Top Definition
When walking past a young, middle class, caucasian male who is bouncing along the street, fully clad in wannabe-gangster Henley's gear, a Henley's Drive-By is putting your fingers in the shape of a gun and pretending to shoot them, so you can atleast pretend to free your streets of such a loser who'd obviously much rather be in the ghetto than living in a comfortable semi-detached house with his mum.
"Hey, look at that wigger over there! Who does he think he is in his Henley's hoody?"
"Yeh, definately think he needs a Henley's Drive-by".
by You ain't got no hope October 04, 2009

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