He's not my personal pick for all-time greatest, but he's a completely valid choice, imo more than Pac (who as an icon is near untouchable but as a musician/rapper ranks below numerous MCs) and Biggie (who only had two albums, albeit two great albums).

Saying Jay's only considered to be a GOAT contender because people hear him say it and make that leap doesn't hold at all. If that were the case literally every rapper would be talked about as an icon, since braggadocious shit has always been a part of hip-hop and nearly everyone does it.

Small Club 8.19.88 is an incredible live recording of an aftershow from that era, amazing energy, ridiculous solos, and good sound quality to boot.