Jay was NOT "That Dude" when Reasonable Doubt dropped.
Folks were like "Is that Mary J Blige" when Cant Knock the Hustle came out.
He had a song with Biggie, which was a big deal cause of Biggie.
First verse of Cashmere Thoughts got Hip Hop Quotable in The Source, and they cut the last bar off it.

"From my nikka Sauce, I hit you with this advice:"
Too much music was dropping all over. Its gonna make some folks mad to hear it, but Real Live was getting more plays on Rap City than Jigga was . And I'm not hating, that's just the way it was.
He didn't get to be a big deal until Pac called him out. Then he became "Biggie's Best Friend, Jay Z" after Biggie died.
Wasn't nobody feeling "The City is Mine".
"Sunshine" got WAAAY more love.
"Streets is Watching" made him hot.
"Money Ain't A Thang/Hard Knock Life" made him stupidly famous and "That Dude"
"Lookit all these OFF BRAND nikkaS..... runnin around acting like they holding figures as big as Jigga's! THATS THAT BULLshyt!" Made us all pay attention to the fact that he was loaded and the Bentley he was driving in the Hard Knock Life promo was prolly his.
And there you go.