Henry Fool is a 1997 American black comedy-drama film written, produced and directed by Hal Hartley, featuring Thomas Jay Ryan, James Urbaniak, and Parker Posey. As in The Unbelievable Truth, an earlier Hartley film, expectation and reality again conflict.
Socially inept garbage-man Simon Grim is befriended by Henry Fool, a witty rogue and untalented novelist. Henry opens the world of literature to Simon, and inspires him to write "the great American poem." Simon struggles to get his work recognized, and it is often dismissed as pornographic and scatological, but Henry continues to push and inspire Simon to get the poem published.
Henry carries around a bundle of notebooks that he refers to as his "Confession," a work that details aspects of his mysterious past that he one day hopes to publish, when he and the world is ready for them. Henry's hedonistic antics cause all manner of turns in the lives of Simon's family, not least of which is impregnating Fay, Simon's sister.
As Simon begins an ascent to the dizzying heights of Nobel Prize-winning poet, Henry sinks to a life of drinking in low-life bars as his own attempts at fame result in rejection, even by Simon's publisher who once employed Henry. The friends part ways and lose touch, until Henry’s criminal past catches up with him and he needs Simon’s help to flee the country.
Based on 28 reviews collected by the film review aggregator Rotten Tomatoes, 89% of critics gave Henry Fool a positive review, with an average rating of 7.4/10. Leonard Maltin gives the film two and a half stars, saying Hartley "just misses the mark".