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His first solo album yes, but I believe Mos goes back to the late native tongues era, bush babies, LONS, beatnuts etc. Blackstar I would consider 'underground'
While Mos first album was a classic, that was around the time people were moving away from the shiney suit era, that helped.
In the early 90's, Mos Def would have fit in. Because there was no stereotype of a rapper, it was about how good you were. Because every rapper besides the west coast had to be original, or you were deemed wack or a copy cat.
By the late 90's it had changed and the Puff and Master P era had taken over. Rap shifted and became more commercial and club.
A lot of dudes wouldn't have gotten deals in the early 90's, but they were helped out because they were the alternative by the late 90's. So they built careers off it.
A lot of **** is about timing and coming out at the right time. People like Nelly or DMX came out at the right time. DMX brought the streets and pain back. 50 brought the streets back. That's why the same dudes couldn't get deals or a release at one point, but a few years later could and came out and smashed ****.
Some **** I listened to back then, like J-Zone or Aesop Rock bores the **** out of me now. There's only a few artist from back then like that first Cannibal Ox, Non-Phixon and Jedi Mind Tricks that I can even **** with now.
You can be a underground rapper and become mainstream though. Eminem was a underground rapper. If Dre never hears him his career would have been totally different. He just had the rare talent of being able to craft songs that could appeal to the masses.