Back when rappers wouldn't dare play lyrical roulette
With a automatic weapon I was rappin' with
The lyric is actually referring to the days when hip hop artists and songs were more of a party vibe (i.e. Sugar Hill Gang’s records) and/or conscious type rap (i.e. Grandmaster Flash’s “The Message”). Back then, rappers wouldn’t dare talk about guns and gangs and some of the violent things they’d done or seen in their hood on record because there was no way that would have sold. Back then Jay is saying that he was REPPING (not rapping) with a Tec 9. This is in reference to when he was a crack dealer.
It’s also a metaphor — word play of russian roulette and taking chances. Where they usually play with a revolver and it’s usually a 1 out of 6 chance of suicide, but to play with a tech is damn near suicide. So he’s saying while others were scared to take little chances, he was continuously taking huge risks in order to succeed..
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