To go out and make a mess, spend a lot, get smashed, twisted, stoned, fight, party till morning, etc.
"Yo make sure you reach the club tonight, we're gonna roll hard tonight mofo!
An action, usually that takes place in a car (preferibly a Range Rover) and decribes the manor in which one is driving, usually overaggresive and at a high rate of speed.
Rolling Hard in the Double R.
He does not roll hard.
(it is also not uncommon for "nigga be driving" to follow this phrase.)