Fly flea in a flue?

Dear Word Detective: In 1902, two Tin Pan Alley songwriters, Vincent Bryan and Harry Von Tilzer, wrote a song titled, “You Couldn’t Hardly Notice It At All.” The first two lines are, “A maid came in from Olean, she was a little shy, but you couldn’t hardly notice it at all. She met a gay young city chap, who tho’t that he was fly, but you couldn’t hardly notice it at all.” The maid goes on to snooker the gay young chap. In 1911 Nat D. Ayer and Paul West wrote “The Gum Shoe Man.” The first two lines are, “If you ever do wrong as you go along, there’ll be someone after you. He’s a man who’s fly with an eagle eye and he always spots a clue. He’s the Gum Shoe Man, and he always gets his man.” It seems as though, back in the early 1900’s, “being fly” was a term that meant something like being clever, astute, observant, not easily fooled. Do you know the origin and meaning of being “fly”? — Bob W.

Ah, those were the days, my friend. The days when a tune was a tune, only a bird was a loon, and gumshoe men kept the rabble in check. Or so I was told as a sprat, usually by the same cranky people who wouldn’t let me play with their plastic lawn flamingos. Where are they now? The flamingos, I mean. The cranks are still around, although their yards are now decorated with strange, angry signs. Incidentally, a “gumshoe man” back then was a detective, so-called because they were said to wear noiseless rubber-soled shoes, all the better to sneak up on miscreants.

Before we tackle “fly,” it’s worth noting that the lyrics you quote employ “gay” in the antiquated sense of “finely or showily dressed” common at that time, although the same word during that period also carried connotations of a frivolous or hedonistic nature. The word “gay,” from the Old French “gai” meaning “happy, carefree” (but also “frivolous” and “lewd”), has had dozens of meanings since it first appeared in English in the 14th century, so a complete history is beyond the scope of this particular column, but I’ll get around to it someday soon.

Your translation of “fly” in lyrics from the early 20th century as meaning “clever, astute, observant, not easily fooled” is right on the money. The adjective “fly” first appeared in slang with this sense of “sharp” or “in the know” in the early 19th century (“The rattling cove is fly; the coachman knows what we are about,” 1811); later in the century it also came to mean “dexterous, nimble” (“We’ll knap a fogle with fingers fly,” 1839). The “in the know” usage, which was originally largely confined to the criminal underworld, percolated out into general slang in the mid-19th century with the meaning of “smart, fashionable” and eventually “excellent, cool, attractive.” This sense took root in African-American slang in the mid-20th century, and was very common in rap and hip-hop culture starting in the 1980s or so.

Just where this use of “fly” as an adjective came from is a bit of a mystery. Most authorities regard it as most likely connected in some way to the verb “to fly” (from the Old English “fleogan,” from an Indo-European root meaning “to float or fly”), but no one has ever come up with a plausible explanation of the connection. (The noun “fly” originally meant simply “insect with wings,” and was applied to any insect that could fly, such as the butterfly.)

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