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6 results for COOLCAT from Modern Era puzzles:

Repeated clues show (number of Modern Era occurrences).

Date	Grid	Clue	Author	Editor
Sun Sep 24, 2023	13A	Chill dude	Joel Fagliano and Christina Iverson	Shortz
Thu May 2, 2013	55A	Hipster (2)	Josh Knapp	Shortz
Mon Feb 1, 2010	22D	Beat Generation persona	Scott Atkinson	Shortz
Tue Jul 31, 2007	40A	*Hipster (2)	Allan E. Parrish	Shortz
Tue Nov 4, 2003	29A	Hip person	Elizabeth C. Gorski	Shortz
Fri Jun 7, 2002	38D	Daddy-o	Manny Nosowsky	Shortz

2 results for COOLCAT from Variety puzzles:

Date	Type	Grid	Clue	Author	Editor
Oct 4, 2009	Diagramless	12D	Hipster	Patrick Blindauer	Shortz
Oct 19, 2003	Acrostic	Y	Hipster (2 wds.)	Emily Cox & Henry Rathvon	Shortz

2 results for COOLCAT from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Fri Jul 18, 1986	39A	Hipster's cousin	Jones	Maleska
Sun Aug 11, 1974	98D	Hep one	Stafford P. Osborn	Weng

Anagrams:

37 ms