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.
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 3rd November 1881:
Tommy Price, an ex-convict, left Owenton because the boys about town took him to the woods and flogged him. 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.
The second-earliest occurrence of the phrase that I have found from Legislative Primer, a satirical dialogue published in The Weekly Register (Point Pleasant, West Virginia) of 18th January 1882:
Papa, what is this?
This, my boy, is a West Virginia Legislator.
Is it alive?
Well, slightly; its [sic] about the liveliest creature you ever saw when it is invited to take a little Mountain Dew.
Well, what is Mountain Dew, papa?
Mountain Dew, my boy, is the liquid representative of a fiery furnace; it is the elixir of a West Virginia Legislator’s life; he would rather do without his dinner than his Mountain Dew, and whenever he wants to paint the town red or paralyze things by making a flowery speech, he gets gloriously full of Mountain Dew.
Do these men paint the town red and make flowery speeches very often?
More frequently than seldom.
My hypothesis is that the phrase originated in the image of a torchlit procession or/and of a firework display that illuminate(s) a town. The two following passages support this hypothesis:
the large crowd in waiting became hilarious, and it was proposed to “paint the town red” by means of a torchlight procession.
– On 16th November 1884, The Daily American (Nashville, Tennessee) reported:
Bells, Tenn., Nov. 15.—The Democrats of Crockett County […] had a splendid procession, cannonade and painted the town red with fireworks, and shouted themselves hoarse.
This allusion to festive lights illuminating a town was perhaps reinforced by the connotations of energy and excitement attached to the colour red, as exemplified by the beginning of Painting it Red, published in The Wheeling Daily intelligencer (Wheeling, West Virginia) of 8th September 1884:
A citizen who was waiting at the corner of Jefferson avenue and Wayne street yesterday was accosted by a man about 27 years old, who said he wanted a little information. When told to drive ahead he asked:
“Almost every paper I pick up has something in it about somebody painting the town red. I don’t see any red around Detroit to speak of. Do they paint the buildings, or sidewalks, or what?
“My innocent friend,” replied the citizen, “the term does not refer exactly to paint and brushes. If you should come in here to clean out Detroit, or if you were going on a high spree, or if you intended to raise an excitement, you would slant your hat over your left ear, spit over your right shoulder, and announce in a loud voice that you were going to paint the town red.”
“Because red is the color of blood—fire—lightning—red-hot times, eh?
“Kind of a figgerative expression?”
The original allusion may also have been reinforced by the use of the verb paint in the sense of to drink. This particular use of paint is first recorded in Digby Grand: An Autobiography (London, 1853), by the Scottish novelist and poet George John Whyte-Melville (1821-78); the narrator has just met Squire Sauley, “a real Yankee character”:
The day was hot, and my new acquaintance, as he expressed it, ‘a thirsty crittur;’ so each hotel we passed on our pilgrimage called forth the same observation, ‘I guess I shall go in and paint.’ Three times we ‘painted’ accordingly.
Very early, numerous attempts were made to explain the phrase to paint the town red.
The following explanation first appeared in the Harrisburg Telegraph (Harrisburg, Pennsylvania) of 12th November 1884 (various newspapers later reprinted it):
Painting the Town Red.
How the Expression Originated—An Advance Agent Responsible.
“How is politics in Harrisburg?” asked Billy Welsh, the minstrel manager, of a Telegraph reporter, yesterday.
“Red hot during the campaign,” answered the reporter; “both parties have painted the town red.”
Mr. Welsh smiled and remarked: “That’s an odd expression—painting the town red—do you know where it originated?”
“No, but I would like to,” said the reporter.
“Well, I’ll tell you. On my last tour through the country with Callender’s minstrels—a year ago or more—I had as advance agent a man named Campbell, now with Coles’ circus in the South. Campbell was a genius at advertising, and never permitted a rival to get ahead of him. One day in Buffalo I called him up and said: ‘Campbell, I hear that Barlow & Wilson are covering my bills with their paper; I want that stopped.’ In an instant he was all excitement. ‘Where do I run across them?’ he asked. I told him he would strike them at Adrian, Michigan. Campbell went to the Courier printing house, and when next I saw him he had huge bundles of bills ready for shipment to Adrian. All were printed in bright red. ‘What are you going to do?’ I asked. ‘What am I going to do? I am going up to Adrian to paste these bills over Barlow & Wilson’s and on every dead wall in that place. I am going to paint the town red,’ and he left. When we got to Adrian it looked as if it was on fire, so thoroughly had Campbell done his work. That expression ‘painting the town red’ was so comic that the colored minstrels caught on to it, and whenever there was any excitement, or anybody got particularly loud, they always said somebody was ‘painting the town red.’ Of course it spread, and is now in use by everybody.”
However, I have searched in vain for a mention of this incident in the U.S. newspapers from 1884 and preceding years; moreover, Callender’s minstrels do not even seem to have performed during that period at Adrian, Michigan.
Thomas MacDonald Waller (1839-1924) was the 51st Governor of Connecticut (3rd January 1883–8th January 1885). According to The Wilson Advance (Wilson, North Carolina) of 5th December 1884, he coined the phrase to paint the town red:
Nearly every man you meet claims to have originated the expression “paint the town red.” The Danbury “News” says, The expression, “painting the town red,” signifying a jubilee, originated with Gov. Waller, who, in a congratulatory speech at a Yale boat crew victory, said: “I hope, gentlemen, you will paint this town red.”
This does not explain the origin of the phrase, but merely—and purportedly—identifies its alleged first user.
