Hellraiser (1987) – I hate to be cliché, but let’s face it, his first was his best. We knew nothing about him except that he was malevolent, fair, and from hell. He didn’t even have a name. The mystery of who and what he was would come soon, but for a moment in time. We saw the face of unknown fear.
Hellraiser III: Hell on Earth (1992) – I know many people don’t like this film. I’ve always sort of felt that it was the Nightmare on Elm Street 4 of the Hellraiser series. You know, "young hip kids and a cool soundtrack." That being said, I enjoyed the idea of Pinhead unchained, so to speak, and his situation gave the character a lot of room to stretch. Loved it.
Hellbound: Hellraiser II (1988) – The reason why Hellbound slipped to the number 3 slot is that I don’t like the redemption of a villain. It was great seeing more of him and learning his backstory, but to have him find his humanity was crushing to me. We were just falling in love with him and he became something else. Alas, there are no room for tears…it is a waste of good suffering.
Hellraiser: Bloodline (1996) – Although regulated to second fiddle behind new cenobite Angelique, I still feel that this is one of his strongest outings, instilling him with a stalker like quality that doesn’t betray the character. For all the complaints that go along with this film, it’s a solid showcase for Pinhead when he does appear.
Hellraiser: Hellseeker (2002) – The main reason to rank Hellseeker this high up is it’s a return to the original. Just the few moments that Kirsty and Pinhead share are enough to give a sense of completion to their journey and make the whole thing worthwhile.
Hellraiser: Inferno (2000) – Pinhead is more of a whisper in this film but the solid story (which is akin to the anthology comic series), makes it a decent entry. Directed by Scott Derrickson, Pinhead is in a human guise nearly the entire film, but makes a fine appearance at the end. The strength of the film gives it meaning but you can’t help but wish Pinhead had been given more to do in the last of the decent films.
Hellraiser: Deader (2005) – Wait where is Pinhead? This film was not a Hellraiser script at birth. True, many of the DTV entries were original horror scripts, but this one commits the criminal act of giving Pinhead a decent set piece, then reducing him to little more than a cameo. Of course, Doug Bradley makes the most of it, but still.
Hellraiser: Hellworld (2005) - Also released in 2005, Hellworld once again gives us the character of Pinhead sparingly and has fellow awesome actor Lance Henriksen step up. Pinhead really can’t be judged in the mockery, but needless to say, Doug Bradley doesn’t embarrass himself. His final appearance as Pinhead is a sad goodbye. Just a wave from a passing car in the dark.
Hellraiser: Revelations (2011) – I wish there was something good to say about this ridiculous film. It is soulless and devoid in purpose, save for the fact that it allowed Dimension to hold on to the rights. Doug did not come back for this one and his replacement comes off as some weird asshole in a Halloween costume. All that this amounts to is a slightly higher budget fan film that you could buy at Walmart.