Ransom So Far Gone Drake

black Ferrari with the red seats, I call it playin' checkers

Drake is simply saying that he nicknamed his Ferrari (or driving it) "playin' checkers" because it is black with red seats
edwar.caleb
black and red are the color of the squares on a checker board and he's playin' and rakin' in Gs (making money) so he bought himself a Ferrari using his earnings
pauloptimus