Two problems, Pinhead has been straight to video since Bloodlines. So he's not a big name horror villain anymore. Plus, Bradley is too old and no one liked the recast. Second problem, Halloween and Michael Myers are no longer under the Dimension banner, they signed with Blumhouse. There would have to be some sort of deal to do a crossover. Freddy and Jason were both New Line, easy. Rights issues between 2 studios, who gets what, not easy.
"He came home." - Dr. Sam Loomis from the original HalloweeN
As cool as it would be to see those two awesome characters fighting each other, I would prefer that the mostly grounded Halloween universe didn't crossover with the more fantasy oriented Hellraiser universe.
I could definitely see Freddy and Pinhead existing in the same universe before Myers and Pinhead. And that would be kind of interesting if maybe Freddy ended up becoming a cenobite at one point.
Yeah he's awesome, and was a perfect choice for Hercules. My mom always had a huge crush on him and still does. That's why I saw the show all the time growing up.
In like 2003 an old buddy of mine actually wrote and was going to submit, a screenplay for this. Think Dimension was thinking of doing it for a short time back then, and he was trying to get in on that. http://lscottpalmer.blogspot.com/