I’ll take two Value Sprees and a small absinthe, please.
Dear Word Detective: I just cashed my paycheck and told the bank teller that I could now go out and “paint the town red.” Why would I say that? — Phil Norton.
Because you’re doing your patriotic duty as an American and spending every last dime you get so our national personal savings rate remains safely below zero? Or maybe you’re just tormenting me, knowing full well that if I set out to paint our little town red I’d have to settle for some really bad pizza and a gallon of Jolt from the Quickee-Mart.
To “paint the town red” means to celebrate flamboyantly and publicly, especially to go on a wild spree, usually involving multiple bars, restaurants and clubs plus copious quantities of alcohol. “Painting the town red” is, by definition, a group activity, requiring at least two people, and must be conducted in a spirit of giddy jubilation. One lonely guy on a crosstown bender is not “painting the town red.” Of course, alcohol is not strictly required. Lottery winners, for example, often “paint the town red” after their wins, sprinting from store to store and acquiring plasma TVs, cars, multiple pedigreed pets and scores of brand new distant cousins as they go.
The two questions that pop up when considering the phrase “paint the town red” are, of course, what it could possibly mean to “paint” in this sense, and why red in particular? The verb “to paint” is, as you would imagine, quite old, derived from the Latin “pingere,” meaning “to paint.” Interestingly, the noun “paint” arrived later than the verb (and was derived from it, in a process called “back formation”).
The original meaning in English of “to paint” was “to depict a subject using paint,” still a standard sense today. The “make that wall dark blue” sense of “to paint” came a bit later, but it’s that sense of “completely transform” we find in “paint the town red.” A band of celebrants “painting the town red” sets out to transform the humdrum with their excitement, to liven up every corner of the city, to make the locals sit up and take notice, to cast restraint to the wind and make the town theirs for a night with no worry about the morning after.
The first use of “paint the town red” in print found so far dates back to a New York Times article of 1883 (“Mr. James Hennessy offered a resolution that the entire body proceed forthwith to Newark and get drunk… Then the Democrats charged upon the street cars, and being wafted into Newark proceeded, to use their own metaphor, to ‘paint the town red’.”). Red does seem to have always been the color of choice, although Rudyard Kipling, in 1889, fussily specified “vermilion” (an shade of red with a hint of orange). James Joyce, in Ulysses (1922), differed slightly (“And there he was at the end of his tether after having often painted the town tolerably pink”), but stayed within the red spectrum.
So why red? It’s the color usually used to connote power, vitality and excitement (often with a hint of danger), all the features of a really good spree. And “painting the town blue” sounds like no fun at all.