Attempts to resolve the Quandary:
1
After his saloonmates failed to cooperate, Lil' Big Shorty painted the town red by himself, in such an incorrigible manner that he riled the sheriff, to whom he seemed incapable of truckling.
(by Elijah Shiffer)
The Quandary for Friday, April 25, 2014 consisted of:
Challenge: use all four words together in one illustrative sentence.
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2
Krystol Shampain was an incorrigible freeloader, and it riled the manager at the local casino to the nth degree when she refused to truckle to his house rules as she painted the town red by drinking and dining at his establishment, always managing to hit the buffet line while toting a huge handbag filled with plastic containers, which she stuffed with food to take home.
(by wordgirl)