Green’s Dictionary of Slang

cheek v.1

[cheek n.2 (1)]

to address in an impudent or insolent manner.

[[UK]‘Bashe Libel’ in May & Bryson Verse Libel 82: To speake like a Prelate, / To thinke like a Pilate / [...] / To cheack with his better].
[UK]Lloyd’s Wkly Newspaper 16 June 1/1: ‘You’re not cheeking it, I don’t think,’ said a young urchin to a ragged pal.
[UK]Dickens ‘Our Vestry’ Reprinted Pieces (1899) 247: Dogginson [...] informed another gentleman [...] that if he ‘cheek’d him’ he would resort to the extreme measure of knocking his blessed head off.
[UK]H. Kingsley Hillyars and Burtons (1870) 186: And with that end (as we used to say in those times) I ‘cheeked’ the detective.
[US]L.H. Bagg Four Years at Yale 43: Cheek, brazen audacity. Used also as a verb.
[UK]J. Greenwood Tag, Rag & Co. 9: But you shouldn’t have cheeked ’em Tommy.
[Aus]Bulletin (Sydney) 5 July 12/3: He told the kiddies to run away / And help mama, not cheek her .
[UK]R. Whiteing No. 5 John Street 259: If they cheek ’er, she’s sure to give it back agin.
W. Sickert Art News 10 Mar. 144: One of these days, I shall cheek her, I know I shall!
[UK]E. Raymond Tell England (1965) 128: You’re a ripping chap, and I’m sorry if I ever cheeked you.
Esex Newsman 12 july 3/2: He said he threw it at a friend who ‘cheeked’ him.
[Aus]D. Stivens Courtship of Uncle Henry 51: What was Freddy Welsh cheeking you about?
[UK]Willans & Searle Complete Molesworth (1985) 12: He [...] cheeks everybode.
[UK]P. Willmott Adolescent Boys of East London (1969) 40: You do things you wouldn’t do on your own – smash things up, just for a laugh, or cheek some old man.
[UK]Wodehouse Much Obliged, Jeeves 74: Different from a barmaid. She cheeks the chaps.
[WI]L. Goodison Baby Mother and King of Swords 68: There were a lot of [...] pretty uptown girls who were cheeking him after he did stage shows, women who loved to hear the slackness.

In phrases

cheek it (out) (v.)

to face down, to brazen out.

[UK](con. 1840s–50s) H. Mayhew London Labour and London Poor I 406/1: Persons as was coming the same road persuaded me to go and beg with them, but I couldn’t cheek it.
[UK]C. Hindley Life and Adventures of a Cheap Jack 311: Instead of admitting his error, [he] ‘cheeked’ it out by saying, ‘But you was there, wasn’t you?’.
[UK]Nottingham Eve. Post 28 Jan. 4/5: I told him if he’d send them in to the swell cribs he’d get a quid [...] but he said he couldn’t ‘cheek’ it.
[US]E.H. Babbitt ‘College Words & Phrases’ in DN II:i 26: cheek, v. i. In phrase ‘cheek it,’ to go into recitation unprepared as if prepared.
cheek it through (v.)

(US campus) to assume an air of (spurious) confidence.

[US]W.C. Gore Student Sl. in Cohen (1997) 16: cheek [...] 2. v. Cheek it through. To assume an air of confidence.