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 boy

Coolio boy is you but cool!

Person 1:hey I am such a Coolio boy

Person2:hey me too!!
person1shut the fuck up

by therealcoolioboy June 15, 2024

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

Coolios

Explaining something exetremely cool

I love unicorns they are so coolios

by ZiplineZebras January 12, 2018

Coolio

An expression you use when you're a bogan or if you're stuck in 2006.

hehe

Man 1: Have a good day
Man 2 (stuck in 2006): COOLIO

by coolio12345678910 October 10, 2019

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

coolio

coolio- a better word than cool meaning that something is awesome.

Coolio, thanks for the help.

by idunnooo94 January 13, 2021