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Chillin' Like a Villain 

Relaxing comfortably, stress free in an attitude of ready to party.

The "Like a villain" part of the phrase refers to how rich gangsters may choose to be enjoying some liquor, maybe some fine wine, smoking a blunt of kine bud (high quality marijuana), enjoying 'chill pills' like blue valium or xanax and most likely listening to some music just enjoying the moment.

It's in the same urban family of "just chillin'" which is kind of like

how a wine would chill...not frozen, just simply appreciating in value as time passes.

A:"Hey man, what's up? What are you getting into? (like what are you doing right now or have planned later for the evening)

B: "Oh, you know the way I do it. Not much, just Chillin' Like a Villain here at the crib.

A:"That's what's up. Aright cool. Hey, why don't you come over to the house and we'll roll up a blunt, get high and drink on some of this crown I just bought?"

B:"Sounds like a plan to me. Give me about 30 minutes and I'll be out there."

A:"Cool, see you in a few. Peace."

B:"Peace."


chillin like a villian 

Seems that no one knows how this originated so let me break it down. It first appeared on the saturday morning cartoon Batman, where Batman approaches Freeze and Mr. Freeze says im chillin like a villan, hence why he was chillin (literal definition).
Batman: Freeze what are you doing?
Mr. Freeze: chillin like a villan
chillin like a villian by djnick November 3, 2003

chillin like a villain

Equivelant to "I'm fine, thanks." Can be found in many different forms(See examples)
Someone asks you: "Sup, dude?"
You say:
"Chillin'"
"Chillin' like a villain"
"Chillin', killin'"(Scary Movie)
OR for the extremely bored:
"Chillin', killin', and blood spillin' like a motha f**kin villain"
chillin like a villain by DJ Conan December 4, 2003

chillin like a villian 

Trent, 'spelt' is British English for 'spelled'.

Anyway, as said before, it's SPELT "chillin like a villAIN" not "chillin like a villian". It means you are really relaxed et cetera. like a head of a rich criminal organization

chillin' like a villian 

no one really knows what it means... but it rhymes.
Drew: Hey buddy wussup?

Alec: Nothin much, just chillin' like a villian

chillin like a villain

Dumbass saying that commercial advertisers ripped off as "Gelling like a felon"
If I see those faggy guys trying to be cool in that shoe sole commercial again, I'll scream!
chillin like a villain by 'YO MAMA' September 24, 2003