Is “Cheekiest” a Scrabble word?

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Yes
CHEEKIEST
Valid in at least one Scrabble dictionary

Valid in these dictionaries

SOWPODS / CSW
Scrabble UK & International
Valid
TWL / NWL
Scrabble North America
Valid
Large English Dictionary
General English word list
Invalid

Meaning of Cheekiest

adjective
  1. 1.Impudent; impertinent; impertinently bold, often in a way that is regarded as endearing or amusing.

  2. 2.(of swimwear, underwear, etc.) tending to reveal the cheeks of the buttocks.

  3. 3.(Australian Aboriginal) Poisonous (of animals such as snakes), dangerous, cunning, violent, potent.

Synonyms: insolent, saucy