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When you're travelling with too much momentum to be stopped, and will create huge destruction upon reaching destination.
Film quote from 'The Other Guys', used in conversation to indicate inbound destruction
Emilio: Lewis, why'd you run that guy over?
Lewis: Sorry, I was rolling heavy
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Similar to "Rolling Hot". When you drive around town with large weapons for self defense.
Roy: Sorry it took so long to get here.
Bill: What took so long?
Roy: I wanted to bring the best gun since we have to be rolling heavy in your hood.
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To bring an entourage of many men with you when you go out.
Look at him his group is huge hes rolling dude heavy.
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