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.