Writer/director Gus Van Sant is thought of as maverick film artist by the Hollywood community and his films are a badge of honor to the young actors who appear in them. Since the critical success of the quirky "Drugstore Cowboy", which had a strong element of heterosexual romance, and the depraved "My Own Private Idaho", which had a strong element of homosexual romance, Van Sant has turned his attention towards the remaining sexual preference. "Even Cowgirls Get the Blues" seems to be about, more than anything else, the awakening of lesbian feelings in its main character. As such, the film will likely have little appeal to mainstream audiences.
Sissy Hankshaw (Uma Thurman) was born with thumbs twice the size of those usually found on an otherwise normal person. Using these to her advantage, Sissy delights in being the best hitch-hiker the world has ever known. She travels constantly because she feels that that is what she was put on earth to do. One day her drag queen friend, the Countess (John Hurt), sets her up with a young artist (Keanu Reeves). Sissy discovers that her sexuality is not non-existent, rather that it has been suppressed as part of her lifestyle.
As part of her awakening, Sissy is sent to the Rubber Rose Ranch, a retreat owned by the Countess which serves as a live-in beauty clinic. The ranch also is home to a herd of cows, for atmosphere, which has been drawing an unwanted element, namely cowgirls. Such women are staunchly feminist, but are more than a shade less refined than the ranch's normal clientele. As a matter of fact, the Countess would like nothing more than to have the lot of them removed. When the attempt is made, the cowgirls strike back and take possession of the ranch. From there they begin a siege against the federal officers who claim they are holding captive a flock of rare whooping cranes. Meanwhile, Sissy becomes romantically involved with the leader of the cowgirls, Bonanza Jellybean (Rain Phoenix).
As ridiculous as this set-up sounds, the film as a whole is even more so. "Even Cowgirls Get the Blues" is presented in a stylized way, disguising what might otherwise appear to be a rampant lack of acting talent in its cast. The young and the hip tend to look at Gus Van Sant as a minor deity, courageously tackling frontiers taboo to other filmmakers. But this film, and his previous one, are indicative of the fact that his reputation doesn't come from his ability to entertain as much as from his outlaw image.