Green’s Dictionary of Slang

1. impudent, esp. in the context of a younger person failing to respect their elder.

1850		Lloyd’s Wkly Newspaper 16 June 1/1: We shall not be deemed profabne in permitting the parsons to associate themselves in our mind with the ‘cheeky’ urchins of St Giles’s.
1859		H. Kingsley Recollections of G. Hamlyn 259: ‘You will find, sir,’ said Lee, ‘that these men, in this here hut, are a rougher lot than you think for. Very like they’ll be cheeky.’.
1861		(con. 1840s–50s) H. Mayhew London Labour and London Poor III 134/1: And, perhaps, that makes us cheeky. [Ibid.] 137/1: The girls are wonderfully cheeky at fairs.
1880		Bulletin (Sydney) 16 Oct. 9/4: Spurgeon is a ‘cheeky’ youngster.
1889		Pall Mall Gazette 8 Nov. 2/3: The cheeky boy, with the natural ingratitude of youth, often makes a long nose at his master [...] [F&H].
1900		Boy’s Own Paper 10 Nov. 82: It seems a pretty cheeky thing for a youngster like me to try his luck.
1912		Bulletin (Sydney) 19 Sept. 48/2: He’s too cheeky for my taste, any’ow!
1939		K. Tennant Foveaux 71: I’ve met some cheeky brats in me day.
1946		D. Stivens Courtship of Uncle Henry 97: A cheeky look came over his face and he chuckled to himself.
1957		G. Kersh Fowlers End (2001) 105: It’s my money you’ll get, you cheeky little runt!
1965		F.J. Hardy Yarns of Billy Borker 93: He’s a cheeky mug. A joke’s a joke, but this is going too far.
1987		B. Chatwin Songlines 52: The leading lawman of Tribe C had the unforgettable name of Cheekybugger Tabagee.
1994		(con. 1970s) G. Byrne Pictures in my Head 66: The laughing, linking girls. ‘Get the last of the cheeky Charlies.’.
2001		J. Baker Shooting in the Dark (2002) 124: Now they say it’s us, our personal hygiene. Cheeky buggers.

2. (Aus.) bad.

1951

E. Hill Territory 443: Cheeky: Dangerous, poisonous. (‘Cheeky blacks’, ‘cheeky snake’, ‘cheeky yam’.).