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cooler than a penguin on ice 

the ultimate cool; also, the ultimate compliment; a high degree of flattery
Katie is cooler than a penguin on ice.

cooler than the polar bear's toenail 

Trick Daddy's new album is cooler than the polar bear's toenail.

cooler than the other side of the pillow 

This phrase is an adjective used to describe someone who's demeanor is so cool that if you don't like them, there is something wrong with you; a literal description based on waking up at night, flipping your pillow, and the coolness making you feel so good you fall back to sleep.
Chris? Oh that dude is the shit! He's cooler than the other side of the pillow.

cooler than the other side of my pillow 

Something that is cool, neat, or nifty.

Ever notice how when you sleep with a pillow, that if your neck gets hot you can just flip your pillow over and the other side feels cooler than the side you were previously laying on?
Wow I really like that new tractor you got there, Bob! That thing is cooler than the other side of my pillow!

Cooler than ice 

Something really awesome beyond anything else
Mate your car is cooler than ice
That Joe cushion is cooler than ice
Cooler than ice by Liv_ingitup October 15, 2018

Cooler Than Denzel Washington With Mine

The Way You Do Your Thang Is Cooler Than Denzel Washington.A Song Chamillionaire And Z-ro Did Together.
Dont Try To Knock Tha Hustle Cuz Your Just Waisting Your Time.I'm Cooler Than Denzel Washington With Mine