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

Coolioness

Coolness, but cooler.

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

by snellie January 1, 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

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

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 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

by Retr0z April 2, 2020

Coolio

a weird way of saying cool

that new pair of sneakers is so coolio

by waparoniandcheese'sbff February 26, 2020