When Jean-Michel Basquiat was 19, he moved into a crumbling Manhattan apartment with his then-girlfriend, Alexis Adler. There, she remembers, “music was playing all the time.” Music was a source of creative inspiration for Basquiat, whose work often depicted musical motifs like jazz artists and brass instruments. Before his early death at age 27, the street artist also designed the album covers for two vinyl records. The first design was for Beat Bop, a 1983 rap battle between the graffiti artists-turned-MCs K-Roband Rammellzee. Basquiat financed and produced the track on his own music label, Tartown Inc. As the legend goes, Basquiat himself charged into the recording booth during the heated session—though his lyrics didn’t make the cut on the final record. Basquiat’s next design, a 1984 cover for the San Francisco punk band, The Offs, depicts a single figure in Basquiat’s traditional cartoonish style and childish script. Though the album didn’t sell well at the time, Basquiat’s iconic cover design has made it one of the most expensive records of all time.