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1.
A more stylish way of saying maximo coolio
"Dude! This is coolio to the maximo!"
by Scott J Martin September 24, 2006
 
2.
An extremely cool moment
even cooler than uber cool, its almost like the uberness of uber cool
"I'm so uber cool"
"well beat this I'm coolio to the maximo
by Hoare May 22, 2008