The slang term “23 skidoo” refers to getting away quickly, often in the sense of getting out while the getting is good. Like a surprising number of colorful and intriguing slang terms, the origins of this phrase are not known. However, there are a number of interesting theories to explain the roots of 23 skidoo.
Although this term is associated with the Roaring '20s in the United States in the eyes of many people, it is in fact older. The first documented use of “23 skidoo” occurred in 1906, with the term only being popularized in the 1920s. Some people have theorized that the explosion of slang in the 1920s was related to a relaxation of social norms and morals, and this may have been why older slang terms such as 23 skidoo came into vogue.
Skidoo is itself a slang term which means “to leave quickly,” and it is a bit older than “23 skidoo.” Skidoo appears to be derived from “skedaddle,” a word which emerged in the Civil War. The origins of skedaddle are also clouded, adding to the mystery which surrounds the rise of 23 skidoo. Skidoo has also historically been used alone to mean “go away.”
One theory suggests that the term is a reference to the Flatiron Building, a notable New York landmark located on 23rd street. As visitors to the site today have noted, the peculiar shape of the building creates unusual air currents in the area, which sometimes have amusing effects on those walking by. In the early 1900s, women wore long skirts and rarely showed their ankles, and allegedly men would gather around the Flatiron to watch their skirts flip up in the breeze. Police were said to be giving men the “23 skidoo” when they dispersed the groups.
Others have suggested that the term may have originated in the West, during a prison break. The prisoners agreed that the signal for the escape would be a shout of “23 skidoo,” upon which they would scatter, hoping that a few men escaped in the subsequent confusion. Historians of racing point out that on many tracks, the 23rd horse would be forced to start behind the field, because there was only room for 22 horses to run side by side, so the 23rd horse would need to skidoo to get a chance of winning. This lead jockeys to say “23 skidoo for you” to the unlucky jockey seated on the 23rd horse.
All of these explanations for 23 skidoo are probably, unfortunately, folk etymology, with little basis in history. The origins of this term have likely been lost over time, to the dismay of some slang historians.