Conversation so far:
What was Pinhead (Hellraiser)'s personality like?
I find intelligence scary, particularly twisted intelligence; it's one of the reasons why Hannibal Lecter is scary, isn't it.
What else can you tell me about his personality?
Pinhead prefers using coercive methods in order to obtain his goals, a fact which brings him into conflict with his ally, the demon Princess Angelique.
Did he have more than one personality?
In his demonic incarnations, Pinhead is irreverent toward Christianity: in the third film.
Did his personality have any weaknesses?
CANNOTANSWER.
Are there any other interesting aspects about this article?
Paul T.
Taylor, who portrays Pinhead in Hellraiser: Judgment, described the character as "twisted and intelligent".
Did any one else say anything about his personality?
Pinhead can be reasoned and bargained with.
In both Hellraiser and Hellraiser: Hellseeker, Kirsty Cotton bargains with Pinhead to offer him more "souls" in exchange for her own .

Question: Was pinhead ever a nice person or was he always evil?
Self-contained rewrite: Was Pinhead ever a nice person or was he always evil?