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Uncle Coolio's

The name of the restaurant in Orland Park IL that is part of the Uncle Julio's Mexican Restaurant chain. Known by Coolio's because 85 percent of the clientele looks like the rapper Coolio.
Hey Pat you want to head up to Uncle Coolio's today? No Tom, I don't feel like getting shot again. Let's go to Mama Maria's instead
Uncle Coolio's by Tom9750 November 11, 2013
A different form of the word cool, which can be used in almlst any situation, at almost every time.
Hey buddy, just came to tell you that my grandma died.
Coolio.
Coolio by Swagmaster828 February 20, 2022
Meaning cool, but typically used as a one word response and not part of a sentence.
Quaay says, "Hey, Inde, I just bought more ram for my computer!"
Inde replies, "Coolio!"
Coolio by Quaay July 4, 2004

cooliosos 

cool guy: Is cooliosos your new contribution to the language, like super mega awesome? It might catch on..
cooliosos by docmcsnoodles November 20, 2010

Coolioscoliosaurousotanious 

Usually meaning cool in a very excited matter.
Wow! your mom was so coolioscoliosaurousotanious in bed last night!

Coolio Iglesias 

Hybrid of Cool + Julio Iglesias.

You say "Coolio Iglesias" when you're feeling cheeky.

Salutes the delightfully cheeseball singer Julio Iglesias, who happens to be Enrique Iglesias' father.

It's like saying 'that's so cool/sexy/fly/bangin, it's got Julio Iglesias status'.
Example 1:

"Ima be at your place at 8 - bottle of Jim Beam in tow."

"Coolio Iglesias"

Example 2:

Your girlfriend/boyfriend comes out of fitting room in aqua lamé tankini...

You: "Coolio Iglesias"
Coolio Iglesias by keralea February 2, 2013