Pinhead vs. Michael Myers?! Who wins?!
I was told that the year before Freddy vs Jason was released, Dimension Films rejected two scripts for a Hellraiser-Halloween crossover, which was obviously where they would go because they owned both franchises. I was told the reason they turned it down is because they didn’t think it would work. They predicted that Freddy vs. Jason would bomb, but it opened at the top of the box office and stayed there for a second weekend – I think I’m right in saying that it was the first movie that year to do so.
After its success, Dimension wanted a Hellraiser-Halloween movie made immediately, so it was certainly going ahead. I had a couple of phone conversations with Clive [Barker] about it and I was getting quietly excited. Clive said he would write it and I heard reports John Carpenter would direct.
The version of events I got back on this is that the Akkad brothers, who produced Halloween, retained control of the sequels and didn’t want the crossover to be made. I guess they didn’t want Michael Myers hanging around with the likes of Pinhead.
As Bloody Disgusting notes, right around the time the Hellraiser and Halloween crossover was being considered, a poll surfaced asking fans if they cared to see Pinhead vs. Michael Myers, with the negative response thought to be a reason why the Hellraiser and Halloween crossover never got made. It's also noted no plot details are known.