Type “the ’90s” in most word processors and you’ll often get ‘90s instead, with the apostrophe curling the wrong way. Designers spot it immediately. It’s one of the most common typographic mistakes in the world, and it happens because of how the apostrophe was built in the first place.

A Short History of the Apostrophe

The word comes from the Greek apostrophos, meaning “turning away.” It first described a mark showing that a letter had been dropped from a word, called an elision. English borrowed the mark from French printers in the 16th century, and at first it did only that job: marking missing letters, as in “don’t” for “do not” or “o’er” for “over.”

The possessive use came later. In Old English, possessives were formed with an “-es” ending, so “the king’s house” was once written as “the kinges house.” As that “e” dropped out of speech, writers marked its absence with an apostrophe, and the mark became a signal for possession. By the 18th century it had been fixed in that role, though the rules weren’t fully standardized until the 19th century.

The mark has been arguing with itself ever since. English still can’t settle on whether it’s “its” or “it’s,” and signs reading “Banana’s 50p” have a nickname: the greengrocer’s apostrophe. In 2009 Birmingham City Council in the United Kingdom announced that it would stop using apostrophes in street names, citing confusion, and the decision set off a minor national argument.

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Anatomy of an Apostrophe

An apostrophe is, structurally, a comma lifted to the top of the line. It has a head, the rounded or wedge-shaped top, and a tail that curves downward and to the left. Its shape is identical to the closing single quotation mark, the mark that looks like a tiny 9, and it usually shares the same character code in digital fonts.

The key design question is its position. The apostrophe hangs from the top of the line, aligned with the cap height or ascender height, so it looks like it’s attached to the letter before it, not floating above the line.

There are two versions in most typefaces. The curly apostrophe has the teardrop-and-tail shape and is the mark typographers prefer. The straight apostrophe is a vertical wedge or rectangle, the typewriter version, and it’s what you get from the key on your keyboard.

Weight and size matter, too. The apostrophe needs to be visible at small sizes, but not so heavy that it draws attention. Its head is typically similar in size to the comma’s head, so the two marks look related.

Designing the Apostrophe From Scratch

Designers draw the apostrophe from the comma. The comma is copied, raised to the cap height, and then adjusted, since a comma’s weight is tuned for the baseline and may look unbalanced at the top of the line.

The most important job is making sure the apostrophe sits comfortably in common combinations: contractions like “don’t” and “it’s,” possessives like “dog’s,” and abbreviated years like “’90s.” In each case it has to be spaced carefully. In “don’t,” for example, it sits tight between the “n” and the “t,” and kerning is needed to keep it from looking detached.

The apostrophe also needs to be differentiated from the opening single quote. In most fonts the two are mirror shapes, but the apostrophe should look like the closing quote, not the opening one. This is where software mistakes come from.

Unique Facts About the Apostrophe

The backward apostrophe in ’90s is a software bug in disguise. Many word processors decide between an opening and closing quote based on what comes before the mark. If there’s a space before it, they assume it’s an opening quote and use the 6-shaped mark. But an apostrophe at the start of a word, as in ’90s, ’em, or rock ’n’ roll, needs the closing 9-shaped version. The software gets it wrong, and the result is ‘90s with a backwards apostrophe.

In some languages, the apostrophe isn’t punctuation at all. In Hawaiian, the ʻokina is a full consonant letter that represents a glottal stop, and it looks like an opening single quote. Ukrainian uses an apostrophe within words to separate sounds. And in programming, straight apostrophes are often used to mark strings of text.

The straight apostrophe is also used as the foot mark, as in 5’10”, which is the same typewriter shortcut covered in the entry on quotation marks. True foot and inch marks are slanted prime marks, but almost nobody types them.

The Apostrophe in Popular Fonts

In Garamond and other old-style serifs, the apostrophe is a teardrop with a gracefully curved tail, echoing a broad-nib pen stroke. Helvetica uses a compact wedge shape with a short tail, matching its neutral character. Futura uses a small, nearly geometric mark with a very short tail.

In script and handwriting fonts, the apostrophe is usually a quick, slightly tilted flick, drawn to look like a pen stroke.

Summary

The apostrophe started as a mark for missing letters, became the signal for possession, and remains one of the most commonly misused marks in English. It’s built from a comma, shares a shape with the closing quote, and gets flipped the wrong way by software when it sits at the start of a word. Spotting the backward apostrophe is one of the quickest ways to tell if someone cared about the typography.

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