Originally Posted by Heliomance
The build I was trying to make work before giving up involved the Jester from Dragon Compendium. As for the weird race I was talking about? Ragamoffyn, or maybe a Captured One. I thought it would be great fluff to have someone be a master of masks not through choice, but because an animated mask had attached itself to his face and wouldn't let go.
Captured One Jester would have been amazing from a flavor perspective.
EDIT: I don't think anyone used it, but Apprentice: Entertainer gives Perform as a Class Skill, and Apprentice: Criminal gives Bluff.