The two actors had first met during the making of Ron Howard’s Parenthood, in which Reeves co-starred with Phoenix’s then-girlfriend Martha Plimpton and his brother Joaquin (credited at the time as Leaf Phoenix). Reeves and Phoenix first shared the screen in Lawrence Kasdan’s I Love You to Death the following year. As the legend goes, Reeves took it upon himself to get the script for My Own Private Idaho to Phoenix, riding his motorcycle 1,300 miles from Canada to Florida to deliver it by hand. Phoenix eventually agreed to join Idaho—but on the condition that Reeves would sign on as well.

Unbeknownst to Van Sant, a pact had been forged between them: “We said, ‘OK, I’ll do it if you do it; I won’t do it if you don’t,’” Phoenix recounted to Interview in 1991. “We shook hands. That was it.” In the same interview, Reeves described feeling both daunted and excited by the project. “I was afraid,” he admitted. “But Gus and River made me fit in. Said, ‘Let’s do one bitchin’ movie.’”

With Phoenix and Reeves on board, Van Sant was finally able to secure financing and get Idaho off the ground, soon after commencing a shoot that was as loosely structured as his script. Van Sant’s sparsely written scenes left ample room for his performers—not only Phoenix and Reeves, but also the real-life hustlers he street-cast to play other members of Mike and Scott’s cadre—to set the tone through their own interpretations of the material. Although there was a good deal of Shakespearean verse to memorize, much of the film’s other dialogue was improvised by actors and incorporated into the script later on. “I don’t really care about the dialogue or even the action that’s written,” Van Sant explained to Tylevich. “I’d rather the actors be fluid. I give them a chance to think about who they are in the film. I want to see something new.”

One such inventive highlight in the film comes when Udo Kier—playing an eccentric European “john” in his first American film role—performs a jaunty musical number while holding a large floor lamp; Mike and Scott watch on in his hotel room, essentially a captive audience. Van Sant, who had admired Kier’s performances in 1970s underground films by Andy Warhol and Rainer Werner Fassbinder, lifted the idea for the scene from a real-life cabaret routine Kier performed in Germany using his own song, “Der Adler,” which Kier brought a recording of to the Idaho shoot.

The actor “had a lot of ideas,” Van Sant recalled in a 2016 Q&A, recounting the scene’s origins alongside Kier. Van Sant had asked him, “Why don’t you sing to the boys?” Kier recalled. “He gave me the big lamp; the technician had to make that long cable, and that’s what you see [in the film].” Kier was a prolific international star and took on hundreds of film and television roles across his 60-year career, before his death last year at the age of 81; when his passing was reported, many headlines cited Idaho as one of his most notable works.

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