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Too Cool for School 

A phrase originating in the 1960's Counterculture.

It describes a person who has "tuned in, turned on and dropped out." In other words, it describes a person who has submerged themselves so much in the Counterculture (fully embracing a wide range of drugs- particularly psychedelic drugs, communal lifestyles, anti-materialism, radical politics, anti-authority and particularly anti-Police attitudes, alternate codes of dress and personal hygiene and often anti-social behaviors), and is thus "so cool," that they are largely unfit for and unable to participate in conventional society.

The phrase was invariably complimentary.

More recent usages tend towards extreme forms of irony. Often applied with considerable sarcasm as a form of insult it generally means a person who is deemed to have an inflated self-image. If the person displays any actual Countercultural leanings, they tend to be of the most mild possible variety.
"Dude, the Hells Angels are totally righteous. They're so out there, man, they're, like, too cool for school."

"That kid didn't come to my party. What does he think he is, too cool for school?"
Too Cool for School by The Egoist December 30, 2009
Related Words

Nice cool glass of shut the fuck up 

Boy 1: Your sister is hot, man.
Boy 2: Hey, do you want to come round and meet her, maybe I'll offer you a nice cool glass of shut the fuck up

california cool 

having that laid back, chill swagger that all the honeys love. basically not giving a fuck and kicking it with the homies and a lot of pot.
Creeper: "damn man Jared never gets pissed"
Hasselhoff: "he's california cool man."

That's a gold hat, cool cat 

Australian slang

Gold hat: a great idea

Cool cat: a cool, chill person
Person 1: I think we should order pizza tonight. What do you say man?

Person 2: That's a gold hat, cool cat!

are you cool?

1. Often said by pot smokers or dealers wondering whether you smoke weed or not.

2. Said by dealers asking if your a snitch/cop or not.
John: are you cool?

Sam: yeah dude pass me that joint!
are you cool? by cocainecowboy July 19, 2009

nigga be cool 

1. A large blunt instrument one uses to quell the aggressions of violent niggas.
2. The words uttered by the person immediately after brandishing said blunt instrument.
3. The words uttered by a nigga immediately after such an instrument is produced.
The cop snapped out his retractable baton and faced the perp.
"Nigga be cool"

"Ay Vern, I think I left my lead pipe in yo' car."
"Oh you mean the nigga-be-cool stick? Yeah I got it."
nigga be cool by MossbergPump September 17, 2008