Ska Coolio Share definition Flag A word made by the coolest guy alive Tyler(rocky Point). Can Mean Cool Beyond Belief Or Just To Shut People Up. "Yeah Man I Have This Back Problem" "Ska Cooilio" ex.2 Yooo Man That Skate board is soo ska Coolio Ska Coolio by Randommness From Rocky Point October 14, 2008 0 0 Get merch Get the Ska Coolio mug. Buy Now — $32.95 See more merch