I think this is my first proper headless horseman flick. Not just of this movie-a-day marathon - ever. I never saw the Depp one, and honestly, I think my most vibrant memory of the character is from an old Scooby-Doo episode (I think he's running with Scrappy and Scooby Dum in that one). Anyways, Curse of the Headless Horseman is not only a terrible introduction to the character, it's also a terrible movie, period. And oddly enough, it feels like a Scooby Doo episode at times - just with annoying drug addled hippies instead of... whatever Mystery Inc. was. Which sounds like it could be cool. But it's not.
It's about this doctor guy who inherits a ranch from his uncle. But there's a catch - if he can't turn it around and make it profitable in six months, the ownership of the property will go back to Solomon, the hilariously creepy caretaker. What is never mentioned (but you end up inferring) is that this isn't the kind of ranch where you raise cattle or anything - it's a tourist trap where they do annoying old-west style stage shows/recreations of gunfights or whatever. The doctor and his group of hippie friends clean the place up - you never see them do it but you assume that's the case, since that's what would normally happen in a narrative like this - and open it up for business.
But old cranky (and strangely gray-faced) Solomon is warning them that they can't possibly do this during the Talmud (I think) moon, because of some curse on the land or something. It's not entirely clear. The curse - shown in flashback that looks the exact same as the present day - began a hundred some years ago, and a headless horseman will return to get eight victims because... who knows? He's just a crazy, rambling old man anyways. And that's pretty much par for the course - nothing in The Curse of the Headless Horseman is well-explained.
Occasionally, one of the drugged-up hippies will wander out into the wilderness at (day for) night and encounter the headless horseman. He never does anything to them really - just kind of freaks them out and maybe splashes blood on them. Some curse! Anyways, since it's technically a movie someone has to figure out what is going on. Which they do, and it's really just a "meddling kids" speech away from a Scooby Doo reveal.
The first thing you notice about Curse is how terrible it looks and sounds. I'm sure the 50 Tales of Terror budget set transfer does the film no favors, but I don't know if this would ever be passable regardless of the source. The first 10-15 minutes have this strange red (or sometimes blue) hue, which makes me wonder if this was supposed to be 3D. Even once those colors go away, it looks muddy and cheap. And the sound is Bad News. If you are a fan of group scenes where a crowd just mumbles and talks over each other until everyone is inaudible, you'll love Curse of the Headless Horseman. I'd imagine much of this movie is what crowded public places sound like for people who have hearing aids. And the Foley work/sound mixing is terrible. There are several times where character's footsteps obscure their dialogue.
But the best technical production in the world couldn't have saved this one. Way too much of the film is just useless footage of faux-hippies doing faux-hippie stuff, including a horrible improv sketch that goes on and on, and more than one uncomfortable chase scene where a guy is chasing a woman that seems to end in a sexual assault. (Although later, he implies that "she's into it," so who knows...) And the horror aspects of the film are unintelligible. The horseman just kind of roams around with no particular goal, and when he happens to get close to someone, he douses them in blood... and that's it? Pretty weak. It says volumes about your film when the worst thing your titular villain can do is stain your shirt.
The only thing even close to redeeming about the film is Solomon, the eeeeeevil caretaker. He's kind of like this film's Torgo - just awkward and totally inept as a villain - but unfortunately he has very little screen time. He's pretty funny when he's spouting nonsense about the curse, and even though he looks like a slightly ashy guy with a scar on his face, just the sight of him causes more than one person to scream in pure terror.
Other than checking one off of the "watching everything on 50 Tales of Terror" list, there's no reason to watch Curse of the Headless Horseman. It's directionless, looks bad, and is really boring and crappy.
I would definitely avoid this film.
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