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According to Google's dictionary (and MacOS/iOS dictionary), egregious has the following definitions:

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I've seen words with multiple definitions, but not ones that are exact contradictions. Some references state that "remarkably good" is archaic - is it possible that the meaning of this word has changed over time to be the exact opposite of what it once meant?

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Please tell us which references you have consulted. –  cornbread ninja 麵包忍者 Jun 18 '12 at 18:41
Written using real IPA not faikcow spellows lyke yers, egregious is pronounced either /ɪˈɡriːdʒɪəs/ or /ɪˈɡriːdʒəs/. –  tchrist Jun 18 '12 at 23:32
It's a real bad word. –  Mark Beadles Jun 28 '12 at 20:48
It's an egregious word huh.. –  maq Jun 28 '12 at 21:26

4 Answers 4

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I found the following reference¹:

Bill Bryson is a more popular writer on the subject of language. Discussing changes in word meanings, Bryson writes:

Surprisingly often the meaning becomes its opposite or something very like it. Counterfeit once meant a legitimate copy. Brave once implied cowardice — as indeed bravado still does. (Both come from the same source as depraved). Crafty, now a disparaging term, originally was a word of praise, while enthusiasm, which is now a word of praise, was once a term of mild abuse. Zeal has lost its original pejorative sense, but zealot curiously has not. Garble once meant to sort out, not to mix up. A harlot was once a boy, and a girl in Chaucer's day was any young person, whether male or female. Manufacture, from the Latin root for hand, once signified something made by hand; it now means virtually the opposite. Politician was originally a sinister word (perhaps, on second thoughts, it still is), while obsequious and notorious simply meant flexible and famous. Simeon Potter notes that when James II first saw St. Paul's Cathedral he called it amusing, awful, and artificial, and meant that it was pleasing to look at, deserving of awe, and full of skilful artifice.

This drift of meaning, technically called catachresis, is as widespread as it is curious. Egregious once meant eminent or admirable. In the sixteenth century, for no reason we know of, it began to take on the opposite sense of badness and unworthiness (it is in this sense that Shakespeare employs it in Cymbeline) and has retained that sense since. Now, however, it seems that people are increasingly using it in the sense not of bad or shocking, but of simply being pointless and unconstructive.

According to Mario Pei, more than half of all words adopted into English from Latin now have meanings quite different from the original ones. A word that shows just how wide-ranging these changes can be is nice, which is first recorded in 1290 with the meaning of stupid and foolish. Seventy-five years later Chaucer was using it to mean lascivious and wanton. Then at various times over the next 400 years it came to mean extravagant, elegant, strange, slothful, unmanly, luxurious, modest, slight, precise, thin, shy, discriminating, dainty, and – by 1769 – pleasant and agreeable. The meaning shifted so frequently and radically that it is now often impossible to tell in what sense it was intended, as when Jane Austen wrote to a friend, ‘You scold me so much in a nice long letter ... which I have received from you.’

¹ Bill Bryson, Mother Tongue [London: Penguin, 1990], pp. 71-72

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Really interesting article. It really is amusing and interesting to see how words evolved. It seems like a process that can't be witnessed live, but something that mysteriously happens over time.. –  maq Jun 18 '12 at 20:45
Now I want to read this book! Thanks for the excerpt! –  Anup Jun 20 '12 at 8:51
Yes, it is a good choice. I have already ordered the book on Amazon. Least but not the least, if you have appreciated my answer, don't forget to upvote it. @Anup –  user19148 Jun 20 '12 at 8:59

The etymology of egregious is simple: e- from ex- meaning "out of," plus greg- or grex- meaning "herd." (The root greg- or grex- also developed into the English word gregarious). Egregious is applied to a number of things that stand out from the herd: it is used synonymously with extreme, extraordinary, and notorious. More rarely, it has been used as an etymologically-correct antonym to gregarious, meaning "asocial."

Back in the 16th century, egregious meant "remarkable for good quality; striking; distinguished." That sense disappeared, but not before egregious developed the (still current) sense "notorious; conspicuous for bad quality or taste."

Courtesy: word.com (M-W online newsletter)

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In fact, there is a term for words that have meanings that are opposites of one another: contronym or auto-antonym. That page gives a number of examples, although it doesn't include "egregious" (it's not a complete list).

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There are many examples of words which have changed from one usage to the opposite usage over time. Usually these start out as a literal usage, and develop the opposite usage as a result of being applied to an individual or group that gave the characteristic "a bad name".

For example, a "pedagogue" was once simply a teacher (greek: paidos "child" + agogos "to lead") and took on the meaning of "strict disciplinarian" as a result of certain practices once rather common in schools.

Expanding on the answer given by Fr0zenFyr, when the word was first coined, it was probably applied to those who stood out in a way that was admired; then, at some point, either those qualities became undesirable, or some notable person who was thought of as standing out from the crowd did something unpopular, or it became undesirable to stand out at all, or people starting paying more notice to those who stood out negatively rather than those who stood out positively, or... (the possibilities are endless, but it almost always end up to be some sort of social phenomenon).

If you feel like researching this more and really get to the bottom of it, your best bet would be to do some cross-referencing between literature and history, and see if you can root out any correlation between the change in meaning, and the prominent people and events at that point in time.

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