Ok, after spending some time thinking about it and reading some more ideas, I've managed to come up with a few...
Rayne: Alannis, or possibly Winnona Ryder (from around the time of Heathers)
Chasity: I was thinking someone fun and bubbly like Drew Barrymore circa Mad Love.
Willow02: Alicia Silverstone.
OLD MASTER: I was having so much trouble with this one. I really like the idea of Al Pacino, also, for some reason I was thinking of someone like Robin Williams for when you're in one of your more lighthearted moods... Am I completely off?
Mr. Pointy: I think that Chasity is on the right path with Jim Belushi...
LD: I don't know why, but I'm leaning towards John Cusak.
Chasity-- What comment about thin eyebrows? I can't for the life of me remember. Also, thanks for that, I really liked Milla Jovovich in The Fifth Element.