Green’s Dictionary of Slang

chuckleheaded adj.

[chucklehead n.]

foolish.

[US]A. Hamilton Tuesday Club Bk V in Micklus (1995) 89: Why should any saucy, pert, demure [...] coxcomb of a Clubical Critic, to say no worse of him, nay, any Chuckleheaded, unexperienced, raw, Saucy Jackanapes pretent to say, that this our famous History, is more triffling than any other history.
[UK]Bridges Homer Travestie (1797) II 31: You think the rock of Troy / Some chuckle-headed booby boy.
[UK]Bridges Burlesque Homer (3rd edn) 291: [as cit. 1762].
[UK]Grose Classical Dict. of the Vulgar Tongue.
[UK]Lex. Balatronicum.
[US]R. Waln Hermit in America on Visit to Phila. 2nd series 28: She was [...] Cribbage-facedBeetle-headedBottle-headedBuffle-headed,—and Chuckle-headed!!!
Limerick Reporter 6 Aug. 4/3: Troops of chuckleheaded little English aids, plump and platter-faced.
[US]Whip & Satirist of NY & Brooklyn (NY) 6 Aug. n.p.: That chuckle-headed Mr S who keeps a little grocery and grog-shop.
[US](con. 1843) Melville White-Jacket (1990) 247: When my brother arrives, he must consort more or less with our chuckle-headed reefers on board here.
[US]M.L. Byrn Adventures of Fudge Fumble 170: She was [...] a little chuckle-headed.
[UK]J. Greenwood Dick Temple III 190: The Billy to whom you are described as being ‘chuckleheaded’.
[US]H. Frederic Seth’s Brother’s Wife 124: I’m sick and tired of getting out telegraph for these chuckle-headed printers to throw on the floor!
[UK]J.K. Jerome Three Men in a Boat 56: One of those irritating, senseless, chuckle-headed, crack-jawed laughs of his.
[Aus]Truth (Sydney) 6 May. 5/6: Nobody but a chuckleheaded temperance fanatic would throw off such vapid twaddle.
[UK]H. Macfall Wooings of Jezebel Pettyfer 9: Who’s the most chuckle-headed idiot in the crowd?
[Aus]Sun. Times (Perth) 16 July 1/1: The chuckle-headed chump caught her absorbing ale with an Afghan.
[US]S.E. White Arizona Nights 9: I’d walked into it, chuckleheaded as a prairie dog!
[Aus]Sun. Times (Perth) 8 June 7s/4: It seems sad that a muddling, chuckle-headed set of legislators should be flies in the ointment.
[UK]W. Sickert Morning Post 6 June 5: Is it possible to imagine a more chuckle-headed error in reasoning in a paper with the title of Clarity?
[US]Z.N. Hurston Gilded Six-Bits (1995) 988: He so chuckle-headed, he got a pone behind his neck.
[US]W.R. Burnett High Sierra in Four Novels (1984) 285: Fat Evans, known to the grownups as ‘that chuckle-headed, lazy good-for-nothing.’.
[UK]C. Stead Cotters’ England (1980) 183: They’ve turned into chuckle-headed gossips.
[US]O. Hawkins Chili 65: This chuckle headed cracker-honky-idiot.
[US](con. 1975–6) E. Little Steel Toes 62: Trudging through the snow towards these chuckleheaded morons.

In derivatives

chuckleheadedness (n.)

foolishness.

[US]J. Jones From Here to Eternity (1998) 487: He knew it was only luck he thought of it, the catching at straws of a man paralyzed by his own chuckleheadedness.