Shoulda Stayed Down, Chack! Share definition Flag A phrase used when someone does something stupid, or something goes wrong. Person 1 trips over.Person 2: "Shoulda Stayed Down, Chack!" Shoulda Stayed Down, Chack! by whiteShadow00 June 14, 2009 0 0 Get merch Get the Shoulda Stayed Down, Chack! mug. Buy Now — $32.95 See more merch