Usually means: Inflicting the greatest pain possible.
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We found 11 dictionaries that define the word cruelest:

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

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

(Note: See cruel as well.)

Definitions from Wiktionary (cruel)

adjective:  Intentionally causing or reveling in pain and suffering; merciless, heartless.
adjective:  Harsh; severe.
adjective:  (slang) Cool; awesome; neat.
adverb:  (nonstandard) To a great degree; terribly.
verb:  (chiefly Australia, New Zealand) To spoil or ruin (one's chance of success)
verb:  (Australia, ambitransitive) To violently provoke (a child) in the belief that this will make them more assertive.
noun:  Alternative form of crewel. [Worsted yarn, slackly twisted, used for embroidery.]
▸ Also see cruel


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