There was a time when Hal Hartley was considered the golden boy of American independent cinema. With movies such as Trust and Amateur, Hartley had demonstrated a gift for casting a wry, sardonic glance on American society, populating his movies with eccentric outcasts and loners trapped in never ending existential loops from which they struggled to escape. Henry Fool is another Hal Hartley classic which mixes cod-philosophy with deadbeat losers; the tale of the titular aspiring novelist, certain of his own greatness, where the real world never quite lives up to expectations. When Henry (played by Thomas Jay Ryan) befriends Simon Grim (James Urbaniak) he insinuates his way into his family, impregnating Simon's sister Fay (Parker Posey). After lording over Simon with his misguided sense of superiority, Henry sinks into an alcohol-fueled depression, watching from the sidelines as Simon finds increasing success as a poet. As deadpan as the best of Hartley's great films, Henry Fool is a great low-key exploration of the pitfalls of writing and the hubris and delusions which lead to an aspiring writer's downfall. Occasionally pretentious and shot through with a streak of deadpan humour, it's one of the great American independents of the 1990s.
