My uncle was on
As we find out in the next line, the Cadillac that ScHoolboy was in was stolen from his uncle. “my uncle was on” points out how much his uncle loved the Cadillac and how it expressed who he was — he was literally the Cadillac.
This line also ties in Macklemore’s first verse when he says, “I’m rolling in that same whip that my granddad had”. These old school Cadillacs, at one point in the past, were stylish and hip, and the Cadillacs were handed down to the proceeding generations.
The type of car that a person drives is an expression of that person.
Even back in the day, cars got you women:
Now, imagine how mad his uncle was when ScHoolboy was “14…
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