I'll only do 90's & 2000's and get back to 80's since I have to think more on that.
90's: 2Pac, Biggie & Mary J Blige
2000's: Trae, Ludacris & Eminem
All of those were no brainers for me except for when it came down to Mary or Mariah in the 90's. Could go either way but picked Mary.