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A word originating from the Chicagoland area. "Headass" is used to Roast people of any decent.
"You man's is a headass bitch on foe nem."
Headass by willijay June 16, 2018
Boy 1: Boy if you don’t get to train track teeth faceass up outta here.
Boy 2: Shut yo expo marker built ass up.
Shut your my eyebrows connect like legos headass outta here.
Headass by iSnagThoseYT April 4, 2019
1) A term used at the end of a funny, insulting joke.

2) A term used to describe someone who is doing something nice and corny.
ex #1/ “ Shut yo ass up with your noodle headass.”

ex #2/ ex/“ Jay’s headass got us ankle bracelets <3.”
Headass by jordi147 June 16, 2019
When you accidentally misspell deadass and it creates quite the confusion confusion
This man: Dude this guy needs some milk, headass.
That guy: Dude, wtf 😂
Headass by warrobotsalt August 10, 2019
People that have a name starting with an A and ending with an E. They’re a whole headass and never speak true fax.
You’re a whole headass.
Headass by Yourmomsgae69 August 20, 2019