I think Roc Marciano should have came out around the time
Forever dropped, dude would have had an awesome start as a Wu-Tang affliate spitting that pimp, godbody gutter shyt over soul samples. Debuts in '97, releases his debut in '99 produced by
Bobby Digital in Stereo era RZA. Guest features include GFK, Rae, Prodigy, EPMD, Busta Rhymes. Holds it down for Long Island with Busta through the 00's.

Rick Ross should have came out in 1995. In that timespan we all know rappers like Nas, AZ, Jay, Rae, Ghostface, Kool G Rap, Biggie were all doing the mafioso thing. Ross would have never been identified as a former correctional officer so his reputation wouldn't take a hit. He would be one of the best mafioso rappers and he would be considered one of the rappers that put the South on in the 90's.

Joey BADA$$ should have came out in 1993. He could have reached some good success locally especially. The Big Dusty single he released for his debut album sounds like some shyt that could have been on the first Black Moon album. With his age and skillset
The Source would be all over his dikk, and he'd be a mainstay on The Stretch and Bobbito Show. Big K.R.I.T. had he came out of Atlanta in the mid-90's. I think he would fit right in with the heavy bass sound and he would have fit right in with Dungeon Family, he would have made a great OutKast affiliate.
I disagree with some of these like someone said Lupe and Wale should have came out in the early 90's in the alternative rap era. IMO they came out at the perfect time post-
College Dropout. I think Max B came out at the right time, prison is really what fukked him up. Mos Def also came out at the perfect time, he came out with conscious rap strong and that hipster millennium neosoul strong. Digable Planets also came out at the perfect time.