After the success of Drugstore Cowboys, the studios courted Van Sant with lucrative offers, but he resisted the mainstream lure and was rewarded with critical and popular acclaim for his next film, My Own Private Idaho.
A retelling of Shakespeare's Henry V, set among street hustlers, My Own Private Idaho is by turns nonchalant, touching and angry, graced with unexpected images and narrative hairpins. Having teenage hustlers lapse into Shakespearean verse doesn't always work but it suits the story. More problematic for mainstream viewers is the film's veering off the narrative track, which was like a pileup of open parentheses within parentheses that never get satisfactorily closed.
The center of the story is Mike Waters (River Phoenix), a narcoleptic hustler, desperately searching for the mother who abandoned him as a child. Mike falls in love with Scott Favor (Keanu Reeves), a fellow hustler, who stands to inherit a fortune from his father, Portland's paraplegic mayor. Scott looks upon Bob Pigeon (William Richert), a cocaine-dealing braggart–and the film's Falstaff–as his “true father.” As the Prince Hal figure, Scott intends to renounce his carefree streetlife and repudiate his friends when his father dies.
For his modern, skid-row reworking of Shakespeare, Van Sant was inspired by Orson Welles's 1966 film, Chimes at Midnight, which is based pn Shakspeare's Henry IV, with Welles in the Falstaff role.
The end result is an uneven, though lyrically shot film, that for some critics reads like an expanded version of Van Sant's earlier films, only elevating their issues to a more poetic and universal level.
Once again, Van Sant courted controversy in his treatment of the homoerotic exploits of male hustlers. Characteristically, however, he ignored warnings that male prostitution and homosexuality were taboos in a social climate marked by hysteria over the AIDS epidemic.