6. Pinhead Vs Pennywise (Hellraiser/It)
A lot of horror fans were pulling for Pinhead Vs Michael Myers after Freddy Vs Jason, but I just don't see it. Pinhead's versatility and range of powers is too much for Myers, much like Freddy's should have been too much for Jason, had it been written correctly. Hell's Lord of Pain against a reality-warping creature in the form of a psychopathic clown... That's more like it. I imagine Pennywise terrorising a group of kids who have possession of Lemarchand's box and decide to unleash Pinhead and the Cenobites to cause a distraction to Pennywise, ultimately resulting in an epic battle which both antagonist parties would probably immensely enjoy.