The film opens with Jean (portrayed by Basquiat) hospitalized for an undisclosed ailment. Upon discharge, he encounters an enigmatic woman named Beatrice (played by Anna Schroeder) who offers him a ride in her convertible. Returning to his apartment, Jean learns that his landlord, portrayed by former Yardbirds manager Giorgio Gomelsky, is evicting him.
As Jean tries to sell his artwork, he encounters various characters from the downtown New York scene, including musician Arto Lindsay, graffiti artists Lee Quiñones and Fab Five Freddy, and others. Despite his struggles, Jean manages to sell some of his art to a wealthy middle-aged woman. Throughout the film, he wanders the streets of New York City in search of Beatrice, encountering performances by Kid Creole and the Coconuts and James White and the Blacks. Eventually, he encounters a bag lady portrayed by Debbie Harry, who transforms into a princess after Jean kisses her and rewards him with a stack of cash.
"Downtown 81" is more than just a film; it's a time machine transporting viewers back to the vibrant cultural scene of early 1980s New York. Basquiat's rising fame adds to the film's allure, but its real charm lies in its portrayal of the music scene and its influential but lesser-known bands. Despite some technical challenges, including post-production issues that led to dubbed dialogue, the film captures the essence of a bygone era and the exaggerated personalities that populated it. As Jean navigates through various urban settings, from affluent art patron homes to post-apocalyptic neighborhoods, viewers are immersed in the world of downtown New York, complete with its iconic venues like the Mudd Club.
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