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.

Set like previous Hartley films in less affluent parts of Long Island, it recounts how the lives of a fatherless family are overturned by a mysterious outsider and how, as in The Unbelievable Truth, expectation and reality again conflict.

Socially inept garbageman Simon Grim lives a monotonous life with his sister Fay, unemployed, and his mother Mary, who suffers from severe depression.

Henry Fool, who's on probation from prison for statutory rape, sets himself up in their basement and proceeds to impinge himself on their daily lives.

Simon fills several notebooks with what turns out to be a poem and Henry encourages him to try to get it published, even though it is dismissed by many as pornographic and scatological.

Henry himself has a number of notebooks that he refers to as his Confession, a work that details his mysterious past and which he hopes to publish, although he won't let anyone read them.

Excited by the opportunity to profit from the poem, Angus approaches Simon again and, after negotiations, ultimately offers him $200,000 up front and a 60/40 royalty split to publish it.

Henry is distressed over becoming a father, worried that the time spent working a job to support his family will conflict with his passions as a writer.

Simon was supposed to be on his way to the airport to catch a flight to Stockholm to accept his Nobel Prize, but instead has his passport altered and gives it and his ticket to Henry.

They arrive late for the flight but, due to Simon's prestige and mission, the airline holds the plane as a courtesy.

[4] Hartley wanted the story to incorporate current events, adding elements such as Congressional races and Internet censorship.

[8] Henry Fool marked the feature film debuts of Thomas Jay Ryan,[4][9] James Urbaniak,[10] and Liam Aiken.

[6] The start of filming was delayed several times because of financial setbacks, and Ryan had a year and a half to discuss his character with Hartley.