Free Enterprise (2000) is a film made by two trekkies about two trekkies about to enter their thirties and how they navigate their daily love lives and jobs with the hope of ascertaining happiness and fame. And who better to guide them than William Shatner playing a version of himself that no one had seen until then (going so far as to rap William Shakespeare’s Julius Caesar). The film follows the narrative style of Swingers but derives its greatest pleasure from the inherent elitism of its referential dialogue, which is so fast paced and obscure it could give the Gilmore Girls a run for their money. Yet, unlike most cult films, Free Enterprise is a heart felt romantic comedy, as unpretentious as it is obsessed with Captain Kirk of the U.S.S. Enterprise (fans of The Warriors and Streets Of Fire will recognize Debra Van Valkenburgh in a supporting role).
