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?"
