When a poorboy pads his wallet with $1 bills and $5 bills, then puts larger bills on either end of the cash wad to impress friends or girls or strippers, fool them and make them think he's got lots of big bills. This is called a Poorboy Roll.
One stripper to another: Did you see how thick his wallet was?
Other stripper: No, it's a poorboy roll, once the 20's are gone, you'll see he just has 1's and 5's.
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