What does cheekiest mean?
'Cheekiest' is the superlative of the adjective 'cheeky', describing the highest degree of impudent boldness or irreverent playfulness. A person who is the cheekiest in a group is the one most likely to make sly remarks, flout small rules, or take liberties that others would not dare to take, yet usually in a way that amuses rather than offends. The word can also apply to actions or things, such as a steep price rise or a daring tactical move that shows remarkable audacity. Strongly associated with British English, where 'cheek' as a quality is often regarded affectionately, the term belongs to informal register and carries a warm, teasing connotation rather than a hostile one. It derives ultimately from 'cheek', the side of the face, which came figuratively to mean impudent self-assurance.
adjective (superlative of 'cheeky')The superlative form of 'cheeky': most impudently bold or irreverently playful in a way that is often amusing rather than seriously offensive.
- Most impudently bold or irreverent in a playfully disrespectful way.
- (Of a thing, such as a price or a move) most audaciously presumptuous or unreasonably bold.
"Even by his standards, that was the cheekiest remark he'd ever made to the headmaster."
"She flashed the cheekiest grin as she swiped the last biscuit from the tin."
"Charging five pounds for a cup of tea has to be the cheekiest pricing I've seen all year."
Calling someone the 'cheekiest' person alive is technically an insult delivered with a wink — it's one of English's few superlatives you can use as a compliment.
Reviewed by Deb Chak, Editor. AI-assisted content curated by RJS Tech Solutions LLP.
Etymology of cheekiest
'Cheekiest' derives from 'cheeky', an adjective formed in the early nineteenth century from the noun 'cheek'. 'Cheek' itself comes from Old English 'cēace', meaning the side of the face or jaw, and is related to similar Germanic forms. By the mid-nineteenth century, 'cheek' had acquired the figurative sense of impudent assurance or effrontery, giving rise to 'cheeky' and its comparative and superlative forms.
Word family
Usage notes
The word carries an affectionate connotation, especially in British English, where 'cheeky' behavior is often seen as charming rather than offensive. It is informal and best avoided in formal writing. As a superlative, it implies comparison among three or more things or an absolute extreme.
Don't confuse with
'Checkered' describes a pattern of squares or a history marked by alternating good and bad episodes, whereas 'cheekiest' means most boldly impertinent.