It's fun to think about who might win in a hypothetical fight between horror movie icons, but most of the time there is never any definitive way to settle those arguments. In the case of Halloween's Michael Myers vs Hellraiser's Pinhead, there was almost a movie that would have shown us the outcome of that exact scenario. Yes, according to Doug Bradley himself, a Halloween and Hellraiser crossover movie almost happened.
Doug Bradley is an absolute horror legend, having played Pinhead in the Hellraiser franchise ever since the first movie came out in 1987 up through 2005. The actor recently did an interview with Your Move Magazine and discussed in detail plans that existed for a Halloween and Hellraiser crossover movie that almost happened in the early 2000s. Here is what he had to say.
"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."
Freddy Vs. Jason came out in 2003 and made $114 million worldwide from a comparatively small $30 million production budget. So there is no reason to think a Hellraiser-Halloween movie wouldn't have been able to do similarly well. Especially with Clive Barker, who wrote and directed the original Hellraiser, writing the script and John Carpenter on board to direct. Even though no story details were ever released, the timing seemed perfect and the talent was there, so what happened? Here is how Doug Bradley tells it.
"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."
Michael Myers and Pinhead definitely occupy two very different spaces in the horror world, but so did Freddy and Jason. So there is no reason to think that they couldn't have made it work. Sure, a lot of Freddy Vs. Jason is pretty cheesy and over-the-top, but there is a lot of joy to be had for horror fans in watching those two legends duke it out. It would have been at least as entertaining to see the Halloween and Hellraiser crossover version of this. With the talent involved it could have definitely been something that was at the very least interesting, if not downright special.
This was more than a decade ago, so the odds of the movie ever coming to fruition at this point are much less likely, especially since both franchises have moved on. A new Halloween movie is currently in the works with John Carpenter producing, which is due out next year. The tenth Hellraiser movie, Hellraiser: Judgment, is currently being filmed. There have also been plans for a reboot of the Hellraiser franchise with Clive Barker directing and Doug Bradley set to star again as Pinhead, but there has been no word on that recently. So unfortunately, we are left with what could have been in terms of a Halloween and Hellraiser crossover movie.