Big Daddy Kane may not be a household name to those who don’t bother familiarizing themselves with Hip Hop’s past, but a direct line can be drawn between Kane and emcees from a later era such as Jay-Z, 2Pac and Notorious B.I.G. The connection began in 1990, when Kane featured Queen Latifah, MC Lyte, Digital Underground, 3rd Bass and Jay-Z on his “Chocolate City” nationwide tour. For some, the tour provided both valuable exposure and a chance to get some tutelage.

“I would do half the show, and then I’d let Jay-Z rhyme while I went in the back and changed outfits,” Kane explained during TVOne’s “Unsung” profile. “Then I’d go back and finish the show.”

That would most likely be an understatement, as Kane’s younger brother, Little Daddy Shane added that Kane also helped Jay with his flow and securing studio time.

“I think he was considering starting his own label and might’ve had me in mind for a slot,” Jay-Z wrote in his memoir/lyric book Decoded. “I’m not sure, and nothing like that ever materialized. But I got an invaluable education watching him perform…even today I use some of the ideas I picked up back then about pacing and performance in my own live show.”

During the “Chocolate City” era, 2Pac was a roadie for Digital Underground, while Naughty By Nature held down the same duties for Queen Latifah’s camp. Mister Cee, who was Kane’s DJ at the time would ultimately end up mentoring fellow Brooklyn emcee Notorious B.I.G. during his early years as well as getting a few production credits on songs on which Biggie appeared.

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