Green’s Dictionary of Slang

(US) intellectual, cultured.

1967		A. Baraka Tales (1969) 13: Will you listen to this little pointy head bastard calling me funny looking.
1972		Life 31 Mar. 41: There came the nemesis of federal judges and pointy-head intellectuals and briefcase-toting bureaucrats.
1974		Harper’s Mag. June 52: The pointy-headed bureaucrats, the Establishment, the system, the straights.
1984		Atlanta Constitution (GA) 30 Aug. 17/4: I helped the Gov’nuh blame it all on those ‘integrating, scallywagging, race-mixing, pointy-headed liberals who can’t even park their bicycles straight’ .
1990		(con. c.1970) G. Hasford Phantom Blooper 212: John Wayne movies murdered my son. Them pointy-headed politicians hung him up like a hog for slaughter.
2005		B. Gillette Dittoshead’s Guide to Adult Beverages 113: [...] depending on which pointy-headed elitist professor you consult.
2014		Gazette (Montreal) 15 Nov. 11/1: [cartoon caption] The toddler ate candy and sniffed wet paint until he became a pointy-headed boss.