Coolioolio Share definition Flag See coolio. It's meaning is the same of coolio, but this one is usually only used when something is EXTRA cool. "Man, that lion just ate a LLAMA! Coolioolio yo!" Coolioolio by Caitlin March 28, 2005 0 0 Get merch Get the Coolioolio mug. Buy Now — $32.95 See more merch