saddest

ADJECTIVE

unhappy, depressed

Synonyms

STRONGEST

bitter dismal heartbroken melancholy mournful pessimistic somber sorrowful sorry wistful

WEAK

bereaved blue cheerless dejected despairing despondent disconsolate distressed doleful down down in dumps down in mouth downcast forlorn gloomy glum grief-stricken grieved heartsick heavyhearted hurting in doldrums in grief in the dumps languishing low low-spirited lugubrious morbid morose out of sorts pensive sick at heart troubled weeping woebegone

Antonyms

STRONGEST

cheerful glad good happy hopeful joyful nice pleasant

WEAK

fortunate great lucky

ADJECTIVE

unfortunate, distressing

Synonyms

STRONGEST

bad dark depressing dismal miserable moving pathetic pitiful poignant regrettable serious sorry tragic unhappy

WEAK

calamitous dejecting deplorable disastrous discomposing discouraging disheartening dispiriting dreary funereal grave grievous hapless heart-rending joyless lachrymose lamentable lugubrious melancholic oppressive pitiable saddening shabby tear-jerking tearful unsatisfactory upsetting wretched

Antonyms

STRONGEST

advantageous blessed bright cheerful encouraging fortunate glad good happy hopeful joyful light lucky pleasant right unaffecting worthwhile

WEAK

great

Example Sentences

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

Saddest of all, Karen rarely speaks any longer.

From The Wall Street Journal • Nov. 22, 2025

I don’t know if you’ve ever seen the movie “Spinal Tap,” but that’s where the title “The Saddest of All Keys” comes from.

From Seattle Times • Dec. 21, 2022

Once Bridgers signed Muna to her Saddest Factory Records label in 2021, their fortunes changed overnight.

From BBC • Nov. 9, 2022

In 2021, she signed them to Saddest Factory.

From Los Angeles Times • Jul. 22, 2022

Saddest of all are the bereaved wives and mothers.

From New York Times Current History; The European War, Vol 2, No. 2, May, 1915 April-September, 1915 by Various