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1.
Uber-cool, the pinnacle of coolness, with a hint of street.

Or

A very long way of saying "yes".
"Will Ferrell sure is coolioolio, yo!"

or

"Wanna get some frozen yoghurt or maybe a whole meal of food?"
"Coolioolio yo!"
by Miss Austin May 18, 2006

Words related to coolioolio, yo

brilliant cool excellent wicked yes!