Green’s Dictionary of Slang

a dolt, a simpleton, a fool; thus the fool’s head; also attrib.

1737, 1759, 1760, 1776		in Bailey Universal Etym. Eng. Dict.
1748		Smollett Roderick Random (1979) 10: Is not he much handsomer and better built than that great chucklehead?
1762		Bridges Homer Travestie (1764) II 140: Long since I pulled out Hector’s eyes, / But your great chucklehead denies.
1772		Bridges Burlesque Homer (3rd edn) 34: For which, by all the Greeks ’tis said / Your son has got a chuckle head.
1781		Hicky’s Bengal Gaz. 19-26 May n.p.: Nat Chucklehead [...] metamorphosed himself by having [...] his mischeivous mangy Head Shaved close and bare.
1797		Bridges Burlesque Homer (4th edn) I 47: [as cit. 1772].
1823		‘Jon Bee’ Dict. of the Turf, the Ring, the Chase, etc. 51: Chuckle-head — Heavy supper-eaters, nappers after dinner, turtle, fish, and venison mangers [...] become meaty about the nob, throw out carbuncles [...] and the tongue chuckles like an old hen in the poultry-yard.
1832		Satirist (London) 21 Oct. 341/4: ‘Tell me, chucklepate. when does Mary, thy Royal mistress, most resemble Cupid telling a story?’.
1844		‘Jonathan Slick’ High Life in N.Y. II 208: I was a darned old chucklehead to stump you to strike me.
1849		A. Harris Emigrant Family II 125: Ned – a young scion of England’s rural democracy, whose habitual title was ‘Chuckle-head’.
1851		R.S. Surtees Young Tom Hall (1926) 59: He belonged to poor Charley Chucklehead of the Bluth, who drank himself detheased.
1851		Life in Boston & N.Y. (Boston, MA) 28 June n.p.: And lo! the minister had a chucklehead, and was a snipe of goodly presence.
1859		Bathhurst Free Press (Aus.) 3 Aug. 4/1: Select Poetry War! War! War! [author] Chucklehead.
1863		E.K. Wightman letter 27 Jan. in Longacre From Antietam to Fort Fisher (1985) 106: Are the chuckle heads in Washington beside themselves: Will they never be done with their awkward bungling?
1864, 1867, 1870		Hotten Sl. Dict. n.p.: Chuckle-head much the same as ‘buffle head,’ ‘cabbage head,’ ‘chowder head,’ ‘cod’s head,’ ― all signifying that large abnormal form of skull always supposed to accompany stupidity and weakness of intellect; as the Scotch proverb, ‘muckle head and little wit’.
1889		J.K. Jerome Three Men in a Boat 116: No, you’re not, you chuckle-head, you’re singing the Admiral’s song from Pinafore.
1898		H. Macilwaine Dinkinbar 69: Any idiot can run this station better than I can myself, only I happen to want a particular brand of chuckle-head.
1900		Queenslander (Brisbane) 2 June 1022/3: Come out of that, you chucklehead.
1906		Dly Public Ledger (Maysville, KY) 18 Sept. 1/1: Big Chucklehead Threw a Big Rock into Concrete Mixer.
1910		W. Gippsland Gaz. (Warragul, Vic.) 8 Nov. 4/4: What scientific chucklehead was allowed to name a line of mountains Opthalmia Range?
1913		F.K. Sechrist ‘The Psych. of Unconventional Lang.’ Pedagogical Seminary Dec. n.p.: Slang [...] knows how [...] to work the poppycock racket on any daffy squirt or dotty chucklehead or dippy mushhead, or any crazy kioodle or concatenated chump [W&F].
1920		Marvel 19 June 4: Yes, old chucklechump!
1927		(con. 1835–40) P. Herring Bold Bendigo 193: Has the big chucklehead given up prize-fighting yet?
1934		W.R. Burnett Goodbye to the Past 58: ‘That’s what a brain’s for; to keep a man from working. It’s only chuckleheads that work’.
1943		D. Burley N.Y. Amsterdam Star-News 6 Feb. 13: Some chuckle-head street-corner cat.
1948		Z.N. Hurston Seraph on the Suwanee (1995) 848: If that chuckle-head of yours was a hog head, I’d be willing to work for it for a solid year.
1952		W.R. Burnett Little Men, Big World 198: It’s important, Zand. Don’t be a chucklehead.
1968		(con. late 19C) S. Longstreet Wilder Shore 69: Turner saw beyond the flapdoodle of frontier rapscallions acting like chuckleheads or merely working off high spirits in horseplay.
1981		P. Reading ‘The Euphemisms’ Tom O’Bedlam’s Beauties 42: Addle / Silly / Chuckle / Dunder / Sap / Bone / Block / Thick / Muddle / Crack- / Heads.
1995		A. Heckerling Clueless [film script] C’mon you chuckleheads, get in here!
2001		‘Randy Everhard’ Tattoo of a Naked Lady 6: Any chucklehead can win all night long.
2016		tabletmag.com 31 Dec. 🌐 some chucklehead wrote an essay asking if Jews “use” the Holocaust too much, in maybe the Guardian?
2020		D. Winslow ‘The San Diego Zoo’ in Broken 138: The other [fighter] is pure chucklehead.