Coolio

Super duper snazzy

Faith is looking very coolio today

Coolio

Possibly the cringiest way of saying cool

Your coat is coolio

Coolio

A way to say something is awesome or amazing that's more interesting than just saying "Cool"

James: "dude my dad just bought me a car"
Jason: "oh coolio"

coolio

a person who is cool

you are so coolio

Coolio

Youngin's lingo for "cool". --e.e.c

U got your kicks from melrose? Coolio!

Coolio

A black rapper that appeard in 1994 and has a billboard #1 song named: Gangsta's Paradise
a really underrated rapper

Matt: who sings Gangsta's Paradise?
John:Coolio

Coolio

A saying said by faggots that enjoy being pegged by their girlfriends.

“What do you wanna do tonight… wanna get pegged?”
“Cooliooooo” says Matthew.