[woh-bi-gawn, -gon]
beset with woe; affected by woe, especially in appearance.
showing or indicating woe: He always had a woebegone look on his face.

1300–50; Middle English wo begon orig., woe (has or had) surrounded (someone); wo woe + begon, past participle of begon, Old English begān to surround, besiege (see be-, go1)

woebegoneness, noun

2. suffering, troubled, forlorn, gloomy.
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World English Dictionary
woebegone (ˈwəʊbɪˌɡɒn)
1.  sorrowful or sad in appearance
2.  archaic afflicted with woe
[C14: from a phrase such as me is wo begon woe has beset me]

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
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Word Origin & History

c.1300, in me is wo bigone "woe has beset me," from begon "to beset, surround."
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
Redemption for the poem's woebegone mariner comes when he embraces all life, no
  matter how lowly.
Reasons and results couldn't be worse than the woebegone state of expression to
  which human discord has devolved.
Woebegone wooden houses, many of them falling down, dot the hillsides along the
The subtle and admittedly woebegone have been replaced by the dynamic and
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