James Crockett, who has only been out of the county jail a short while, was likewise complimented for “ painting the town red,” and he is also visiting out of the city. Tommy Price, an ex-convict, left Owenton because the boys about town took him to the woods and flogged him. The earliest instance that I have found is from one of the unconnected paragraphs making up the column The Commonwealth, in The Courier-Journal (Louisville, Kentucky) of 3 rd November 1881: Of American-English origin, the colloquial phrase to paint the town red means to enjoy oneself flamboyantly, to go on a boisterous or exuberant spree.
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