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Zero cool
Zero Cool - adj [1950s-60s] 1. Very "cool"; as "cool" as possible 2. Very aware, current, and sophisticated (jazz, cool, beat, and student use)
Sources:
Wentworth and Flexner. The Pocket Dictionary of Slang. Pocket Books. New York.1976
Green, Jonathon. Casell’s Dictionary of Slang - 2nd Edition. Weidenfeld & Nicholson. 2005
Note:
"cool" as a slang term etymology:
Meaning "calmly audacious" is from 1825. Slang use for "fashionable" is 1933, originally Black English, said to have been popularized in jazz circles by tenor saxophonist Lester Young
source: http://www.etymonline.com