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.

by izzycorcoran October 9, 2023

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Coolioness

Coolness, but cooler.

“Bro you have so much coolioness today”
“Thanks bro!!!”

by snellie January 1, 2023

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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

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Coolio

Person has made/done/looks like something that is very cool and a lot of people like them.

Sarah : Hey Lily, I made a YouTube channel and i have 10,000 subscribers olny in 2 weeks!
Lily Repsonds : Woah, Sarah. You are very coolio!

by DoorsButBadV2HaterOnRoblox July 19, 2023

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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

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