Coolio

Getting a rim job by someone from the Dominican Republic...

Pablo enjoyed The Coolio session

by Mylo Johnson January 14, 2022

Coolio

Super duper snazzy

Faith is looking very coolio today

by Cooliolol December 20, 2020

Coolio Awesome

When something is extremely cool, and also very awesome.

Bro: How would you describe me?
Me: Mmm... coolio awesome.

by dsaadree December 17, 2023

Coolio

A truly epic singer who raps with such raw heat and passion that makes even Biggie Cheese whimper at the sight of him.
This dude is seriously unstoppable.

Guy 1: Wanna watch "Gangsta's paradise" by Coolio with me?
Guy 2: Naw, I feel ashamed whenever I hear him speak I get paralyzed by the insane power he contains inside him.
Guy 1: Man, that's true. I don't think I could survive such a godly force. I have been acquainted with all the wonders in this world and have now surpassed the need for material goods.
Guy 2: kapeesh, brother.

by Drallaby Drallabijo November 21, 2021

Coolio

A word used to let another person of the same sex that you are down for gay sex.

P1: Would you like to come over to my place for the night.

P2: Coolio

by Dudeone January 27, 2020

Coolio

a weird way of saying cool

that new pair of sneakers is so coolio

by waparoniandcheese'sbff February 26, 2020

coolio

cool but with a twist to make it more enjoyable to say cool

boy: mitchell is coming over to hang out
girl: coolio

by lil scar April 10, 2021