/Film Showdown: Leatherface Vs. Pinhead
Two souls enter. One soul gets torn apart.
Clive Barker's novella "The Hellbound Heart" was first published in 1986 and adapted to film as "Hellraiser" in 1987 by Barker himself. In it, a man solves a mysterious supernatural puzzle box which summons an immortal order of demonic sadomasochists from beyond the grave. They force upon him the ultimate sensual experience, wherein pain and pleasure become inseparable. In the original story, the leader of these demons, called Cenobites, was a young woman with decorative nails hammered partway into her skull, with the idea being that the Cenobites are simultaneously in a constant state of extreme pain and extreme pleasure. It's BDSM horror at its finest. In the film, the lead Cenobite was altered into a male character played by Doug Bradley. It wouldn't be until the 1989 sequel "Hellbound: Hellraiser II" that the character would be nicknamed Pinhead.
Tobe Hooper's 1974 classic "The Texas Chain Saw Massacre" was not based on a novel, and its events are 100% fictional, but it was inspired partly by the real-life murders of notorious serial killer Ed Gein, who murdered multiple people in the late 1950s in Plainfield, Wisconsin. Gein was not only guilty of murder, but confessed to multiple instances of grave robbery. His house was full of grisly craft projects extrapolated from the skin and bones of the bodies he dug up. Those details captured the imagination of Hooper and his co-screenwriter Kim Henkel, and they came up with a story of a group of young people finding a remote home in Texas populated by a mad clan of cannibals. The near-mute "child" of the family was nicknamed Leatherface because of the mask of human skin he wore. Leatherface was a simple butcher, and had dismemberment down to a science.
So we have two ghouls interested in flesh, two characters expert in rending human bodies, two characters skilled in the use of meathooks. The time has come to compare Pinhead and Leatherface, and pit them against one another in fictional combat.
Their motivations for fighting
Let's imagine the scenario wherein these two titans would meet: Bubba Sawyer/Thomas Brown Hewitt/Jedidiah Sawyer, aka Leatherface, is a good ol' inbred Texas mutant, and Pinhead is a supernatural S&M Cenobite from Hell. There's no world in which these two are going to randomly encounter one another, especially when Pinhead can only be summoned by unlocking the Lament Configuration, which Leatherface is likely not clever enough to do on his own. For the sake of argument, let's defy all movie logic and assume that some unsuspecting Texas teen pulls a Kristy Cotton and figures out the puzzle box while hanging out alone in a barn, just before Bubba slices and dices them into tiny pieces to turn into barbecue meat. Now, Leatherface stands alone in a barn, surrounded by the remains of a disembodied teen, as the Lament Configuration unlocks, transforming the barn walls into a dimensional door and allowing Leatherface to encounter the Cenobites.
Defeating Pinhead would require Leatherface to reconfigure the box and reverse the solution, which is something he is simply incapable of achieving. Upon first sight of Pinhead, Leatherface fully freaks out, putting his chainsaw between the two of them like a lion tamer with a stool and whip. Pinhead is unfazed by Leatherface's threats, which is the complete opposite of what Bubba is used to. Pinhead's fearless confidence confuses Leatherface, and as Pinhead dives into a sexy, scary monologue about his horrific powers and intentions on killing the Sawyer family, Leatherface interrupts Pinhead by grabbing him and placing him atop the meat hook hanging in the corner of the barn, similar to Pam in "The Texas Chain Saw Massacre." Pinhead wails in pain and ecstasy, clearly loving the pain Leatherface has inflicted upon him.
This has turned into something else entirely
Because Pinhead lives by the edict that pain and pleasure are indivisible, being speared on a meat hook is a pleasant experience. He may have a large puncture in his lung, but this is a supernatural S&M deity from beyond the grave, so what's a little spinal puncture between friends? Since Pinhead is not a bruiser like Leatherface, and doesn't have the ability to overpower him — the Cenobites' calm demeanor and everyday physiques are part of what makes them so threatening — Pinhead would have to go along with it. And, given his propensity to sexual domination and submission, being speared would instigate something entirely different from a fight. Indeed, meat hooks are a common tool in Pinhead's toy box. Having his skin torn open by one is likely just a common Saturday night thing in Hell.
So while the panicking Leatherface could easily rip Pinhead down from the meat hook, toss him to the ground, push his nails in deeper, and even try to sever a limb, Pinhead would find himself happily going along with it, laughing and wincing through each piece of exquisite torture. Yes, Pinhead could conceivably "fight back" as it were, summoning chains and knives with a mere thought, but the pain he would inflict on Leatherface would be cruel. Pinhead doesn't kill and torture merely for the sake of it (well, except in "Hellraiser III: Hell on Earth," but most Pinhead fans tend to ignore that film's sloppy canon), preferring to find victims who deliberately summon him. Killing Leatherface doesn't provide the ironic pain/pleasure death that the Lament Configuration was built to provide.
Pinhead, being tactful and polite, would not harm Leatherface, and could summon chains as a mere safety measure, because it's not entirely clear if Pinhead could survive having his head fully removed by an errant chainsaw. After a few hours of Leatherface attempting to kill Pinhead, the two of them would merely be exhausted. Or at least Leatherface would be. The physical stamina of a Cenobite has never been established in any "Hellraiser" movies.
Time to play
Leatherface would be able to provide Pinhead an endless supply of pleasurable pain, and Pinhead can show Leatherface new techniques on how to craft the most fashionable leather goods possible. Bubba is a mighty craftsman, but his work is sloppy at best. Pinhead could help perfect his artistry. Ultimately, Leatherface and Pinhead would exist in a violent, albeit symbiotic, relationship, with the understanding that if Leatherface were to ever fail to hold up his end of the bargain, Pinhead would obliterate him and everyone he loves. After all, the saw is family.
Then, once Leatherface has honed his skills as a maker of leather fetish wear and the two had learned to effectively torture together ... well, part of the Hellraiser mythos is that worthy souls can be transformed into Cenobites. There's no reason why a man draped in tanned human leather and wielding hooks and cutting implements wouldn't ultimately be welcomed into Hell.