Part One: Canon
The first, still the best, and one of the best horror films ever made - hell, one of the best genre films, any genre, ever made. It usually ranks fairly high on lists of horror fans and critics' lists, but I'm convinced the reason it doesn't rank higher is that, as explicated in the previous post, the frank psycho-sexual weirdness in the film makes a lot of people - even gorehound horror fans - extremely uncomfortable. The later films drop the sexual element almost entirely, or diminish it to the simple level of hetero titillation.
(I remember reading an interview - or was it a director's commentary? - with Tony Randall, director of Hellbound, who stated that during an early scene in the sequel where a mental patient flays himself with a straight razor, Executive Producer Clive Barker insisted they film an FX shot with the mental patient cutting off his penis. The director said something like, "well, that's just Clive". Well, no, that's Hellraiser in a nutshell: a psychotic man cutting off his cock with a straight edge razor on a bloody mattress.)
Considering that this film was made for a reported $1 million dollars, it's easily one of the best-looking "low budget" horror films ever made. Considering the Faustian bargain that Barker reportedly made in order to have the film made his way - signing over future franchise rights to New Line and agreeing to a paltry budget in exchange for the chance to direct his own book - the fact that it looks as good as it does is something of a minor miracle. Especially if you consider the fact that Barker was himself a novice filmmaker, with just two experimental shorts under his belt as a director. It's a shame, in a way, that he's not temperamentally suited to working in the film industry, because if he had chosen to focus his energies he probably could have been a director for the ages. As it is, he's probably a better writer, but still, the prose world's gain is film's loss. (And the first person to mention Lord of Illusions in the comments gets bopped on the head.)
It never loses its ability to shock and dismay.
Hellraiser II: Hellbound (1988)
A great sequel, almost as good as the original in some respects, but you can begin to discern how the wheels might come off in future installments.
A lot of people call this movie "cerebral", and I can see why - certainly, whereas the first film was almost exclusively focused on sexual metaphors, the second film is much more concerned with exploring the dark side of intellect. They spent a lot of time crafting some truly disturbing images, and they obviously had more money than the first film with which to do so. If you've ever been to a mental hospital - let alone been in a mental hospital - certain sections of this film are almost unwatchable. There's the aforementioned scene with the straight-razor, there's a lobotomy scene, there's a man getting a hand blender stuck on the end of demon phallus drilled into his skull . . . and then there's a scene in an elevator that is probably the single most horrifying sequence I've ever seen on film. It's not even that gristly a scene in the context of a movie where even the monsters get eviscerated and torn limb from limb, but I swear to God I almost never enter an elevator without thinking of the scene where Dr. Channard gets turned into a Cenobite. If you've seen it you know what I'm talking about.
But still, the movie suffers from an almost unintelligible third act. At a certain point you realize you have no idea why things are happening onscreen, and while they may be suitably gruesome and horrifying, you still don't understand why the man with the demon phallus thingie coming out of his head is killing everyone indiscriminately. A lot of its reputation for being "cerebral" comes, I think, simply from the fact that the plot is kind of vague in places, and it requires some thought to put all the proverbial pieces together. It's hard not to feel that just a little polishing on the script would have improved the final product inestimably.
Hellraiser III: Hell On Earth(1992)
And here's where it all falls apart.
If they had continued in the vein of the first two movies, the series would have devolved into some kind of unwatchable hybrid of Shinya Tsukamoto / early Cronenberg. But apparently the powers that be at New Line figured that the best way to continue actually, you know, making money with the franchise was to scale back the ambition and intellectual pretensions and make something more resembling a straight slasher film. And this is pretty much exactly what Hell On Earth is.
At least they try to give an in-movie explanation as to why Pinhead would go nuts and start spouting off sub-Freddy Krueger one-liners while dispatching bar-goers with floating CDs. But the problem is that instead of making a good Hellraiser film they decided to try and make a Pinhead film, and as I implied before the storytelling engine was just not designed to tell stories specifically about the monsters themselves. Getting to know Pinhead's "human" side and learning that he became Pinhead as a result of the grotesque charnal horror of the First World War - well, it's all rather besides the point, and it's all rather boring. At least, on a meta-level, there is some acknowledgment that turning the concept into a slash-by-numbers horror franchise essentially means bending it almost entirely out of recognition.
I've got an odd fondness for this film even if I also realize it's not very good. The first thing you need to know is that this is an "Alan Smithee" film. Kevin Yagher was the original director, and the cut he delivered to the studio was reportedly a half-hour longer than the finished film that was eventually cut to the bone and supplemented with post-production work by Joe Chappelle (who apparently later worked on The Wire). The extra half-hour of Yagher's cut was destroyed, Yagher subsequently took his name off the film, and the result was an awkward, defanged mess.
And yet, it's still kind of fun. The central idea is good: showing the history, not of Pinhead or Hell, but the puzzle box itself, by tracing the lineage of the man who unwittingly created the means by which Hell was able to begin its war on humanity. There are sequences in pre-Revolution 18th century France, contemporary America and, heh, the 22nd century in a floating space station. If you don't like horror in space, well, this probably isn't for you. (I mean, it's no Leprechaun 4: In Space, but what is?) Seeing the space marines (right out of Aliens, no less) take on the Cenobites is fun, even if - again - it deviates from the tone of the original films so dramatically that you can't imagine a Hannah Montana crossover would be much worse. There's even a cute Cenobite doggie - yes, a doggie.
Originally, the film was intended as more of an anthology, with a clear through-line from the French sequence all the way through the movie's concluding future sequence. The changes imposed after Yagher left the production resulted in the three plot threads being spliced together in a matter that could best be described as "haphazard". The ostensible reason for the changes was to keep the audiences from bristling at the lack of Pinhead until after the half-way point of the movie - but it's worth pointing out that Pinhead probably doesn't appear on screen in the first film for more than seven or eight minutes, tops. By this point, all the great thematics of the first two films have essentially been discarded: there's nothing too weird about hell anymore, it's just a slick vaguely Marylin Manson-ish place filled with evil demons who want to take over the earth. All of which has fuck all to do with the concept as introduced in The Hellbound Heart, but hey. You can sort of see the outlines of Yagher's attempt to hew closer to the spirit of the original film by introducing other denizens of Hell with conflicting goals from those of the Cenobites (a female demoness named Angelique), as an attempt to inject some mystery and sensuality back into the deracinated series. The mangled result ends up pretty predictable, but you can just barely discern the outlines of a superior film.
Turning Pinhead into the focal point of the mythos weakened the soup almost beyond recognition. He was never meant to be Freddy Krueger or Jason or even Hannibal Lector: he's scary because he's so mind-bogglingly weird and evil that you honestly can't conceive of anything worse than having him walk out of a glowing doorway and drag you to hell. Focusing the camera on him for any length of time ruins the mystique. Having devolved into just another slasher villain, he's a disappointment, just another cackling cinema boogieman to be easily dispatched in the space of 90 minutes. Bloodlines ends with a giant space station turning into a magic transformer and blasting Pinhead into smithereens with the power of the sun, or something - it might as well have been the Care Bear Scare. It's not very good but it gets points for style.