When I was pushing weight, back in '88

from Jay Z – Takeover Lyrics on Rap Genius

Meaning

“Pushing weight” = selling drugs in large quantities

In Jay Z’s sometimes apocryphal autobiographical mythology, 1988 is a year in which he was dealing a lot of drugs and making a lot of money (cf. “I’m still spending money from ‘88” on “Dead Presidents II”)

Meanwhile, what do you think Prodigy was doing in 1988?

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