Green’s Dictionary of Slang

1. discerning, shrewd.

c.1698		B.E. Dict. Canting Crew n.p.: Long-headed, Wise, of great reach and foresight.
1711		Spectator No. 52 n.p.: But being a long-headed gentlewoman, I am apt to imagine she has some further design than you have yet penetrated [F&H].
1825		T.E. Hook Sayings and Doings 2nd Ser. 44: James felt assured that she was a very prudent long-headed person.
1830		Lytton Paul Clifford I 58: Bill was a longheaded, prudent fellow, and of a remarkably cautious temperament.
1836		T. Haliburton Clockmaker I 288: She was a considerable of a long headed woman, was mother, she could see as far ahead as most folks.
1849		Taunton Courier 17 Jan. 8/2: It’s amazin’ how long-headed men like Zerubbabel can be such darned idiots.
1862		‘Artemus Ward’ Artemus Ward, His Book 226: I know he’s smart. He is cunnin, he is long-heded, he is deep — he is grate.
1875		M. Thompson Hoosier Mosaics 129: That feller’s long-headed, he is. To be sure, sartinly, his barn’s a dern sight better’n his house, but his head’s level, for, d’ye see, that’s the way to make money.
1880		Bulletin (Sydney) 18 Dec. 4/4: Here’s a cove as is long-headed — Ninny knows his way about.
1882		Eve. Bull. (Maysville, KY) 20 June 1/3: Long-headed men are always on the alert to get possession of real estate after every period of depression.
1888		‘’Arry on Competitive Examination’ in Punch 1 Dec. 253/2: He’s a long-headed, ’ard ’itting cove.
1893		Salt Lake Herald (UT) 26 Mar. 9/1: Mr Popper is a long-headed man [...] He comprehended the wealth of valley and lake.
1896		Regiment 9 May 91/2: You may laugh, you may laugh, / I’m a man on the Staff, / Long-headed and wonderfully knowing .
1900		Boy’s Own Paper 10 Nov. 82: Those varmints aren’t as long-headed as they sometimes get credit for being.
1902		Ranche & Range (N. Yakima, WA) 16 Jan. 6/1: Oh no, not for fun — [...] but for very farseeing long-headed reasons.
1903		A. Adams Log of a Cowboy 378: That ought to be easy figuring for a foxy, long-headed Yank like you.
1904		Sydney Sportsman (Surry Hills, NSW) 14 Sept. 8/7: I’m long-’eaded myself, and it needs a wise man / To keep things straight.
1912		Bulletin (Sydney) 19 Dec. 22/2: Some long-headed member thought out this plan last December, observing that the civic claw had not, as yet, reached out for prohibitive rent for a Christmas Day matinée.
1913		Day Book (Chicago) 29 Nov. 12/1: Wilson is generally supposed to be very long-headed and astute.
1924		G.H. Lawson Dict. of Aus. Words And Terms 🌐 LONG-HEADED — Calculating person.
1969		C. Brown Mr Jive-Ass Nigger : .

2. obstinate.

1941		‘More Tennessee Expressions’ in AS XVI:1 Feb. 447/2: long headed. Stubborn. ‘Ross has always been long headed.’.
1969		C. Brown Mr Jive-Ass Nigger 6: There is somethin' wrong with that kind of nigger [. . .] if everything he says is a blasphemous cuss-word, if every time he opens his mouth it's a cocksucker, motherfucker-down-the-ditch-up-the-ditch-longheaded-sonofabitch.