‘Paint The Town Red’, Meaning & Context

The phrase “to paint the town red” refers to going out, perhaps drinking extravagantly, dancing, and indulging in other means of revelry. It connotes a night of uninhibited fun: an evening of loud amusement, mainly in cities full of bars, clubs, or other places where people come together socially. It carries the connotation of rendering an ordinary, possibly drab town into colourful and wild shades, like the dripping colours a painter would put onto a sheet of white canvas. It suggests carefree joy, with moments of wildness.

People say this when talking about nights of partying that were either planned or impromptu. For example, one might say, “After finishing their exams, the students decided to paint the town red.” While often associated with drinking and nightlife, the phrase can also be applied more broadly to any exuberant celebration. Despite its playful connotations, it may sometimes carry a hint of indulgence or excess, suggesting that the revellers may wake up with regrets.

Origin of Idiom ‘To Paint the Town Red’

The exact origins of “to paint the town red” are debated, but the most famous theory traces it to a raucous incident in 1837. The Marquis of Waterford, an Irish aristocrat notorious for his wild behaviour and his rowdy friends, reportedly caused havoc in the English town of Melton Mowbray. It ended with a wild night of rioting through the town, knocking over flower pots and breaking windows and, quite literally, painting doors and signs red. The legendary escapade became the source that tied the expression to wild celebration.

Another theory has the phrase coming from the late 19th-century American West. Following cowboys after very long drives into town, this would have been flooded with the cowboys blowing their pay on whiskey and gambles, mayhem, and riotous behaviour —”painting” the town red.

So the origin is unknown but the phrase reached popularity in the early 20th century and remains widely used today to describe any night of uninhibited revelry.

The Shakespeare Connection

Although the phrase “to paint the town red” does not appear in the works of Shakespeare, some scholars believe its imagery corresponds with his plays. Indeed, Shakespeare repeatedly used colours and metaphors with painting to explain emotions, deceptions, and excesses.

In Macbeth, for instance, blood becomes a symbol of guilt and violence, with Lady Macbeth exclaiming, “Who would have thought the old man to have had so much blood in him?”—a line that evokes the idea of staining or covering something in red.

Similarly, in The Taming of the Shrew, Petruchio speaks of altering Katherine’s behavior as if changing a painting, linking excess and transformation. While these examples do not directly lead to the idiom, they show a linguistic tradition of associating red with passion, revelry, and chaos. Shakespeare’s vivid use of imagery likely contributed to the later development of expressions like “to paint the town red.”

Paint the town red

Painting the Town Red in the Media

Music

The phrase “to paint the town red” has cropped up a lot in music, often representing celebration, partying, and wild nights. Many songs make use of the idiom for freedom, excitement, and indulgence.

Paint the Town Red by Doja Cat (2023) has the phrase for confidence and defying convention—very much taking the traditional meaning and adding to it a very modern, punk-like twist.

Other examples, like country and rock songs, really lean into the spirit of revelry inherent in the idiom. For instance, in the classic country song I’m Gonna Paint the Town by George Jones, the phrase is used to express a plan for drinking and partying to forget heartache. Similarly, in punk and rock music, the idiom often conveys themes of excess and rebellion, fitting the genre’s energetic nature.

From jazz to pop to rock, “painting the town red” is a powerful lyrical device that instantly conjures images of unrestrained fun and excitement.

Literature

The idiom “to paint the town red” has appeared in various literary works, often symbolizing wild revelry or reckless abandon. In F. Scott Fitzgerald’s The Great Gatsby, the lavish parties at Gatsby’s mansion reflect the spirit of the phrase, even if it is not used directly—characters indulge in extravagant celebrations that embody the idiom’s essence.

In On the Road by Jack Kerouac, Sal Paradise and Dean Moriarty frequently “paint the town red” as they embrace hedonistic adventures across America. The phrase also appears in modern crime fiction, where characters indulge in nights of excess that lead to unintended consequences.

Advertising

The idiom “to paint the town red” is used in advertising to convey excitement, celebration, and indulgence. Brands in the nightlife, entertainment, and luxury sectors often borrow from the phrase to suggest their products or services will lead to an exciting, unforgettable experience.

Alcohol and beverage companies often use the idiom to market their drinks as essential for a lively night out. For example, Smirnoff and Bacardi have incorporated variations of the phrase in campaigns promoting social drinking and partying.

Fashion and beauty brands also use it—cosmetic companies might advertise a bold red lipstick as a way to “paint the town red,” linking confidence and glamour to their products.

Additionally, travel and tourism campaigns, particularly for destinations known for nightlife, such as Las Vegas or Ibiza, use the idiom to attract visitors seeking adventure and fun.