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5. Burroughs: The Movie (dir. Howard Brookner, 1983) As Jones notes in his review, there are an array documentaries about Burroughs, but this is probably the most exhaustive, accurate, and honest feature-length investigation of the writer. The intimate moments captured here are often more unsettling and revealing than anything in David Cronenberg's Naked Lunch, itself a thorough albeit more fanciful examination of the writer's life and work.
4. Drugstore Cowboy (dir. Gus Van Sant, 1989) and Even Cowgirls Get the Blues (dir. Gus Van Sant, 1993) In their early work, Burroughs and Van Sant share multiple similarities, most notably their autobiographic treatment of drug addiction and sexuality. Burroughs's contributions to these films are minimal—he's credited with contributing additional dialogue to Drugstore Cowboy, the far superior of the two—but his almost ethereal presence illustrates Van Sant's respect and admiration for the writer. Bonuses: Van Sant's two short films, Thanksgiving Prayer, in which Burroughs recites his poem "Thanksgiving Day, Nov. 28, 1986," and The Discipline of D.E., based on the short story.
3. Chappaqua (dir. Conrad Rooks, 1966) Burroughs has a small role in this deeply weird cult item, playing a walking metaphor for heroin addiction (his character is not-so-subtly named Opium Jones.) Rooks shot the film periodically over three years, and when he became acquainted with Burroughs, Allen Ginsberg, Ravi Shankar, and other people associated with 60s counterculture, he worked them into his largely improvised film. The final product is a huge, totally fascinating mess. Burroughs had a tremendous influence on Rooks and how he directed, evident in the stylistic aberrations that punctuate the scenes in which he appears.
2. Towers Open Fire (dir. Anthony Balch/William S. Burroughs, 1963) The first film in which Burroughs, in collaboration with English filmmaker Anthony Balch, applied his cut-up technique to cinema. Following Dadaist poetry and constructivist film theory, Burroughs and Balch "cut up" and stringed together seemingly incongruous imagery to form a fragmented whole, a filmic representation of Burroughs's cut-up prose style. The film explores many of the same themes Burroughs was interested in during that time, but it isn't technically a "cut up" film, at least not in the formal sense. Really, it's a lead-up exercise to . . .
1. The Cut Ups (dir. Anthony Balch/William S. Burroughs, 1966) Conventionally shot and edited then chopped into foot-long intervals of four separate sequences, this experimental short follows an elaborate and mathematical structure to achieve a dissociative, lyrically radical visual montage. Like Burroughs's writing, this is foremost a narrative exercise, but one that considers the spatial and temporal significance of colliding imagery part of the "story." Formally, the film vaguely resembles something by Peter Kubelka, and it somewhat anticipates the American structuralist avant-garde film movement, but it also exists in its own little bubble, a one-off accomplishment that's pure Burroughs.