The apostrophe: typewriter or typographical?
When and where to place an apostrophe can be confusing , but there’s more to an apostrophe than simply grammar and punctuation. Appearance matters too. Do you ever notice what an apostrophe looks like? Have you perhaps seen that there can be two versions of an apostrophe (and that it’s the same with quotation marks). What does an apostrophe or a quotation mark look like when you write them? And what should they look like in printed text or on a website? Are they elegant, or incongruous?
Going back to their beginnings, the apostrophe and single closing quotation mark shared a classic shape with the comma. It’s a shape that originated in ancient manuscript writing: a point with a downward tail curving clockwise .
In the early days of type design, the book printers of the Italian Renaissance drew inspiration from Roman capitals for their upper-case (ABC) letters and from an obsolete but once widely used European script, the Carolingian Miniscule, for lower-case (abc) letters. Commas, apostrophes and quotation marks, along with other punctuation marks, were incorporated in Renaissance type designs that we still use today. Modern versions of those typefaces remain true to the original designs, even though they have been redrawn to adapt them for modern printing and publishing technology. Down through the centuries the apostrophe, comma and quotation marks retained their shape based on a point with a downward curving tail. This is clear to see in classic typefaces such as Baskerville, Bembo, and Garamond, which are still widely used in print, word-processing, and in websites. The sample text below shows the elegance of the apostrophe, comma and single quotation marks in Bembo Roman, a classic font from Linotype.
From the fifteenth to the twentieth century, apostrophes, commas, and quotation marks retained their classic typographical shape, in harmony with whatever typeface they belonged to; until the arrival of the typewriter.
Just as metal type had brought about a revolution in printing, by the beginning of the twentieth century typewriters were causing a revolution in business practice across the industrialised countries of Europe and North America. Clerical work that had been done for centuries by hand, relying on office workers with pen and ink and neat handwriting, could now be typed on paper and look as uniformly professional as printed text.
This is where you could say the apostrophe and quotation marks drifted away from the comma and began to lead a double life.
Typewriter keyboards were designed for economical production and efficient use. The number of keys on a typewriter was kept to a bare minimum. Each key bar would have two characters, an upper and a lower-case letter for example, or a number with a punctuation mark or a symbol; this efficiency was later carried over to computer keyboards.
The early QWERTY typewriters had no specific key for 1 and 0 because those numbers could be produced using the capital letters I and O respectively. Similarly, a single prime ( ' ) was used not only as the symbol indicating measurement in feet, together with the double prime ( " ) for inches, but also as an apostrophe. Single and double primes were also used for single and double quotation marks, with no difference between opening and closing quotes. On some early typewriters it was necessary to type a single prime, followed by a backspace and then a full stop, to produce an exclamation mark!
As typewriters made way for computers, and letters and symbols were given codes to identify them within electronic systems, the prime infiltrated type designs and, as previously with typewriters, continued to double for quotation marks and apostrophes.
Unicode  does not discriminate between typographical or non-typographical punctuation marks and symbols. It simply codes them all. Once you become aware of the visual difference between a vertical prime, or typewriter apostrophe (U+0027 in Unicode) and a typographical apostrophe (U+2019) you’ll be able to make an informed choice, and a choice is usually available. From a typographical point of view, primes are incorrectly used as apostrophes and quotation marks; they need to be replaced with the typographical version. Even apostrophes in sans serif fonts, that no longer have the classic shape of a point with a downward curl, have a typographical form. That form might have more of a slanting, slightly wedge-like shape, but it will be clearly distinguishable from a prime.
While primes or straight quotes (also known as dumb quotes) often appear on your computer screen as the default, word-processing programs provide an option. In Microsoft Word, for example, use Preferences: Auto Correct to automatically replace "Straight quotes" with “Smart quotes”; this option also replaces a straight apostrophe ( ' ) with the typographical version ( ’ ).
Where primes are the default for website text, the content management system should offer a palette where you can choose the typographical option for apostrophes and quotation marks. Or you might simply need to backspace for the typographical option to magically appear, as I discovered when I was building my website in Squarespace.
With more awareness of typographical conventions, the norm might shift in favour of typographical apostrophes and quotation marks and away from primes. It’s a professional and an aesthetic choice, and the choice is yours: typewriter or typographical?
 Simple rules for use of an apostrophe: a) Possession – the dog’s collar or the dogs’ bones (the collar belonging to one dog or the bones belonging to more than one dog), BUT with its bone (the bone belonging to it) the word its has no apostrophe. b) Omission – in contractions, where one or more letters or numbers have been left out, such as t’other instead of the other, it’s for it is or it has and ’18 for 2018. Opinions differ on certain usage: Would you say dos and don’ts or do’s and don’ts? An apostrophe in do’s is an exception to the rule for plurals but, as with dotting the i’s, it makes the meaning clearer.
 Rotate this shape on its point, 180 degrees, and you have a single opening quotation mark.
 Unicode is ‘an international encoding standard for use with different languages and scripts, by which each letter, digit, or symbol is assigned a unique numeric value that applies across different platforms and programs’ (Oxford Dictionary, 2019).
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