Complex.com has a really cool feature in which they compiled 17 tracks featuring a pre-"Reasonable Doubt" Jay-Z. It's impressive because, despite what most would assume, Jay had actually begun his recording career 10 years prior to his solo album dropping, and thus acumulated quite a wealth of material before anyone really knew who he was. His first appearance on wax was at the age of 16 (!) on High Potent's "HP Gets Busy." (below) And he sounds so cute and non-threatening, too. I wonder if this was before or during his stint as a drug kingpin? Let's hope it was before.
Besides the sheer novelty, there are some really choice cuts in this selection, like a DJ Premier production featuring Big Daddy Kane, Shyheim and Ol' Dirty Bastard, as well as J-Hova circa '94. Also peep the classic seven minute freestyle between Jay and Big L. Both rappers show up to play, although I have to say, Big L definitely runs things as he was wont to do. I can't believe stuff that good was on the radio at one point in history.
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High Potent "HP Gets Busy" (featuring a 16-year old Jay Z in 1986)