If you paint the town red, then you have a riotously, recklessly good time. But what does painting—and, for that matter, painting things red—have to do with what the Merriam-Webster Dictionary defines as “to go out drinking, dancing, etc.”?

Well, as always with these kinds of things, there are a number of etymological theories. But English folklore will have you believe that the phrase alludes to one drunken night, and one drunken aristocrat, in particular.

According to legend, at the root of painting the town red is Henry de la Poer Beresford. Despite being an Eton- and Oxford-educated aristocrat (he became the 3rd Marquess of Waterford after the death of his father in 1826) Beresford was a notorious hooligan, whose entry in the Oxford Dictionary of National Biography perfectly sums up his character:

"[Beresford] returned to Eton in 1838 to steal the headmaster’s whipping block, an exploit [he] celebrated with an annual dinner. He matriculated at Christ Church, Oxford, in 1829, but was invited to leave, and for the next decade he was to be found most frequently at the racetrack, on the hunting-field, or in the police courts. His favoured companions were young 'sporting men,' prize-fighters, and prostitutes; powerfully built, rich, and with an uncontrolled sense of humour, it amused him to challenge passers-by to fight him, to break windows, to upset (literally) apple carts … When, as frequently occurred, his activities landed him in court, he laughed at (and paid) the derisory fines which were designed to control the excesses of the working class, not those of the apparently limitlessly wealthy aristocracy."

In fact, Beresford’s extraordinary and seemingly unstoppable misbehavior even saw him considered a suspect in the unsolved case of Spring-Heeled Jack, an acrobatic fire-breathing reprobate who terrorized London in the late 1830s, half a century before Jack the Ripper. But Beresford’s bad behavior appears to have been more hedonistic than it was dangerous or anarchic—as evidenced by the night he and his friends spent in the sleepy Leicestershire countryside.

In the early hours of April 6, 1837, Beresford and a group of companions arrived at the tollgate of Melton Mowbray, a small town about 20 miles outside of Nottingham. After a day of gambling, hunting, and (all but non-stop) drinking at the Croxton Park races, Beresford and his crew were in typically boisterous form—and in no mood to be held up by a sleepy tollgate operator. Unfortunately for the operator, the gatehouse was in the midst of being repaired and alongside it were strewn workmen’s ladders, tools, and pots of paint. Seeing an opportunity for mischief, Beresford grabbed the paint and began daubing it over the tollgate (and, according to the story, the tollgate keeper himself). From there, he and his friends headed into town.

In the center of Melton Mowbray, Beresford’s riotous group continued their unruly rampage. The pub sign was torn down. The post office window was smashed. Gardens were trampled. A police constable who tried to intervene was knocked to the ground. And through it all, everything—walls, windows, doors, signposts, and even the policeman’s face and neck—were daubed in bright red paint.

The following morning, the people of Melton Mowbray were in an uproar. Beresford and his companions were promptly arrested and made to cover the cost of all repairs; eventually, they were charged with common assault, and fined an eye-watering £100 each (equivalent to more than $12,000 today). Beresford’s night of quite literally “painting the town red” had cost him dearly.

There’s no doubt that Beresford’s night of unruliness certainly took place: Records from the Derby Assizes document Beresford’s sentencing, and an article published in New Sporting Magazine in 1838 described a notorious “spree” that “took place in Melton Mowbray last season,” immortalized in an illustration by an artist named “Mr. R. Ackermann [of] 191 Regent Street.” In the picture, an unnamed group of gentlemen in scarlet-colored hunting jackets are depicted daubing paint on the sign of the local pub and attacking a police officer:

"Three gentlemen in scarlet coats, small-clothes, and silk stockings … are seen engaged in painting the sign of the White Swan red; and two others of the same class are perceived painting the window of the Post Office in the same manner. Another of those 'bloods' is making a stroke with his brush at the back of a flying watchman; two others, like regular gutter-bullies, are engaged in personal contest with two watchmen, and three MEN in scarlet have a single watchman down and are daubing his face with paint."

But as genuine as Beresford’s actions were, there’s a problem when it comes to connecting his paint-throwing night in Melton Mowbray with the origin of painting the town red: The expression did not appear in print until July 1883, almost half a century after Beresford’s night on the tiles. Not only that, but its earliest written record comes not from some local Leicestershire newspaper, but from The New York Times:

"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.'"

Could the events of April 6, 1837 really have inspired an expression that not only found its way across the Atlantic, but that no one sought to put in print for another 50 years? It seems unlikely—and instead, several more straightforward theories have been proposed.

Perhaps painting the town red alludes to the reddishness of a drinker’s face or nose, or else to blood spilled in drunken bar brawls or arguments? Perhaps it alludes to the bright red color of celebratory fireworks, or to revelers who stay up so late that they see in the dawn? Or perhaps it’s a reference to shady red light districts, or to the bleary red eyes of heavy drinkers or partiers? They’re all plausible theories. But until any further written evidence is unearthed, all we can presume is that the expression painting the town red first emerged in mid- to late 19th-century American slang, before steadily gaining wider currency elsewhere. And whether the Marquess of Beresford literally “painting a town red” is its true inspiration or not, it’s still a superb etymological side note.