“What begins as a precise term can evolve into something contradictory, confusing, or even the opposite of its original intent,” writes CLIVE WILLIAMS, whose latest Whimsy column looks at “contranyms” – single words that can mean both one thing and its opposite depending on context.

“The trouble with words is you never know whose mouth they’ve been in.” –Dennis Potter

English is a language in constant flux, shaped by centuries of borrowing, cultural shifts and semantic drift. 

What begins as a precise term can evolve into something contradictory, confusing, or even the opposite of its original intent. 

This phenomenon is particularly evident in words whose meanings have inverted over time or in “contranyms” (also known as auto-antonyms) – single words that can mean both one thing and its opposite depending on context. 

Contranyms and contronyms are the same thing. They are also called Janus words after the two-faced Roman god.

I’ve explored a selection of such words, consistently tracing each from its original meaning (etymological root and earliest English usage) to its modern primary meaning, using sources such as the Oxford English Dictionary and Merriam-Webster.

Semantic shifts: words that flipped or diverged

Artificial

• Original meaning: Made by human skill or art (Latin artificialis, from artificium “craftsmanship”). Neutral or positive in early English (14th century), implying ingenuity.
• Modern meaning: Fake, synthetic, or not natural – a pejorative shift in the 18th–19th centuries with industrial connotations.

Awful

• Original meaning: Full of awe; inspiring reverence or wonder (Old English awe “fear” + full). Used positively or neutrally until the 18th century. 
• Modern meaning: Very bad, unpleasant, or dreadful – the awe-inspiring sense eroded, leaving only negativity by the early 19th century.

Disgruntled

• Original meaning: Made discontented or dissatisfied (intensive form of gruntle, a frequentative of grunt, implying grumbling; first as disgruntle in 1682).
• Modern meaning: Angry, irritated, or sulky. Notably, gruntle alone never meant “happy” in standard usage (though humorously revived in the 1920s as a back-formation, eg, “gruntled employee”); the word is inherently negative.

Egregious

• Original meaning: Outstandingly good or distinguished (Latin egregius “illustrious,” from ex grege “out of the herd”). Positive in English from the 16th century.
• Modern meaning: Outstandingly bad or flagrant – an ironic reversal by the 18th century.

Extraordinary

• Original meaning: “Outside the ordinary order of things” (Latin extra- “beyond” + ordinarius “orderly, regular,” from ordo “order”). Entered English in the 15th century (c. 1440) to denote something exceptional or beyond normal rules.
• Modern meaning: Remarkable, amazing or very unusual retaining the sense of exceptionality, though the prefix extra is now often mis-parsed as “more” (as in “extra cheese”), leading to etymological confusion.

Nice

• Original meaning: Foolish, ignorant, or stupid (Old French nice “silly,” from Latin nescius “ignorant”). Entered English in the 13th century with negative connotations.
• Modern meaning: Pleasant, agreeable, or kind – a gradual polite euphemism from the 18th century onward.

Nonplussed

• Original meaning: “No more can be said or done” (Latin non plus “not more”). First recorded in English in 1582 as a state of being utterly perplexed or at a loss.
• Modern meaning: So surprised or confused that one doesn’t know how to react – essentially unchanged, though sometimes misused to mean “unfazed.”

Regardless / Irregardless

• Original meaning: Regardless (c. 1590): Without regard or heed (from regard + -less). Irregardless (early 19th century, blend of irrespective and regardless): Intended as emphasis but creates a double negative (ir- “not” + regard + -less “without”).
• Modern meaning: Both mean “without regard” or “nevertheless.” Irregardless is nonstandard and often criticized as redundant, though accepted in informal speech for emphasis.

Sanction

• Original meaning: A binding decree or ordinance (Latin sanctio, from sancire “to make sacred/inviolable”). Could imply enforcement in either direction; in English (16th century), initially “authorise” or “ratify.”
• Modern meaning: Either “approve/permit” or “penalise/impose penalty” – a true auto-antonym, with both senses coexisting since the 18th century.

Silly

• Original meaning: Happy, blessed, or innocent (Old English sǣlig “blessed,” from Proto-Germanic sēligaz “happy”). Positive in Middle English.
• Modern meaning: Foolish or absurd – a downward shift via “innocent” to “simple-minded” by the 16th century.

Sophisticated

• Original meaning: Corrupted, adulterated, or made unnatural (from Medieval Latin sophisticare “to tamper with,” linked to sophistry). Pejorative in early English (17th century).
• Modern meaning: Polished, refined, or worldly – a positive shift in the 19th–20th centuries, especially in technology and culture.

Terrific

• Original meaning: Causing terror (Latin terrificus, from terrere “to frighten” + -ficus “making”). First in English c. 1660.
• Modern meaning: Wonderful, excellent, or impressively good – a 19th-century shift via “intense” to positive exaggeration.

Clive Williams is a Canberra columnist