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1) n. someone who simply looks downright cheeky (see cheeky).

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 ‘b-st-rd’ alone.
example for definition 1:
jackie chan.
although he is not necessarily manipulative and clever (most of his movies focus on his embarr-ssment and lack of understanding american culture) he can still be considered a cheeky b-st-rd 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.

stewie: hahahahaha!

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.

stewie: hahahahaha!

brian: you cheeky b-st-rd!
when you insert your p-n-s in between the left cheek of one girl and the right cheek of another girl and thrust at a rapid pace
dude i had a sick threesome with ruth and elane… they let me give them a cheeky b-st-rd
derived from the italian phrase “che quei b-st-rdi”, which literally means “the b-st-rds”.
this is simply an english adaptation of a foreign phrase made funny by the actual sound of the phrase. “che quei” sounds like cheeky, and b-st-rdi, well, you get the idea. che quei b-st-rdi, or cheeky b-st-rd. when you add the meaning of cheeky to the word b-st-rd, it offers a different meaning than simply the italian phrase che quei b-st-rdi. an amusing or endearing b-st-rd.
midget that sneeks past you and steals the golden gun
that oddjob is a cheeky b-st-rd
the act of putting ur p-n-s in between a big b-tt and simply grinding in it with out actual internal s-x.

-or-

the act of putting ur p-n-s inbetween the cheeks of a big b-tt
dude #1: wud u hit it?

dude #2: yeah, how bout u?

dude #1: yeah….

dude #1: d-mn look at that big b-tt joint im bousta cheeky b-st-rd that humongo …

dude #2: word up..