Madonna dated Jean-Michel Basquiat who gifted her some of his paintings during their relationship. Triggered by their break up, Basquiat took back and destroyed the paintings. However, she still owns at least one drawing of his. After an early set back in her pursuit for a desirable art collection, Madonna went on to acquire a number of notable works. She has a collection rumored to be worth over $100 million.

In 1987, she purchased Fernand Legér’s "Les Deux Bicyclettes" (1944). In 2013, Madonna sold another Legér, "Trois Femmes à la Table Rouge (Three Women at the Red Table)," at Sotheby’s for $7.2 million. She donated the proceeds to her own Ray of Light Foundation.

According to an interview with Vanity Fair, Madonna boasted her extensive collection of Tamara de Lempicka paintings: "I have a ton of her paintings in New York," she said. "I have a Lempicka museum."

Madonna has a few Frida Kahlo paintings including "Self Portrait with Monkey" (1940) and "My Birth (1932)." one of the five paintings created by the artist while she was living in Detroit. She also owns a Picasso, purchasing Picasso’s 'Buste de Femme à la Frange" (1938) for $5 million at Christie's in 2000.

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