Circa: 1994
Producer: DJ Premier

Before his name carried weight in the hip-hop game, Jay found himself playing bit roles on some seriously heavyweight, if not exactly legendary, posse cuts. BK rap legend Big Daddy Kane took Jay under his wing in the early '90s, bringing him on tour as a sort of sideman/opening act (though Jay would actually rhyme in the middle of Kane's sets, during costume changes) and featured him on “Show and Prove,” a '94 track which brought some of Brooklyn's finest MCs together over a hard-hitting DJ Premier beat.

Okay, not all of the talent was fine. “Show and Prove” has the misfortune of beginning with Kane dancer Big Scoob’s Onyx-meets-the-Pharcyde flow, an absurdly affected style that makes Jay's double-time raps sound futuristic by comparison. Jay for his part found himself unfortunately sandwiched between an energized, “Shaft”-singing Kane and an all-the-way-turned-up ODB. Though he doesn’t exactly outshine him on the track, watch the video for "Show and Prove" closely: Jay seems to be on the receiving end of some seriously side-eyed glances from his former mentor BDK.