I guess “above the fold” isn’t likely to catch on at this point.

Dear Word Detective: As part of my cancer treatment, my doctors are monitoring several blood levels for evidence that the chemotherapy is working. Recently, I experienced a significant drop in two of them — a very good sign. One of my doctors, in fact, referred to the results as “outstanding,” which led me to wonder: has the word “outstanding” always had positive connotations? It seems, based on the construction of the word itself, that you could interpret “outstanding” as “a significant outlier when compared to normal.” This suggests that something could also be outstandingly bad. Was it ever used this way? I wonder similar things about other words we use to connote “particularly good,” such as “exceptional.” — Fernando.

That’s a interesting question (and congratulations, of course, on your good news). As for “outstanding,” I’m starting to think that at some point I left my mental attic door open, because when I read your question I immediately flashed on a coffee mug someone in my family gave me back in the 1980s. It bore a cartoon (by Sandra Boynton, I believe) of a puzzled-looking cow surrounded by daisies, beneath which the caption read “To someone outstanding in their field.” So here’s a word, “outstanding,” that I probably read fifty times a day in various contexts, and have used in various senses myself zillions of times in the past thirty years, but when I start to consider the word I come up with a mental image of a perplexed cow. I’m not sure this is helpful.

“Outstanding” is a fairly old word, first found in print (so far) in 1611, and it has developed, as old words are wont to do, several meanings over the years. Speaking of which, isn’t it interesting that words never retire, or rust, or fall apart into a heap of useless letters at some point? We might call certain words “antiquated,” but they’re still usable, unlike a certain Ford I bought back in the late 90s.

When “outstanding” first appeared it was a simple combination of “out” and “standing,” drawn from the phrasal verb “to stand out,” which had appeared around 1540 in the sense “to jut out, protrude.” The initial meaning of “outstanding” was “jutting out, projecting or prominent” in a literal, physical sense (“Those who prefer supple and clinging fabrics to those which are stiff and outstanding,” 1896). But within about 20 years it had also come into use in a figurative sense meaning “continuing to exist or remaining to be dealt with,” especially describing a debt still owed or a legal matter yet unsettled, a sense still widely used today (“Cossiga asked De Mita to stay on to handle outstanding business,” 1989).

It wasn’t until the early 19th century that “outstanding” came to be used in its current general sense of “noteworthy,” “conspicuous” or “prominent” (“There are many interesting articles .. but there is hardly one of outstanding importance,” 1889). This was a largely value-free use of the word; a politician could be noted for his “outstanding” acts of corruption as well as his “outstanding” service to the public. To be “outstanding,” all a person or thing had to do was to draw special attention by “standing out” from the crowd. In this sense, Al Capone was an “outstanding” resident of Chicago. But that example is only (somewhat) funny because we now usually use “outstanding” to mean “outstandingly good.”

It’s difficult to pin down exactly when this neutral “standing out” connotation of “outstanding” gave way to the meaning “exceptionally good,” as the Oxford English Dictionary (OED) defines the sense. The earliest citation the current edition of the OED provides that clearly invokes this positive sense is from 1936 (“Your lawn tennis was outstanding; you were a magnificent boxer”), but the previous edition (1989) of the OED doesn’t list this positive sense at all. If I had to guess (and I guess I do) when the transition took place, I’d venture that it was a gradual process that really got going in the mid-20th century and spread through the mass media, particularly television advertising. The same shift of meaning, as you note, has affected “exceptional” as well as “remarkable,” both of which originally meant simply “not in the normal run of things” but now connote something more than likely to also warrant the adjectives “new,” “improved,” and “must-have.”