An expression on how something is... well, not cool. Very similar to the following expression: gay, retarded, lame, etc.
"Dude, you got drunk and danced naked in the middle of the freeway while singing "Jingle Bells" in Spanish?!"

"Dude, I know. Totally not cool."
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Not cool situation: When you get an "F" on your math test because you studied the wrong chapter... three minutes prior to the test ^_^
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*Bitch slap* <---- Not cool.
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Boyfriend: "I have something to tell you..."
Girlfriend: "You love me? =)"
Boyfriend: "Uh, I'm gay."
Girlfriend: "What? NOT AGAIN! This is SO not cool"
by Psych! November 27, 2005
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When someone has done something which causes you anger and displeasure. You respond by throwing down any item which you are currently holding and yell: "NOT COOL!". Of great importance: the item which has been throw down is now considered community property and may be taken by anyone witnessing said event.
Cool Guy: (walking into a room of friends/coworkers eating burritos) Dude, where's my burrito?
Not Cool Guy: I think they forgot to make it. Or maybe I forgot to order it. (smirks)
Cool Guy: (throwing down container of guacamole -- which he intends those in the room to now eat) NOT COOL!
by not cool guy eating a burrito January 14, 2014
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That shit just is not cool, man. Why'd you desert your homies at a time of need?
by Anon255 February 13, 2013
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(no doubt no doubt no doubt)

1) accepting something, with pain.
2) accepting something even though you know it's wrong
3) cooling down a convo
4) just saying it for fun, really
"Cool. Cool cool cool cool cool cool cool."

"cool cool cool cool cool. no doubt no doubt no doubt no doubt."
by 54345543 August 9, 2018
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It is one of Jake Peralta’s best catchphrases.
gun store cashier - “so how do you like your ammo, by the box or by the bucket?”
jake peralta - cool cool cool cool cool cool out country is broken :)
by urmum690 July 30, 2021
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An irony-proof phrase uttered by Abed on Community, denoting that something is so cool, it's "Who's the Boss" cool.
Prof. Sheffield: I have a wonderful idea. Why don't you teach the next class on "Who's the Boss" so that you can share your open mind with everyone in class.
Abed: Cool. Cool-cool-cool.
by bob beeflips April 19, 2011
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An expression said by Jacksfilms (Jack Douglass), a Youtuber, used as a calm response in order to hide your feelings or avoidance towards a comment or opinion that might be emotional, hurtful, embarrassing, etc.
"Mom said dad was going to be back from the store"
"How long ago was that?"
"12 years but he'll be back"
"Cool cool"
by Connie A. April 28, 2015
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