In (Late) 1999 My Favourite Active Rapper And Wrestler Were .........

[Wacky D]

good thing the OP stressed the word LATE, cuz if it was earlier in '99, both of my answers wouldve been different.

 

[OmegaK2099]

yeah 99 for me was the year for dre and even though he was jobbing out in championship matches the rock was still that dude on the roster having the entire crowd in his hand

 

[OmegaK2099]