Where does the British word "cheeky" originate?

There’s tons of british slang I would like explained, if anyone considers themselves an authority.

Great question @linuxgnuru

‘To give (someone) cheek’ is like the more American expression, ‘to give (someone) lip’. As in, ‘Don’t give me none of your lip,’ etc.

In these cases cheek, lip, and even jaw (like ‘he kept jawing on’ or something) metonymically represent the act of speaking. Thus someone who is ‘cheeky’ is someone who speaks too easily, with insolence or impudence, is glib, disrespectful, etc.

I’m not British so I don’t know whether the word’s meaning has expanded and can define non-verbal behavior as well. Maybe someone else can answer that. But the above is how the word originated.

Hope this helps.

Not an authority here…but, I believe “cheeky” has to do with the butt cheeks and acting like a bit of a “bum hole”.

Andy Capp weekly comics.

It has nothing to do with your nether regions. @absalom is correct. Here is a Kipling quote which makes this etymology clear:

“Shut up,” said Harrison. “You chaps always behave as if you were jawin’ us when we come to jaw you.”
“You’re a lot too cheeky,” said Craye.

EDIT: 1899, Rudyard Kipling, Stalky & Co

From dictionary.com (my fave):

1859, from cheek in its sense of “insolence.”

It’s the problem a chipmunk has when consuming too many nuts.

The word cheeky can also be used fondly… dependent upon voice tone to convey the intended meaning.

All I know is my grandmother used it frequently. “Yair a cheeky wee lad”. And she wasn’t really mad. She was just being affectionate.

Meaning of Cheeky depends on the context in which it is used. I often say to my g/daughter “your a cheeky little so and so”, and in that use is affectionate as has been noted above.
On the other hand I can talk about someone being officious and say “they’ve got a cheek”, meaning theyre overstepping themselves.

Speaking of Cheeky. This one (NSFW) is another in the master of soft core erotica Tinto Brass’s repetoire and his obsession with the perfect derriere.