It is a concept from the UK not particularly shared by the US. It's basically sly and artful disrespect. Oscar Wilde, John Lennon, Jarvis Cocker , Noel Fielding, and Morrissey all come to mind with respect to being "cheeky". Having lived in England, I recognize this as a particularly British cultural phenomenon. There are always those in pop culture in the UK who aspire to be seen as quick-witted and cheeky. It's their way of "sticking it to the man" with a nudge and a wink. Being an American, I really don't see anything in the US that has quite the same tone. Sure there are plenty of smart humorists in the US, but they don't traffic in "cheek" quite like the Brits do. I think American humorists are more direct somehow. Cheek is done with a sly look in the eye because you know you're trying to get one over on the man, and the smile says that you know, and they (the man) know too, but you're allowed to get away with it anyway. It's very subtle. I'm guessing it has something to do with the more entrenched class system in the UK vs the US. Most Americans feel as if they are on par with the best of them (at least in their own minds), and don't humble themselves very readily in the presence of people from higher classes. They don't feel the need to be subtle in their scorn of "their betters" as they say. I think there was (and maybe still is) more at stake when you trash-talked up the chain in the UK. Just a guess.
When the Beatles were performing for the royals and John Lennon said... “For our last number I’d like to ask your help. Would the people in the cheaper seats clap your hands? And the rest of you, if you’ll just rattle your jewelry.” A perfect example of being cheeky. Poking at power with humor.
by Phydeaux2000 October 3, 2017
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Something said or done disrespectfully, but endearingly.
Dick(head) removed photos and Friends from Facebook in an effort to one-up me. That was cheeky of him.
by post-menopausal January 27, 2016
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Cheeky is a word used by english people like myself. 1. it is a word used to describe someone who does something or says something sort of disrespectful and sometimes rude, but says it in a cunning way. 2. can also be used in a more serious way i.e if you found out that one of your friends has been talking behind your back, you might say that she is a "cheeky bitch"
1. student says: miss, i like your sweat patches, i think they look nice against that lovely brown dress you are wearing today...

Teacher says: "dont be so cheeky"
by english gal July 24, 2003
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"Who's the cheeky (est) in the X factor house?"

Immediate answer: "Harry Styles."
by Dedicated Directioner January 10, 2012
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A word used mostly by people in the UK. It's a word that gives normally casual things an inappropriate feeling
Human - wow that was a cheeky handshake
*other human runs away and never comes back*
by newtie_ismy_cutie November 7, 2015
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Another term for quick or sly.
"Do you fancy a cheeky drink down the pub while the missus is busy."
by Helm Cheese July 25, 2003
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Someone who has no shame in doing something shameful or low class.
That cheeky hoe just walks right up and starts sucking his dick under the fukin table at the restaurant and the bitch didn't even know the nigga.
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