April 16, 1999

fly

With the popularity of the song "Pretty fly for a white guy," you've probably received numerous queries about 'fly' in that context. I've been told that it means 'cool' but I don't see any logical reason why that should be. Add me to the list of those who want to know where this comes from.

Others may have asked about fly before, but you are certainly the first one to cite the title of the Offspring song whilst doing so.

The word fly, as a slang adjective, has a number of senses, all of which are probably much older than you think, but unfortunately there is no convincing explanation for the semantic development of the earliest meaning.

The main original sense of fly was 'aware of what is going on; alterted; in the know', found since the early nineteenth century and chiefly a Briticism. A closely related sense is 'clever; artful; smart', which occurs in the early eighteenth century in an isolated Scots example, but otherwise appears to stem from our first sense and became common in the mid-nineteenth century. This sense was relatively common in the American underworld from the late nineteenth to early twentieth century but is now largely obsolete, though it persists in British use. Fly is usually thought to be derived from the verb fly, but exactly how or why is still debated.

Derived from this is our sense, or a sense very close to ours, found as far back as the 1870s, when the National Police Gazette wrote about "the young...men about town who think it is awfully 'fly' to know tow-headed actresses." This means 'stylish; sophisticated' but it ultimately gave rise to the slightly broader 'attractive; splendid; superlative; "cool"'. Chiefly Black English, it has been found in rap music from the earliest days of that genre, from which it has achieved a wider currency in mainstream usage.

Two other nuances, both around since the 1880s, are 'sexually free; wanton; being a prostitute', and 'insolent; audacious; brash'.

Some of the many derived words include fly-boy, which meant 'a shrewd or sophisticated fellow' decades before it referred to a male aviator; fly-cop 'a police detective'; and fly-girl, originally referring to prostitutes, though now meaning 'an attractive young woman'.