It has to be Boy George. I believe before him no other Gay guy was as flamboyant and expressive in their style and dress on stage. I also watched a documentary about GB and when he went to America they were like WTF?
I don't know much about Cyndi Lauper but from what I understand she got overshadowed quite early in her career by Madonna. Madonna basically ripped off Cyndi's styling and took it too a whole 'nother level.