woebegone

From Old English wābegān (“beset by woe”), from wā (“woe”) + begān (“to beset, to surround”)

• (UK) IPA^(key): /ˈwəʊbɪɡɒn/
• (US) enPR: wōʹbĭ-gän, IPA^(key): /ˈwoʊbɪɡɑn/

woebegone (comparative more woebegone, superlative most woebegone)

1. In a deplorable state.
2. Filled with or deeply affected by woe.
   • 1957, Jack Kerouac, On The Road‎

     When he was finished, as such, he was wringing wet, and now he had to edge and shimmy his way back, and with a most woebegone look, and everybody laughing, except the sad blond boy, and the Minnesotans roaring in the cab.

• (in a deplorable state): dilapidated, derelict, godforsaken, ramshackle, rundown, tumbledown
• (filled with woe): See Thesaurus:sad or Thesaurus:lamentable