Two-Shoe Cadillac Share definition Flag When you either don't have a car or your car is broke down, you're driving the Two Shoe Cadillac. I'm out of gas and I can't get any of my homies on the cell, so I guess I'm driving the Two-Shoe Cadillac. Two-Shoe Cadillac by crazybob541 January 6, 2014 0 0 Get merch Get the Two-Shoe Cadillac mug. Buy Now — $32.95 See more merch