cup and gander Share definition Flag 1. A real piece of shit; totally worthless. 2. Slacker, loafer. My glass piece is entirely cup and gander, not even a homeless man would use it too smoke the dirtiest rock ever. cup and gander by punisher December 16, 2004 0 0 Get merch Get the cup and gander mug. Buy Now — $32.95 See more merch