2) n. Someone who is very manipulative, clever, and self-centered.
This word is usually used in a joking manner rather than with a serious tone.
Can be used as a playful insult against someone who has wronged you but did no real harm. In most places it is ironically considered less offensive than using the word 'bastard' alone.
Although he is not necessarily manipulative and clever (most of his movies focus on his embarrassment and lack of understanding American culture) he can still be considered a cheeky bastard due to his unique facial expressions and his ongoing awkward encounters with attractive women where Chris Tucker or Owen Wilson are usually very closeby.
Jackie Chan's cheekiness is a clear result of him trying to be a quick, sly undercover cop in action-based comedies based upon stopping crimes in foreign countries (usually committed by evil greedy people who are also by definition ... cheeky).
Example for definition 2:
This describes Stewie from Family Guy to a tee:
Brian: Oh my god, where's my roast pheasant?
Stewie: Hmm. By now, I think its in my lower intestine.
Brian: You ate it? But I told you my boss was coming here for dinner!
Stewie: Well, unless he likes pork rinds, he's going home hungry.
Brian: You cheeky bastard!