What does headass mean?
Headass is a mild insult for someone acting foolishly, ignorantly, ridiculously, or ineptly. Headass is also used as an adjective or interjection, and sometimes as a verb.
Examples of headass
… when I find out all the cheese slid off the pizza cause headass doesn’t know how to carry the box.
—@Cindy046, X (formerly Twitter), 1 Apr. 2017
yo i straight up do not endorse this headass eating sushi with a fork.
—@myunclesmemes, X, (formerly Twitter), 10 Oct. 2017
Last month, a woman was arrested for coughing on $35,000 worth of groceries. … Like god damn, if there was ever a time to cool it on the headass behavior, it’s right now.
—Joe Jurado, The Root, 9 Apr. 2020
Janine and Gregory burst into the teacher’s lounge, excited for their coworkers to bask in the sheer creativity of their costumes, only to be met by confusion and mockery. At first, they think it’s an implementation problem, swapping positions with each other as if making sense of an “I’m with Stupid” t-shirt. But the teasing continues, and Ava goes as far as calling them a “headass couple doing headass things” while updating the Urban Dictionary page for headass to a picture of them in their costume (also, thank you, Jacob, for white-splaining the word headass).
—Ile-Ife Okantah, “Abbott Elementary Recap: Headass Halloween,” Vulture, 30 Oct. 2024
If we’re being honest there’s a lot of brands/internet personalities that have gained mass followings by being a caricature of Black Twitter – basically digital blackface. Fleek, Bae, multiple dance trends, were all poorly co-opted by brands who erased the visibility and ingenuity of black content creators while making money. Gro0o0oss. Like, someone tell these advertisers how headass they look saying their chicken nuggets are “Nae-Nae-licious.”
—Jaboukie Young-White, quoted in Vulture, 16 Sept. 2016
Where does headass come from?
The adverb ass is frequently used after another word, as an intensifier, in order to give it more emphasis ("Wow! Those are some fancy-ass pants!"). The noun ass is also often combined with a preceding word, as in “don’t be a smart-ass.” Headass originated in African American English, and the earliest records of its online use date to the late 2000s.
Headass is a funny word, though. I mean, the word itself was not just funny upon first impression; It was familiar. It comes from the roasting tradition of punctuating a litany with “ass” or “lookin’ ass.”
—Lex Vee, Medium, 7 Apr. 2018
How is headass used?
Headass is often used somewhat humorously.
She took out her phone, opened Snapchat, and scrolled through her saved pics and videos: people hitting multiple Juuls simultaneously, her friends in dramatic poses with deadpan expressions and Juuls in their mouths. I burst out laughing at one captioned “100% Headass.”
—Jia Tolentino, The New Yorker, 14 May 2018
It can also be used, like plain old ass itself (as in “get your ass over here”), in emphatic reference to a specific person.
i gotta pay another twenty five dollars cuz yo gray’s lake headass don’t know how to talk to kids!
—Kristiana Rae Colón, “Suspension,” The Long Term: Resisting Life Sentences, Working Toward Freedom, 2018
Headass is also branching out and developing additional forms as a nouns, verbs, etc.
Who knew that old-ass Headass was capable of even greater feats of headassery?
—Jamel Brinkley, Witness: Stories, 2023
Instead of headassing trying to compare support for Blade to Black Panther we could be reflecting on Wesley Snipes interview about his attempt to make a Black Panther movie in the 90s that was stifled by industry BS and reworked into the first Blade movie
—@DecolonialBlack, X (formerly Twitter), 31 Jan. 2018