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23 skidoo has been described as "perhaps the first truly national fad expression..."
23 skidoo is an expression I learned working in vintage clothing, a field brimming with people who hoard weird facts and kitschy slang. This is the story they love to tell about its origin:
New York City's Flatiron Building, at 23rd and Broadway, had a shape that funneled wind. As a result, young men would loiter nearby in hopes the gusts would lift a skirt or two, and local police would chase them away with a cry of "23 skidoo!" (Skidoo was already a thing by then.)
It's bunk.
The Flatiron Building opened in 1902, but "twenty three" was noted as "get lost" slang by 1899, attributed to everything from Charles Dickens to circus gamblers to telegraph operators. Skidoo was (among other things) used to describe early automobiles--skidoo wagons--in print by 1904.
Around then, a musical called "Little Johnny Jones" opened in New York; it appeared in Los Angeles in 1906. One of the characters used "23" and "skidoo" together. (The writer, George M. Cohan, said he'd "heard it in San Francisco.") Somehow, that weird bit of slang tickled people. Soon "23 skidoo" was sweeping the nation, appearing on postcards and in advertisements.
But the Flatiron building had nothing to do with it, and if anyone tries to tell you different, you can tell 'em: 23 skidoo!