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The title of the film was taken from the East Hampton neighborhood of Maidstone. According to a July 1968 New York Times article, the picture was filmed in the following East Hampton, NY locations: the summer house of Grove Press editor Barney Rosset, a mansion owned by artist Alfonso Ossorio, the David Brockman estate and at the estate of Robert David Lion Gardiner on Gardiner's Island. According to the July 1968 New York Times article, there were five film crews, one of which was led by Rip Torn. The cast consisted of over 100 of director-writer Norman Mailer's friends and acquaintances, including several of Mailer's ex-wives, playwrights Jack Richardson and Michael McClure, former light-heavyweight boxing champion Jos Torres and Torn, the only prominent professional actor in the cast.
Mailer, a noted novelist, nonfiction writer, essayist and screenwriter, conceived the film as a multilevel improvisation, which, according to Mailer as quoted in an Esquire article, would be about "beauty, intrigue, and the subtle nature of reality...how difficult it is to know what reality is until you take it through its paces." In the Variety review, Mailer was quoted as stating that because reality cannot be captured by a definite storyline, he would allow his actors to improvise on the original premise of the film.
After filming was completed, Mailer spent two years editing down the 45 hours of footage to 110 minutes. According to the Variety review, the completed film was broken down into fourteen chapter headings in which documentary footage of making the movie was intercut with the film itself. One of the most controversial sequences in the film was a scene in which Torn, whose role is "Raoul Rey O'Houlihan," the jealous half-brother of Mailer's character, "Norman T. Kingsley," smashed Mailer over the head with a small hammer in front of Mailer's wife and children. In retaliation, Mailer bit open Torn's ear. The nature between fiction and reality is blurred because Torn claimed he was actually assaulting the character of Kingsley, in an attempt to validate the film. A transcription of the screenplay was later published in paperback by Signet. Mailer did not direct another film until 1987.