woefullest

Adjective

woeful (comparative woefuller, superlative woefullest)

1. Full of woe; sorrowful; distressed with grief or calamity.
   • How many woeful widows left to bow / To sad disgrace!1595, Samuel Daniel, “(please specify the folio number)”, in The First Fowre Bookes of the Ciuile Wars between the Two Houses of Lancaster and Yorke, London: […] P[eter] Short for Simon Waterson...

   Synonyms:

   miserable, woe, atrabiliary, atrabilious, blitheless, dispirited, blue, bummed out, chapfallen, cheerless

2. Bringing calamity, distress, or affliction.
   • a woeful event

   Synonyms:

   calamitous, disastrous, apocalyptic, cataclysmal, cataclysmic, catastrophic, deadly, debacular, destructive, devastating

3. Lamentable, deplorable.
   • Thou seest we are not all alone unhappy:
     This wide and universal theatre
     Presents more woeful pageants than the scene
     Wherein we play in.c. 1598–1600 (date written), William Shakespeare, “As You Like It”, in Mr. William Shakespeares Comedies, Histories, & Tragedies […] (First Folio), London: […] Isaac Iaggard, and Ed[ward] Blount...

   Synonyms:

   rueful, woebegone, atrabiliary, atrabilious, deplorable, depressing, distressing, grievous, heartbreaking, heartrending

4. Wretched; paltry; poor.
   • What woful stuff this madrigal would be / In some starv'd hackney sonneteer or me!1711, Alexander Pope, An Essay on Criticism; republished in The Complete Poetical Works of Alexander Pope, Boston, New York: Houghton, Mifflin and Company, 1902, page 72

   Synonyms:

   inferior, shoddy, abject, filthy, base, beggarly, blameworthy, carrion, cheap, choical