Green’s Dictionary of Slang

1. a fool, a simpleton.

1710		[title] Misfortunes of Simple Simon.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue.
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.
1839		Leeds Times 10 Aug. 6/2: How many [English Peasants]have been carried off to man your fleets, and when they came on shore again were no longer the simple slouching Simons of the village, but jolly tars, with rolling gait, quid in mouth [etc].
1846		Bath Chron. 28 May 1/1: A Simple Simon rambled into the Shambles, where the stocks are placed [...] he conceived that the punishment of sitting in the stocks was not quite so dreadful as represented and he must now try the experiement.
1857		Fife Herald (Scot.) 5 Mar. 3/5: I like Simon Simple very well, although he’s not quite so simple as he seems.
1859		Matsell Vocabulum 80: simon A simpleton.
1864, 1867, 1870		Hotten Sl. Dict. 230: simon, or simple simon a credulous, gullible person. A character in a song, but now common.
1872		Era (London) 8 Sept. 10/4: Few of us can have studied human nature [...] without having discovered a Sir Simon Simple [...] he great charm about Sir Simon Simple is his child-like simplicity.
1880		G.R. Sims Three Brass Balls 68: He had won the sobriquet of Simple Simon from his habit of talking to himself.
1882		Dundee Courier 15 Sept. 7/4: Why, what a Simple Simon you must be!
1893		Yorks. Eve. Post 1 June 3/6: [heading] Simple Simon. Simon Green was the name of a comparatively young man [...] in custody.
1903		Sunderland Dly Echo 15 Jan. 2/7: ‘Simple Simon’ up to date [...] It was stated that the defendant was selling pies [...] he had no license.
1904		Sydney Sportsman (Surry Hills, NSW) 16 Mar. 1/1: Quite a number of Simple Simons are wondering what induced a patron of one of the cutest stables in this cute country to buy the hurdle horse Again.
1912		Bulletin (Sydney) 17 Oct. 5/2: The Simple Simon eyes the wreck / So full of rage and drink; / I see him shake his head and neck, / I see his dim eyes blink.
1919		Register (Adelaide) 16 Sept. 9/6: The laughing jackass [...] is not rthe Simple Simon he looks.
1923		N. Anderson Hobo 76: L. was the ‘simple Simon’ in his home town.
1928		Hull Dly Mail 4 Apr. 10/4: ‘Simple Simon’ says ‘he believes in sport [...] ‘imon’ might be simple but Archie isn’t.
1933		Gloucs. Echo 2 Mar. 2/3: And He Must Be Simple Simon!
1947		Western Dly Press 16 Jan. 3/5: A magistrate described a defendant as something of a Simple Simon.
[1959		‘Paul Merchant’ ‘Sex Gang’ in Pulling a Train’ (2012) [ebook] A simon-stupid expression split what was left of his face].
1981		P. Reading ‘The Euphemisms’ in Tom O’Bedlam’s Beauties 42: Simple Simons / Asses, Owls, Donkeys, Mules, / Nincompoops, Wiseacres, Boobies, / Noodles, Numskulls, Gawks, Tomfools.

2. (drugs) a non-addict.

1959

J.E. Schmidt Narcotics Lingo and Lore.