The 80s and the 90s was like night and day.
But honestly, the rappers (some of them) from the 80s were able to find new ground and stay afloat then...chubb rock, slick rick, rakim, etc come to mind.
Much more than rock...all them hair bands like Ratt, Motley Crue, Poison, were rendered irrelovent by the grunge movement come 1992.
By 1994 (which I consider the most defining year of the 90s) it was just a different world. TBH the mid to late 90s was probably the last exciting time in music for me. So many artists were coming out, MTV still played music videos, music stores were still poppin on many levels...the magazine game was interesting cause there was variety before everything started becoming corporatized and condensed and stripped down. By Spring of 1999 it was all coming to an end, which was in the fall of 1999.
2000s was nice cause you had 80s, 90s, legends sharing the same space as the new up and comers, but by 08...whatever.
I think other than Kanye and some others, this current era has no real legends.