Additionally—and actually—Governor Waller could not have coined the phrase, since he made the speech in question on 28th June 1883, nearly two years after the earliest attestation of to paint the town red. A record of that speech was published two days later, on 30th June 1883, in the Morning Herald and Courier (New Haven, Connecticut); Governor Waller was in fact congratulating the Harvard (Massachusetts) boat crew, who had won the contest over Yale (Connecticut), and was not telling them to paint the town red, but was asking them not to:
“I hope you will not, as some say you intend, paint the whole town red. It would, I fear, damage the æsthetic reputation of your venerable college.”
It is most improbable that the following undated story, limited to a restricted area of Stratford, Connecticut, and involving a few persons only, gave rise to the phrase. That story appeared as follows in The Chicago Daily Tribune (Chicago, Illinois) of 6th December 1884:
ORIGIN OF “PAINTING THE TOWN RED.”
Letter from Stratford, Conn.: The origin of the term “painting the town red,” which has been used extensively throughout the State during the last campaign, is attributed to Gov. Thomas M. Waller. Again it is claimed by Billy Welsh, the minstrel manager, as having been ﬁrst used by his advance man out West after having literally besmeared a city with big handbills printed in red. When called to account for wasting the posters, the agent said he was bound to “paint the town red.”
Residents of Old Stratford remember Uncle Elnathan Wheeler, who formerly lived up the ferry road. When he was a boy nearly every other house in town was painted with the old-fashioned mineral red paint, more durable than any that is made nowadays. Having bought a large quantity of the paint at what was considered a low price, Uncle Elnathan tried to induce Harvey Hammond, who lived nearly opposit [sic], to enter into partnership, the two to “paint the town red,” meaning that at the very low ﬁgure nearly every one in town could be induced to “paint up.”
No evidence supports the following theory, which a person signing themself ‘Johannes Factotum’ put forward in a letter published in The Daily Inter Ocean (Chicago, Illinois) of 10th January 1885:
The truth is the first use ever seen of the expression was on the far frontier, and gave it a very sanguinary meaning. A set of bullies armed to the teeth came into a settlement in search of “gore,” and threatened with pistol and bowie knife to paint the town red before the next morning. In later days it has assumed a more peaceful rendering, and describes a place given over wholly to festivities, as if the town itself had assumed a roseate hue. The reference to persons in our cities who start out to “paint the town red” grows out of a misunderstanding of the origin of the slang expression.
On 14th January 1885, the same newspaper, The Daily Inter Ocean, published a response to Johannes Factotum’s letter, in which one Henry S. Mercer traced the phrase to two plays by the English poet and dramatist William Shakespeare (1564-1616)—the least that can be said about this connexion is that it is far-fetched:
PAINTING THE TOWN RED.
To the Editor of The Inter Ocean.
Chicago, Jan. 10.—In your issue of this day your correspondent, “Johannes Factotum,” gives a short history of the use and meaning of the above phrase; but can we not go back a little further and trace it to the immortal William?
In “A Winter’s Tale,” act 4, scene 3, we find Florizel saying:
See, your guests approach:
Address yourself to entertain them sprightly,
And let’s be red with mirth.
Again, in “King Henry the Fourth,” act 2, scene 4, Prince Henry says:
They call drinking deep, dying scarlet.
Henry S. Mercer.
Johannes Factotum dismissed Henry S. Mercer’s explanation in a letter published in the same newspaper on 15th January 1885:
I am unwilling to recognize the correctness of Mr. Henry S. Mercer’s suggestion in your issue of Jan. 14, regarding the origin of “painting the town red.” The expression was launched upon the world by a frontier newspaper man, who probably never read a line of Shakespeare in his life. It first had reference to sanguinary incursions of lawless border men, and therefor could not have sprung from “the immoral [sic] William,” in that sense at least. The application of it, following the election of Mr. Cleveland, arose, as I stated, from a misconception of the meaning of the term. If we were to search antiquity for the origin of “painting the town red,” why not go back of Shakespeare’s time, many years, when it was the custom to paint ale-houses red; and to the Red-letter Days, which were convivally [sic] observed, and which were marked in the almanacs with red ink?
Although the following explanation is based on the image of a fire illuminating a landscape, races that took place in the 1850s are unlikely to be the origin of a phrase that appeared in 1881 only; this is from The Davenport Democrat (Davenport, Iowa) of 25th October 1886:
The origin of the phrase, “paint it red,” is placed on Mississippi river steamboat men. It is said that back in the 50s racing was one of the exciting features of Mississippi river travel, and when an opportunity offered for a trial of speed all hands were breathless with excitement. The first command from the captain would be: “Paint her red, boys!” which was river slang for filling the fire-box with resin in order to create a quick, hot fire, at which time the fire-boxes would be thrown open. Then, if the night were dark, the effect was simply grand. As far ahead as the eye could see the river would be a deep red from the reflection, forming a most beautiful picture, which once seen could never be forgotten. It was at that time that the expression, “Paint the town red,” originated, as the old steamboat men intended to convey the idea by its use that they would have a beautiful time on arrival at their destination.
According to B. A. Phythian in A Concise Dictionary of Phrase and Fable (Hodder & Stoughton, 1993), the most probable origin of the phrase is
an actual piece of drunken vandalism by the Marquis of Waterford and a bunch of his chums who, as an aristocratic joke, actually painted parts of the local town red in the area of Melton Mowbray, Leicestershire, in 1837. The incident created sufficient stir to be recorded in contemporary verse and engraving.
However, it is difficult to explain how an event that took place in England in 1837 can be the origin of a phrase that appeared in the USA forty-four years later.
The following picture depicts that “piece of vandalism”:
Spree at Melton Mowbray.
Larking at the Grantham Toll-Gate.
Or Coming in for the Brush.
A Society of Distinguished Painters,
Who Hunt with Fox Hounds, Live Splendidly and only Paint at Night.
They left no man’s Sign, Name, or Calling
Untouched by something most appalling.
date: unknown – by Henry Thomas Alken (1785-1851)