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Sorrowful, downcast
The man had a woebegone face.
woebegone by AlterLynx October 20, 2017
Related Words

webaganda 

Propaganda spread specifically via the internet, especially using low resolution images of a political nature often incorporating photo-montage.

(The term first popularized by a psychological warfare expert in 2005)
The distribution of mocking retouched photographs of US President George Bush portraying him as a buffoon or to ridicule US foreign policy, distributed via chain emails and posted on political internet forums, is an example of webaganda.
webaganda by Psywarrior January 1, 2009
A term used by Auburn fans in place of using the popular "war eagle"
Welcome to Auburn. Woeag
WOEAG by aubie2010 December 22, 2012

WoWbagger 

A computer-roleplaying-game player, whose character is such a high level that the playing is actually getting a bit boring. It can either mean a player who moves very slowly in the game, preferring to level up than follow the plot; a player who is stuck in the plot and wanders aimlessly trying to find a way to continue; or a player who has almost completed the plot, but doesn't want to game to end and is just wandering, unwilling to finish.
The term originates from the Douglas Adams's novel "Life, the Universe, and Everything", where an immortal grey-green alien by the name of Wowbagger the Infinitely Prolonged travels the universe in order to insult everybody in alphabetical order. Also, WoW stands for World of Warcraft, a large, popular multi-player online roleplaying game.
"Oh I don't play that game anymore, I became such a WoWbagger in it."
WoWbagger by ExapnoMapcase November 1, 2006
don't look so woebegone, Marshall
Woebegone by Rawwmatic June 28, 2018
A word used to express surprise, angst, disappointment, joy, excitement or scandal.

It is very multi-faceted, and if said in the right tone, can be used for any situation.
Pronounced: wuh-bag
Policeman: "sorry ma'am your cat has been runover"
You: "oh woobag!"

or

Girl: "omg i just slept with the hottest guy"
You: "woobag!"

or

Teacher: "Zac Effron will be visiting college tomorrow"
You: "WOOBAG!"
Woobag by lislee lislee November 17, 2009