Here's who Robert Englund thinks would win in a fight between A Nightmare On Elm Street's Freddy Krueger and Hellraiser's Pinhead. The 1980s was a rich decade for new horror icons, with the decade spawning Jason Voorhees, the Predator and Chucky. Freddy Krueger is one of the most beloved, with the slasher being a good deal more verbal than most of his contemporaries. The franchise's use of dreams and nightmares also allowed it a good deal more creativity in how he dispatched victims.
Horror author Clive Barker delivered an instant classic in 1987's Hellraiser, where a man escapes from Hell and enlists his lover - who is also his brother's wife - to feed him victims so he can regenerate. The film introduced the monastic demons dubbed the Cenobites, with Doug Bradley portraying Hellraiser's "Lead Cenobite." Bradley's demon soon became better known as Pinhead, and the sheer uniqueness of the character made him another horror favorite.
While horror fans often daydreamed of how bouts between certain famous slashers would play out, it wasn't until 2003's Freddy Vs Jason that such a crossover finally happened. One alternate ending planned for this monster mash saw the titular killers brought to Hell, where Bradley's Pinhead would make a brief cameo. While it was a cool idea, New Line didn't have the rights to use the demon, so it's unlikely Freddy or the Hell Priest will ever appear onscreen together. That said, Robert Englund believes Freddy would win in that brawl - or at least under one specific condition.
While talking with Dread Central in 2020, Englund was asked who might win in a hypothetical Freddy Vs Pinhead fight. The actor explained Freddy would probably win since everybody - even monsters like Jason or Pinhead - have to sleep. "If they encounter Freddy and they sleep, at some point in whatever their world is Freddy can get to them." This logic tracks, considering Freddy bested Jason in their first dreamworld fight, where the dream slasher used Jason's fear of drowning against him.
That said, Englund also states Freddy could use whatever frightens the dreamer against them, but it's hard to imagine much of anything being scary to Pinhead. Perhaps Freddy could use Pinhead's own dormant humanity against him, but it would be fairly creepy to see what Pinhead's dreamworld would look like. While Hellraiser will receive a new movie reboot and TV show, the Nightmare On Elm Street franchise is currently on hiatus since the 2010 remake. It's hard to imagine anyone but Robert Englund donning the razor finger glove or fedora, but a recasting seems likely for whenever Freddy reappears.