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 Get the Ska Coolio mug.