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
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Getting a rim job by someone from the Dominican Republic...
Pablo enjoyed The Coolio session
by Mylo Johnson January 14, 2022
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The same as “cool” but when you say “coolioit’s better.
Oh wow that’s coolio.
Coolio.
That’s pretty coolio my guy.
by Cocoloco12523456 December 23, 2020
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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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This word is a new cute way to say cool. It is mostly used by females. This word is also usually used in text messages.
Micha: Um.. do you wanna go on a date with me?
Erica: Yeah! That would be nice!
Micha: oh! I'll pick you up, tomorrow at The Git at 5:05?
Erica: Coolio! I guess it's a plan!
by Yuh Yuh YUH YUHH March 10, 2019
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