Green’s Dictionary of Slang

1. a state of drunkenness.

1629		J. Howell Familiar Letters (1737) I 5 July 220: I am sorry to have found Jack T. in that pickle, and that he had so far transgressed the Fannian Law, which allows a chirping Cup to satiate, not to surfeit, to mirth, not to madness [...] Jack T. I fear will die in a Butt of Canary.
1707		Farquhar Beaux’ Strategem V i: Enter squire sullen, drunk. [...] sir charles: But I presume, sir, you won’t see your wife tonight; she’ll be gone to bed. You don’t use to lie with your wife in that pickle?
1809		B.H. Malkin (trans.) Adventures of Gil Blas (1822) I 155: We drank hard, and returned to our employers in a pretty pickle, that is to say so-so in the upper story.
1898		Regiment 18 June 183/2: [W]ho should I meet but Private —— drunk, and having his face battered and covered with mud. Seeing him in this pickle, I asked him what was the matter.

2. a difficult, troublesome person, often a child but by no means invariably; ‘an arch, waggish fellow’ (Grose, 1785); also an amusing individual.

1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue.
1809		B.H. Malkin (trans.) Adventures of Gil Blas (1822) I 119: If the little gentleman is a pickle, they will lay the blame on your bad management.
1811		Lex. Balatronicum.
1812		Spirit of Irish Wit 116: A scapegrace young pickle who had received a considerable legacy.
1820		W. Combe Doctor Syntax, Consolation (1868) 176/1: ’Twas but a piece of Cupid’s fun: / That urchin is a very pickle.
1854		F. Smedley Harry Coverdale’s Courtship 28: Harry, restraining a strong inclination to lay his horsewhip across the young pickle’s shoulders.
1859		Matsell Vocabulum 66: pickle A smart fellow.
1865		H. Kingsley Hillyars and Burtons (1870) 7: The rest were terrible pickles, the most unlucky children I ever saw.
1883		Harper’s Mag. lxxvi 140: Tummas was a pickle – a perfect ’andful [F&H].
1891		‘’Arry on a ’ouseboat’ Punch 15 Aug. 76: Riparian rights? That’s the patter of Ahab to Naboth, of course; / But ’tis pickles like you make it plausible, louts such as you give it force.
1900		Derry Jrnl 12 Nov. 6/1: ‘Airy-fairy Lillian’ had married Dick Mosty nearly nine years ago. In those days Beratrice had been something of a pickle.
1902		‘Hugh McHugh’ It’s Up to You 76: Just then a little old Dutch pickle floundered out where we were and began to bite the top off the surf.

3. (also dead pickles) in pl., nonsense, rubbish.

1852		‘The Cadger’s Ball’ in Farmer Musa Pedestris (1896) 148: Bunn’s blaze of triumph was all pickles / To this wegetable shandileer.
1885		Referee 5 July in Ware (1909) 195/2: The promoters say that benefit will accrue to our Indian fellow-subjects by bringing before the English people actual representations of the methods of manufactures, amusements, etc., of our vast Indian empire, and will thus serve imperial interests. That, of course, is all pickles.
1908		K. McGaffey Sorrows of a Show Girl Ch. xiv: What do you know about the circus? Ain’t it all to the pickles?

4. a woman of a sour, unpleasant disposition [play on SE pickle, i.e. something/someone ‘sharp’].

1932		cited in Partridge Sl. To-day and Yesterday (1970) 313: If [a girl] is unpopular, she is a pill, a pickle, a lemon.
1970		Women Speaking Apr. 5/1: If a man doesn’t like a girl’s looks or personality, she’s a [...] pickle, prune [OED].

5. (orig. US) the penis; thus pickle lugger, as a term of abuse, a masturbator [resemblance to a pickled gherkin].

[1842		Whip & Satirist of NY & Brooklyn (NY) 25 June n.p.: With the other [hand] she seized the pickle [i.e. a cucumber], and cried ‘Dis is de biggest one I ever have in my hand’].
1949		in Randolph & Legman Ozark Folksongs and Folklore (1992) II 677: I gave her a nickel to suck my pickle.
1962		J. Quirk No Red Ribbons (1968) 198: Perkins, you’re a pickle lugger, you Rebel bastard.
1970		E. Thompson Garden of Sand (1981) 30: Imo’s pickle was black!
1978		L. Kramer Faggots 322: It’s time to take my pickle and get out of this pickle.