Empress Maude is Erica Kane.
I'm not as big a fan of the daytime soap All My Children as my wife, but Susan Lucci's character makes a pretty compelling Empress. She's smart, tough and motivated by a grasping desire to be the top dog, but also a sympathetic character because she's weathered so many of the men around her doing their damnedest to wreck up her life.
The only King Stephen that could go toe-to-toe with this Empress Maud is J.R. Ewing, of Dallas fame.
The only man as greedy and lovably vicious as Erica Kane. Instead of coveting Ewing Oil, our audacious J. R. sets his sights on a crown never intended for him. And even though he can be a total son of bitch you want to punch in the face, he still has his tender moments and certain sentimentalities. He might fight tooth and nail to get what he wants, but he also knows that in a family feud there are a few lines you shouldn't cross. Or at least if you cross them, don't get caught.
Also, don't mess with King Stephen when he has his magic bottle handy.
Henry of Blois is Bruno Gianelli.
Undoubtedly Bruno Gianelli is less well-known character than the two biggest stars in soap opera history. Played by the late Ron Silver, Gianelli was the manager for President Bartlett's re-election campaign in season 3 of The West Wing. (Which incidentally, is pretty much my favorite TV show that doesn't involve swords or robots.) But four years later Bruno jumps parties to do campaign consulting for Republican senator Arnold Vinick. Gianelli is smart, tough and a bit of a womanizer. He's got a clear sense of right and wrong, but to some extant he'd rather win dirty than lose fair.
Henry of Blois is Archbishop of Winchester (or Wintoncester, as it is known in my campaign, which uses Thomas Hardy's naming conventions) and Abbot of Glastonbury. His refusal to give up control of Glastonbury when advanced to bishop suggests to me that he knows something about that ancient site's Arthurian connection. Henry is also a younger brother of King Stephen and quite probably the richest man in England. He's a power-behind-the-throne figure like Gianelli. Henry is also a lavish patron of the arts, especially architecture.
Henry changes sides at one point during the anarchy, which is what inspired me to match him up with Silver's character. It looks to me like Henry of Blois switches allegiances simply because he wants to be on the winning team. Bruno Gianelli has a much more nuanced and interesting motivation. I like the idea of keeping my options open by thinking of Henry as Bruno. Maybe Henry is playing the game on a whole different level, engineering the situation for the overall betterment of the realm, whoever ends up on the throne. Whether that makes him a good guy in the eyes of the players will probably depend on which side they take in the conflict.