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

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

Coolios

It’s like the coolio rapper but it’s coolios like the Cheerios

This post is so coolios

by Chase holstin November 4, 2022

Steve Coolio

The greatest R&B singer since Chris Brown in 2005. Often proclaimed by some to be better than Chris Brown.

Hey man, have you heard the new Steve Coolio song? That shit hits harder than Chris Brown

by JayDaWalker2005 September 27, 2022

Coolio

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

Pablo enjoyed The Coolio session

by Mylo Johnson January 14, 2022

Mr. Coolio

Boys who peaked in high school and thought they owned the school.

Oh, him? He peaked in high school. He was a Mr. Coolio.

by mrs hater January 16, 2022