Hal Hartley follows 1995's pleasant but insubstantial Flirt with his biggest and most ambitious film to date. Henry Fool tells the story of an ex-con (Thomas Jay Ryan) who, upon his release from prison, enters and immediately transforms the lives of a poetry-writing garbage man (James Urbaniak), his bitchy, nymphomaniacal sister (Parker Posey), and their morbidly depressed mother. Ryan fancies himself a sort of modern-day Henry Miller, but in his relationship to Urbaniak, he functions more as a corrupt, over-the-hill Neal Cassady to Urbaniak's introverted, exponentially more gifted Jack Kerouac. Like most of Hartley's films, Henry Fool tells the story of socially ostracized outsiders and the bonds they form to escape the bleak, despairing misery of their day-to-day existence. But Henry Fool is more than just a story about outsiders: It's also a meditation on the relationship between art and fame in American society, a satire about the myth of the starving artist, and an examination of the boundaries of friendship and the possibility of redemption. Ryan's charismatic, deluded outsider has his fair share of literary and cinematic precedents—most obviously the outsider antiheroes of some of Hartley's other films and the protagonist in John Kennedy Toole's A Confederacy Of Dunces—but Ryan makes the role wholly his own. His title character is a towering comic creation, a man who is morally reprehensible yet oddly appealing, pathetic yet undeniably vital, and Ryan is able to deliver even the most stilted of Hartley's lines with a rhythmic grace that carries the film through its occasional rough spots. Ryan is more than matched by the rest of the universally fine cast, most notably Urbaniak, who is believable playing a similarly idiosyncratic character, and Posey, who does wonders with a seemingly thankless role.