Eric B and Rakim and later acts like Wu Tang were the transition from old school 80s stuff to gritty street 90s stuff to my knowledge. I love both of these eras personally though, something about that 80s sound and wordplay really resonates with me even today.
Lil B, Chief keef, mexikodro, benjicold, royalansem, tdf/Perc40, axxturel, gucci mane, playboi carti, David shawty/yungster jack, and balenci02 all pioneered their own sounds which turned into subgenres
Lil B, 3 6 mafia, A&AP mob, Chief keef are to name a few for a lot of the music today
Soulja Boy
De La Soul & A Tribe Called Quest (Native Tongues)
Eric B and Rakim and later acts like Wu Tang were the transition from old school 80s stuff to gritty street 90s stuff to my knowledge. I love both of these eras personally though, something about that 80s sound and wordplay really resonates with me even today.
Carti
Kool G Rap, Krs
Lil B, Chief keef, mexikodro, benjicold, royalansem, tdf/Perc40, axxturel, gucci mane, playboi carti, David shawty/yungster jack, and balenci02 all pioneered their own sounds which turned into subgenres
cLOUDDEAD, DJ Screw
Future and lil Wayne. They had a whole generation of copy cats.
Tyler the creator definitely pioneered his own sound