What It’s About: Jamie Benjamin (Sammy Snyders) is the strange kid that no one likes. In a normal film, we’d learn of Jamie’s special talent that eventually wins the heart of his community, or perhaps he’d meet a nice strange girl and the pair would escape small town mediocrity together, or perhaps something unusual would happen and Jamie would be forced to come out of his shell. We might even learn that there is some problem in his home life motivating his odd behavior.
The Pit, however, is most definitely not a normal movie; it is the product of what El Santo of 1,000 Misspent Hours and Counting calls “wrong thinking”. What we learn instead is that Jamie is a voyeur and pervert capable of using phony claims of kidnapping to force his librarian neighbor to strip in her window while he takes pictures. A normal film would stop there, but The Pit is not normal. Providing counsel to Jamie is his teddy bear, Teddy. Teddy talks to Jamie and encourages him in his bad behavior. An insane, perverted, and mentally damaged kid and his possibly possessed teddy bear Teddy; that’s enough for one movie, right? Well, maybe for your average movie, yes, but not for The Pit. No, The Pit throws in a pit full of little creatures called Tra-la-logs who Jamie feeds people he doesn’t like. This is truly a one of a kind film.
Why Watch it Today?: Teddy Roosevelt famously refused to shoot a bear cub today in 1902, lending his name to stuffed toy bears forever after. Of all the films to feature a teddy bear, The Pit is the strangest, though if you can challenge my judgement on that score, my fall back position is “of all the films that feature talking teddy bears that encourage their child owners to engage in voyeuristic behavior, The Pit is the strangest.” Fans of cult films and oddities owe themselves a viewing of this bizarre Canadian film, which gives just enough contradictory hints of writer Ian Stuart’s original script to allow the viewer to see past the changes director/producer Lew Lehman made in an attempt to make a more commercial horror film. If anything, the conflict between these two visions makes The Pit more interesting than it would be if either man had gotten their way.
The whole film is available on YouTube:
The League of Dead Films 
I so wanna see this now. And, great tie-in to the calendar date. That interview you linked is also fascinating. “You wrote a great script, Ian, and we turned it into just another Grade “B” movie.”
Look forward to hearing what you think about it Sig. I found that interview researching this entry and it amazed me…really helped me understand what the hell was up with the film.