It’s by no means rare for words to rework and reshape themselves over time, to the extent that they can end up with vastly different meanings and spellings compared to their original forms. So awful once meant the same as “wonderful.” A bully was originally a friend or a close companion. Jargon was once upon a time another word for the chattering of birds. And while adders and umpires were originally nadders and numpires, nicknames were eke-names

When changes like these happen to entire sayings and expressions, however, the differences between the original form and the form that eventually catches on can be even more surprising … 

1. CLOUD NINE

People who are extremely happy have been “on cloud nine” since the mid-1900s, but according to the Oxford English Dictionary, it wasn’t originally cloud nine that was the seat of all contentment, but “cloud seven.” The phrase itself probably began life as a spin off from the much earlier phrase seventh heaven (which dates back to the 14th century), but records have also been unearthed that mention everywhere from cloud eight to cloud thirty-one. Why is it only cloud nine that’s survived today? No one really knows. 

2. AN APPLE A DAY KEEPS THE DOCTOR AWAY

The old adage that “an apple a day keeps the doctor away” was originally a full-blown proverb: the Oxford English Dictionary has traced “eat an apple on going to bed, and you’ll keep the doctor from earning his bread” back as far as 1866, but it was probably in use locally long before then. By the later 19th century, this had shortened to “an apple a day, no doctor to pay,” before the snappier version we know and use today emerged in the 1910s. 

3. ALWAYS A BRIDESMAID, NEVER A BRIDE

We know the phrase “always a bridesmaid, never a bride” thanks to a 1925 advertisement for Listerine mouthwash. It wasn’t always as pessimistic as it is today, however: The original phrasing was “often a bridesmaid” rather than “always.” There’s hope for everyone, it seems, so long as your breath doesn’t smell.

4. POSSESSION IS NINE-TENTHS OF THE LAW

Possession hasn’t always been proverbially “nine-tenths of the law”—back in the 17th century, the phrase 11 points of the law” was just as common. No one is entirely sure what these “11 points” or “nine-tenths” initially were, but given what the phrase implies it’s presumed that it might once have been necessary to meet a certain number of criteria in order to legally prove your ownership of some disputed property, and it’s these criteria that were the original “11 points” involved. 

5. SHOOT YOUR CUFFS

If you “shoot your cuffs,” then you pull your shirt sleeves down so that they can be seen sticking out of your coat or jacket sleeves, although the phrase can also be used figuratively to mean “to smarten yourself up.” It dates back to the mid-19th century, when the original wording was “shoot your linen”; the more specific mention of “cuffs” emerged in the early 1900s. 

6. DON’T LOSE THE SHIP (FOR A HALFPENNYWORTH OF TAR)

Or, as you might also know it, “don’t spoil the ship for a ha’p’orth of tar.” In either case, back in the 17th century the original phrasing was "lose the sheep" not the "ship," which is presumed to refer to the use of tar either to mark ownership of the sheep in a flock, or to cover up sores on the skin of livestock to stop them from being bothered by flies. But because ship and sheep sound so similar (and because tar can also be used to seal the timbers in leaking ships), the two forms quickly became confused and today the “ship” form has become the standard.  

7. GILD THE LILY

Along with being “in a pickle,” a “foregone conclusion,” and “what the dickens,” we owe the expression to "gild the lily" to William Shakespeare, who coined it in King John in 1595. You won’t find the form we use today in Shakespeare’s original speech, however: 

Therefore, to be possessed with double pomp,
To guard a title that was rich before,

To gild refined gold, to paint the lily,

To throw a perfume on the violet,

To smooth the ice, or add another hue

Unto the rainbow, or with taper-light

To seek the beauteous eye of heaven to garnish,
Is wasteful and ridiculous excess.

King John (Act 4, Scene 2) 

Included in a list of metaphorically unnecessary acts, the original phrase was “paint the lily,” while it was the “refined gold” that was being needlessly gilt (i.e. coated in gold). When this quotation became proverbial in the early 20th century, Shakespeare’s original wording remained intact (the OED has found a reference to “painting the lily” as recently in 1968 in the Encyclopedia Britannica), but soon the conflated form “gild the lily” became the standard and has remained in use every since.