One of the main reasons for the existence of slang is to keep the outsiders from understanding the insiders. Making up new words is one way to achieve this, but it’s not the only one. A favorite trick for the young to play on the old is to take an established word and completely change its connotations from bad to good. In recent decades we’ve seen sick, wicked, ill, and bad recruited to the “hearty positive endorsement” side. While some would lament the decline of language suggested by such wanton disregard for word meaning, this kind of meaning switch is nothing new. Here are 13 fine, upstanding words that long ago switched from negative to positive (or vice versa).

1. Fun

Fun was first a verb meaning "to cheat or hoax." It came from fon, an old word for "fool." It still retains some of that sense in “make fun of,” but now also means "a merry good time."

2. Fond

Fond also goes back to fon, and it once meant "foolish and weak-minded." It came to then mean over-affectionate in a negative, cloying way. Now it’s positive, but at root, being fond of something is basically being a fool for it.

3. Terrific

The root of terrific is terror, and it first meant terror-inducing. It then became an exaggerated intensifier (“terrifically good!” = so good it’s terrifying) and then a positive term all on its own.

4. Tremendous

Like terrific, tremendous has its roots in fear. Something tremendous was so terrible it caused trembling or shaking. It also became an intensifier (“tremendously good!”) before it went all the way positive.

5. Awe

According to the Oxford English Dictionary, awe originally referred to “immediate and active fear.” It then became associated with religious, reverential fear, and then to a feeling of being humbled at the sublime. While awful retains the negative sense, awesome took on the positive one.

6. Grin

To grin was to bare the teeth in a threatening display of anger or pain. It then became the term for a forced, fake smile, before settling into an expression of happiness.

7. Smart

Smart was first used in Old English to describe things that cause pain. Weapons, nails, and darts were smart. Shakespeare’s Henry VI has the phrase “as smart as lizards’ stings.” It took on connotations of sharpness, quickness, intensity, and, through smart, pain-causing words or wit came to stand for quick intelligence and fashionableness.

8. Egregious

Egregious was a positive word that turned negative. It used to mean "eminent and distinguished," but because people started using it sarcastically, it came to mean "bad and offensive."

9. Sad

Sad started with the meaning of "satisfied or sated," also sometimes "steadfast" or "firm." It then went from meaning "serious," to "grave," to "sorrowful."

10. Smug

Smug first meant "crisp, tidy, and presentable." A well-dressed person was smug in this way, and it later came to mean "self-satisfied and conceited."

11. Devious

Devious comes from de via, "off the way." It once meant "distant" or "off the road." It took on the meaning of wandering—there were devious comets, devious minnows—and, because to do wrong was to stray from the right path, it eventually came to mean "scheming and deceitful."

12. Facetious

To be facetious was once to have elegant, gracious, high style, and to be jokey and witty. It came from a Latin term for playful humorousness. It is still connected with a type of humor, but with an unproductive or annoying connotation.

13. Bully

Bully used to be a term of endearment for men or women. A bully could be a good friend or a sweetheart. It then came to stand for a swaggering braggart and than a coward who picks on others.

This list was first published in 2015 and republished in 2019.