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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 03, 2017
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Cheeky, a word used in Australia by New Zealanders when flirting with the opposite sex. It's used in a playful manner when one is teasing.
Curtis your so cheeky, come here so I can kiss you.
by Harley Qu April 11, 2016
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An originally harmless and inoffensive word, cheeky had now been claimed by morons for sticking in front of almost any mundane activity you can think if in a vague attempt to make it sound more interesting by trying to imply that they shouldn't be doing it, therefore thinking they somehow look "cooler" or more "badass" because of it.

Alternatively also used by the same morons for describing something done more quickly than normal
1. Guy from that volvic advert "just stepped outside for a cheeky volvic"
Everyone watching said advert "by that you mean you drank some water, congratulations"

2. "Hey Tom, want to grab a cheeky pint at lunchtime?"
"Nobody likes you Rob"
by Capt Buttpants March 23, 2015
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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 23, 2003
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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 May 09, 2016
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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 January 10, 2016
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