'Fun' was, in fact, the prevalent mood on the Pumpkinhead set. Despite many additional burdens and responsibilities, Winston brought the same sense of humor and lighthearted spirit to directing Pumpkinhead as he had to his creature effects assignments. "Stan was a blast as a director," recalled Alec Gillis. "He was fun and completely relaxed on the set, as if he didn't have a care in the world. I remember one day when we were in this cramped cabin set, and I was very tense and tired because Shane and I had just spent three hours applying makeup to the actress playing the witch. But then I looked over and saw Stan standing across the room, staring at me, with his glasses cocked at a weird angle on his head -- just to make me laugh. There was my director, making an idiot of himself for nobody's benefit but mine. That isn't something most directors would do!"
Pumpkinhead has since become a cult classic since its release - among its fans, novelist Anne Rice, and many of the Stan Winston Studio crewmembers that worked on the show. "When I revisit Pumpkinhead after all these years," said Shane Mahan, "and I realize that it was done in 1987, all in-camera, and for only three million dollars, I'm amazed at how much movie is there. I think it is a really impressive example of a first-time director's work, and it is still used as a model for low-budget films. People reference Pumpkinhead all the time when they are looking at how to make an effective low-budget movie."
Originally, producers from the DeLaurentiis Entertainment Group (DEG), the film's production company, had sent Winston the script hoping to engage Stan Winston Studio to create the 'Pumpkinhead' demon, but Winston quickly recognized that, in Pumpkinhead, he had found an ideal property for his film-directing debut. "It was a small picture, something I thought I could handle as a director, and I felt there was a lot that I could bring to the story. So I told the producers, 'Yeah, I'll do the creature, but only if I can direct the movie.'"