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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.

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