The last Jay-Z song Biggie Smalls ever heard: “He made me play it 30 times”
There are a lot of tales Jay-Z has narrated throughout his legendary career, yet none of them is as dramatic as the one that covers the final song that Biggie Smalls heard of him.
Hov recalled in a recent interview sitting with his friend and mentor with his cassettes and hitting play on Streets Is Watching. Biggie did not nod and smile agreeably. He told Jay to rewind. Then again. And again. “He forced me to play it 30 times”, Jay remembered before finally giving me the tape. “I was like, just keep it”.
The song itself is on In My Lifetime, Vol. 1, the 1997 sequel to Reasonable Doubt by Jay. It is one of the most raw songs on the album, a song meant to preserve the gritty nature of the hustler, as the album felt rather commercial elsewhere.
Jay has indicated that the song was the first track that he produced in the album, which is why it held so much weight during his process. That Biggie, the king of New York rap, was on it, and wanted it played over and over again was a halo no critic or position on the charts could bestow.
“The entire album will sound like that?” One of the numerous rewinds was requested, supposedly by Biggie. This was half-teasing, but half-serious, a sort of prophecy. In some way Jay was moving out of the strictly underground vibe of Reasonable Doubt and into a broader focus, but this track reminded Biggie that the streets remained centre-stage. At that, Biggie was not merely a colleague. He was blessing, moulding the confidence of Jay as he planned the next step to his career.
The memory is now bittersweet. Not much later Biggie was killed, and Streets Is Watching has borne the added burden of being the last Jay-Z song that he ever sat down to. It was a unique opportunity to Jay to present something new firsthand to his idol and give instant feedback, which leaves the kind of conversation that builds legacies.
To the hip-hop genre in general, it is like two giants conversing halfway, one standing on the verge of international stardom and the other making his final statements. That tape was not a repeat song. It was a repetition of history thirty times round.