cheekiest

Adjective

cheeky (comparative cheekier, superlative cheekiest)

1. (informal) Impudent; impertinent; impertinently bold, often in a way that is regarded as endearing or amusing.
   • 'Shut up,' said Harrison. 'You chaps always behave as if you were jawin' us when we come to jaw you.' / 'You're a lot too cheeky,' said Craye.1899 February, Rudyard Kipling, “The Impressionists”, in Stalky & Co., London: Macmillan & Co., published 1899, →OCLC, page 112
2. (informal, usually, underwear) Tending to expose the cheeks of the buttocks.
   • Barry said he introduced the cheeky bikini to the Coast three years ago: "I took a theatrical garment worn for as long as there have been strippers and showgirls — the G-string — and put it on the beach and gave it a name and we sold a heap."1984, Hugh Lunn, Queenslanders, page 159
3. (Australian Aboriginal) Poisonous (of animals such as snakes), dangerous, cunning, violent, potent.
   • A death adder is cheeky, a tree snake quiet. Wasps are only cheeky if you hold them in your hand.1994, Victoria Katherine Burbank, Fighting Women: Anger and Aggression in Aboriginal Australia, Univ of California Press, →ISBN, page 57
4. (Commonwealth, UK, informal) Indulged in as a treat, especially an unhealthy one.
   • Although sometimes I'd award myself a cheeky McDonald's hangover treat if I did well.2009, Amy Huberman, Hello, Heartbreak, Penguin UK, →ISBN