Take for example, Basquiat, whom Madonna dated in the early ’80s, when they were both on the brink of fame. Now one of the most popular artists on the market, Basquiat died in 1988, at just 28 years old, meaning that there’s only so much of his work out there to be bought and put on display (which is partly why his work continues to break records at auction). And, as Madonna revealed to Howard Stern in 2015, there’s even less of it because of his reaction to their breakup in 1984.
Since it wasn’t out of the ordinary for Madonna to wake up in the middle of the night and find that Basquiat wasn’t lying in bed but was on his feet painting, it’s only natural that over the course of a couple of years Madonna came to own quite a few pieces of Basquiat’s art. Those, however, will never be seen. 'When I broke up with him, he made me give [the paintings he gave me] back to him, and then he painted over them black,' she told Stern.
It’s unclear just how many Basquiats we lost to spite - Madonna was hardly the only notable woman he dated, although certainly the most notable - but we do know there’s only a single Frida Kahlo that Madonna has been keeping from the public eye, thankfully. Unfortunately, it happens to be arguably one of the most amazing works Kahlo ever produced. Painted in 1932, My Birth is true to its title: It’s a self-portrait, but Kahlo’s head isn’t in its usual place, atop her shoulders - instead, it is in the process of emerging from the womb. It’s quite a sight to see, and quite a privilege to see it, given that Madonna turned down the Detroit Institute of Arts’ many pleas to feature it in a 2015 exhibition of the works that Kahlo made while she and Diego Rivera lived in Detroit. ('You have no idea what we went through,' the institute’s adjunct curator said at the time.)
Madonna had, in fact, loaned the painting to the Tate back in 2005, and wouldn’t have exactly been artless without it; as Vanity Fair reported in 1990, back then, at least, she also owned works by Diego Rivera, Man Ray, Weegee, Tina Modotti, Herb Ritts, and even Fernand Léger. To be fair, her appreciation for the work seems to be the reason behind her unwillingness to share it: 'If somebody doesn’t like this painting,' Madonna told the magazine, 'then I know they can’t be my friend.'
For all the great art Madonna has effectively kept from us, she’s also gone out of her way to bring art to the mainstream - not exactly surprising, given that she’s a fan of artists like Banksy and JR, who remind her of Basquiat and Haring. 'You can see Banksy’s work driving by it on the street, and JR’s work - the way he takes photographs of people and turns them into heroes in their communities and makes people proud of who they are,' she told David Blaine in 2014, adding that her son was even interning for JR.
Madonna has brought art to the streets herself in a way too, like when she used the video Green Pink Caviar by the provocative New York–based artist Marilyn Minter, with whom she’s friends, as the backdrop for a portion of her Sticky and Sweet tour, preceding its stint as part of a public art project in Los Angeles. More recently, Madonna also fundraised for her nonprofit Raising Malawi by launching a contest that would give two 'art world virgins' the chance to accompany her to Art Basel Miami Beach for an ultra-exclusive, up-close look at a plethora of blue chip art (and, as it turned out, at her twerking with Ariana Grande, which has likely only appreciated in market value since).
From W Magazine