Calvester and Winston Hill act like they are from opposite sides of the track when they actually just grew up on opposite sides of the room. Years later, Winston is a successful and wealthy real estate developer with a perfect and privileged family, but his life gets interrupted when his street smart, older brother Calvester finally gets out of prison and moves into the mansion. It's not long before Calvester begins parading his old prison cronies through the house driving the Hill family crazy - butting heads with Winston's trophy wife Ashley; seventeen year-old princess Heather; and housekeeper Su Ho. Calvester even teaches Winston's sixteen year-old son, Winston Jr. to be a gangster rapper.