Can a child be taught cheekiness, the way we teach manners or thoughtfulness, for examples? I don't think so. It has to be a trait that is inherited first, then "sharpened" when the child observes cheekiness first hand through his experiences. Some children are simply not cheeky whereas others can be labelled as one within minutes of interacting with them. Both my boys are cheeky and it is obvious to me where they get that trait from.
It always makes me laugh how Nicholas would bite the spoon I used to feed him water at mealtimes and then attempt to blow bubbles with the water in his mouth instead of swallowing it. He knows it makes me laugh, so he does it with a cheeky grin most times.
Marcus does cheeky things every day. He is the only kid who waves like a monkey with a cheeky grin in his first class photo when all the other kids just sit straight with a proper smile. He gives cheeky replies such as "oh yes, long long bus!" to my "how are you today" questions and asks cheeky questions like "mama, you want to eat the long long bus?" knowing perfectly well that it is inedible. Later he will correct me, if I say "yes" that I can't as the bus is made of metal. And let out an exaggerated "HAHAHA", accompanied with his move-head-in-clockwise-direction gesture. 6 year old Rohini from his class even told me one day outside the school that Marcus is a very funny boy. He makes everyone laugh. And he has a funny laugh which I suspect is this particular one, and when he laughs like that, it makes even the teachers laugh. And Marcus enjoys that attention very much. He was smiling with a huge cheeky grin the whole time while Rohini was telling me.