), her eyebrows still dark and Gandalf-y and fierce. Here is a baby-faced Madonna in a leather jacket, with a comically large bow in her hair, seemingly disinterested in the camera, a woman whose career could have taken an entirely different trajectory altogether—Madonna as Warhol Factory girl, Madonna as rough-edged downtown punk, Madonna as poet, Madonna as conceptual artist.

But of course, that's not what happened. Madonna became a pop star, and with that her NYC art scene days were relegated to trashy art history books, her high-profile relationships with celebrities like (alleged abusive douchebag) Sean Penn and Warren Beatty supplanting Basquiat in her mythology.

When Madonna talks about Basquiat today, it reads more as shorthand for cool, a grab for art-world legitimacy, than genuine recollection of something that actually happened to her, someone she once knew. When Madonna references Basquiat now in an Instagram post promoting her new album, black rope Photoshopped onto his face, it makes me cringe. It looks appropriative. There's no denying that, like Basquiat, Madonna is an American icon for a reason, and that's perhaps why it seems so desperate and strange of her to use his image to sell what is essentially a copy of a copy of a copy of the thing it once seemed only she knew how to do.

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