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*wastrel \WAY-struhl\ (noun) –
1 : A person who wastes, especially one who squanders money; a spendthrift.
2 : An idler; a loafer; a good-for-nothing.
"When I was a student in Lawrence, Kansas, there was a wastrel in the town who pretended to have been a pal of Ulysses Grant, the President. This wastrel was always hanging round the bar of the Eldridge House, or some other saloon, and if he had ever met you in any company always called you afterwards by your Christian name and proposed a drink." — Frank Harris, ‘My Life and Loves’
Wastrel is from waste + -rel (as in scoundrel).

\WOE-bee-gon\ (adjective) –
1 : Beset or overwhelmed with woe; immersed in grief or sorrow; woeful.
2 : Being in a sorry condition; dismal-looking; dilapidated; run-down.
"When the lunch bell rang the woebegone employees all trudged joylessly to the cafeteria for their tasteless sustenence."
Woebegone is from Middle English wo begon, from wo (from Old English wa, used to express grief) + begon, past participle of begon, "to go about, to beset," from Old English began, bigan, from bi-, "around, about" + gan, "to go."