1) meaning to be driving in a Import (i.e. Honda civic) and to have 20 inch wheels on it
2) to be riding a bmx bike that has 20 in rims or a 20 inch top tube
1) "Man, we be rollin on 20's up in this joint, ya hear?"
or
"Those 20's your rollin on are Bitchin!"
2) "man, i'm rollin on new 20's, check these bad boys out."
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