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1.
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 'bastard' alone.
Example for definition 1:
Jackie Chan.
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.

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 bastard!
by TheShark06 September 25, 2006
 
2.
When you insert your penis 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 bastard
by Ryan Browson January 24, 2014
 
3.
Derived from the Italian phrase "Che quei bastardi", which literally means "The Bastards".
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 bastardi, well, you get the idea. Che quei bastardi, or Cheeky Bastard. When you add the meaning of Cheeky to the word Bastard, it offers a different meaning than simply the Italian phrase Che quei bastardi. An amusing or endearing bastard.
by BManJamz January 04, 2014
 
4.
midget that sneeks past you and steals the golden gun
that oddjob is a cheeky bastard
by oddjobteabagger February 05, 2010
 
5.
The act of putting ur penis in between a big butt and simply grinding in it with out actual internal sex.

-or-

The act of putting ur penis inbetween the cheeks of a big butt
Dude #1: wud u hit it?

Dude #2: yeah, how bout u?

Dude #1: yeah....

Dude #1: DAMN look at that big butt joint im bousta cheeky bastard that humongo ...

Dude #2: word up..
by mini-vanna white November 11, 2006