Basquiat sold his first painting, Cadillac Moon (1981), to singer Debbie Harry, frontwoman of the punk rock band Blondie, for $200. They had filmed Downtown 81 together. Basquiat also appeared in the 1981 Blondie music video "Rapture," in a role originally intended for Grandmaster Flash, as a nightclub disc jockey. At the time, Basquiat was living with his girlfriend, Suzanne Mallouk, who financially supported him as a waitress. She later described his sexuality in Jennifer Clement's book, Widow Basquiat, as: "... not monochromatic. It did not rely on visual stimulation, such as a pretty girl. It was a very rich multichromatic sexuality. He was attracted to people for all different reasons. They could be boys, girls, thin, fat, pretty, ugly. It was, I think, driven by intelligence. He was attracted to intelligence more than anything and to pain."
In late 1981, Basquiat met Annina Nosei and participated in a group show called Public Address with Keith Haring and Barbara Kruger among others. He joined the Annina Nosei Gallery and worked in a basement below the gallery toward his first American one-man show in March 1982. Nosei provided him with a loft to live in which also served as a studio at 101 Crosby Street in SoHo. In March 1982, he painted in Modena for his second Italian exhibition. By that summer, he had left the Annina Nosei gallery and Bruno Bischofberger became his worldwide art dealer. In June 1982, Basquiat became the youngest artist to ever take part in Documenta in Kassel, Germany, where his works were exhibited alongside Joseph Beuys, Anselm Kiefer, Gerhard Richter, Cy Twombly, and Andy Warhol. Bischofberger gave Basquiat a one-man show in his Zurich gallery in September 1982. He arranged for Basquiat to meet Warhol for lunch on October 4, 1982. Warhol recalled that Basquiat "went home and within two hours a painting was back, still wet, of him and me together." The painting, Dos Cabezas (1982), ignited a friendship between them. Basquiat was photographed by James Van Der Zee for an interview with Henry Geldzahler published in the January 1983 issue of Warhol's Interview magazine. Starting in November 1982, Basquiat worked from the ground-floor display and studio space Larry Gagosian had built below his Venice, California home. There, he commenced a series of paintings for a March 1983 show; his second at the Gagosian Gallery in West Hollywood. Basquiat flew out his girlfriend, then-unknown singer Madonna, to accompany him. Gagosian recalled:
The first public showing of Basquiat's paintings and drawings was in 1981 at the MoMA PS1 New York/New Wave exhibit. The article in Artforum magazine entitled "Radiant Child" written by Rene Ricard after seeing the show brought Basquiat to the attention of the art world. In 1984, Basquiat immortalized Ricard in two drawings, Untitled (Axe/Rene) and Rene Ricard, representing the tension that existed between them.
Notable private collectors of Basquiat's work include David Bowie, Mera and Donald Rubell, Lars Ulrich, Steven A. Cohen, Laurence Graff, John McEnroe, Madonna, Debbie Harry, Leonardo DiCaprio, Swizz Beatz, Jay-Z, and Johnny Depp. Basquiat sold his first painting in 1981, and by 1982, spurred by the Neo-Expressionist art boom, his work was in great demand. Basquiat was on the cover of The New York Times Magazine in 1985 which was unprecedented for any young African-American artist. Since Basquiat's death in 1988, the market for his work has developed steadily—in line with overall art market trends—with a dramatic peak in 2007 when, at the height of the art market boom, the global auction volume for his work was over $115 million. Brett Gorvy, deputy chairman of Christie's, is quoted describing Basquiat's market as "two-tiered. ... The most coveted material is rare, generally dating from the best period, 1981–83."
Basquiat starred in Downtown 81, a vérité movie written by Glenn O'Brien and shot by Edo Bertoglio in 1981, but not released until 2000. In 1996, eight years after the artist's death, a biographical film titled Basquiat was released, directed by Julian Schnabel, with actor Jeffrey Wright starring as Basquiat. David Bowie played the part of Andy Warhol. Schnabel was interviewed during the film's script development as a personal acquaintance of Basquiat. Schnabel then purchased the rights to the project, believing that he could make a better film.