Not since I was a young boy.

not fully, I've donned a wig or two but am going to fully commit to it pretty soon here

gotta work on my makeup skills

hell no, it's tacky and often lacks originality.

I've thought about it but honestly i just can't be bothered

Yes. I used to do Mariah Carey impersonations under my drag persona Carrie Messiah. I eventually branched out to do other music, though I kept the name!