twenty-three skidoo

While the phrase twenty-three skidoo, meaning to go away, to leave, is associated with 1920s, it is actually somewhat older, dating to the turn of the 20th century. And the constituent element are even somewhat older.

Twenty-three is the oldest portion of the phrase. From the Morning Herald (Kentucky) of 17 March 1899:

For some time past there has been going the rounds of the men about town the slang phrase “Twenty-three.” The meaning attached to it is to “move on,” “get out,” “goody-bye, glad you are gone,” “your move” and so on. To the initiated it is used with effect in a jocular manner.

How twenty three became associated with leaving is uncertain, but the above referenced article claims that it is a reference to Dickens’ 1859 A Tale of Two Cities. At end of the book, the hero, Sydney Carton, is going to the guillotine and is the twenty-third in line. The knitting-women watching the executions count off as each victim is beheaded:

Crash!—A head is held up, and the knitting-women who scarcely lifted their eyes to look at it a moment ago when it could think and speak, count One.
A second tumbril empties and moves on; the third comes up. Crash!—And the knitting-women, never faltering or pausing in their work, count Two.
[...]
She goes next before him—is gone; the knitting-women count Twenty-Two.
[...]
The murmuring of many voices, the upturning of many faces, the pressing on of many footsteps in the outskirts of the crowd, so that it swells forward in a mass, like one great heave of water, all flashes away. Twenty-Three.

Normally, one should be skeptical of such an explanation. But the appearance of the explanation so close to the appearance of the slang term makes it compelling.

Skidoo appears a few years later. The New York Times of 23 June 1901 records a yacht race in which a sloop name Skidoo participated. And the Los Angeles Times of 25 December 1904 has:

Skidoo for you, pal—get a live one.

Skidoo is also of uncertain origin, although many contend that it is a variant of skedaddle.

1906 is the big year for the combined phrase twenty-three skidoo. It appears numerous times in print during this year. This prank phone call is related in the Lincoln Daily Evening News (Nebraska) of 12 June 1906:

Night after night call would come on the heels of call.
“Is this 23?”
“Yes.”
“No, really? Well, skidoo for yours.”

And the Washington Post of 11 October 1906 has:

The members of the Thirteenth Minnesota Volunteer Infantry claim the credit for putting the “23 skidoo” sign on the hoodo generally supposed to follow the number “13.”

A common tale told about the origin is that it derives from the Flatiron Building on 23rd Street in New York. The odd shape of the building created updrafts that would lift women’s skirts as they walked past. Groups of young men would congregate to watch and would be chased off by police officers with the phrase twenty-three skidoo. A neat story, but one without a shred of evidence to support it. Not to mention that the building wasn’t even completed until 1902, after twenty-three was well established in the slang lexicon.

(Sources: Oxford English Dictionary, 2nd Edition; ADS-L; Barry Popik’s Big Apple Website)

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