Usually means: Most irritable, bad-tempered, and moody.
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We found 12 dictionaries that define the word grumpiest:

General (10 matching dictionaries)
  1. grumpiest: Merriam-Webster
  2. grumpiest: Oxford Learner's Dictionaries
  3. grumpiest: Collins English Dictionary
  4. grumpiest: Vocabulary.com
  5. Grumpiest, grumpiest: Wordnik
  6. grumpiest: Cambridge Advanced Learner's Dictionary
  7. grumpiest: Wiktionary
  8. grumpiest: Dictionary.com
  9. grumpiest: Cambridge Essential American English Dictionary
  10. grumpiest: TheFreeDictionary.com

Business (1 matching dictionary)
  1. grumpiest: Legal dictionary

Slang (1 matching dictionary)
  1. Grumpiest: Urban Dictionary

(Note: See grumpy as well.)

Definitions from Wiktionary (grumpy)

adjective:  Dissatisfied and irritable.
noun:  (informal) A dissatisfied and irritable person.
▸ Also see grumpy

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