With our hectic schedules, it’s easy to pour all of our energy into content, and to skip little niceties that distinguish our message from the dozens of others that bombard our readers on a daily basis. Type crimes aren’t only in your document, but all over the place, on signage, advertisements, and in restaurant menus. Punctuation is decidedly critical, but is often used with wild abandon, which can be a major distraction from the message. Nothing seems to subtly whisper “amateur” in a reader’s ear more than an apostrophe out of place, and two mistakes that drive me bananas are its misuse in possessive vs. plural, and in a contraction (particularly maddening is a right-facing apostrophe in the two-digit year).

Misuses of the apostrophe

An apostrophe’s main job is to show a possessive, but they’re far too often exploited in a variety of erroneous ways—the most common is to insert it before the s in a plural (e.g. American’s, Wine-down Wednesday’s). The confusion may be a result of the contrary: the apostrophe is considered correctly used in “dot your i’s and cross your t’s”, “she got all A’s on the test” (when following a single letter or number), and “1980’s” (yes, even though this is plural). In a contraction, the apostrophe is curved toward the missing letters (e.g. can’t, where ’ is in place of “no”), and should be treated no differently when used in an abbreviated year or shortened word. The apostrophe—also known as the single closing quote—should curve left, to replace “20” in ’08, or “th” in ’em.
To dive even deeper, curly apostrophes differ from vertically-shaped primes like a fine Pinot differs from a carafe of house red. Without a doubt, I’d serve the Pinot from the cellar—it’s just the more distinguished thing to do. In the same way, the elegant curvature of curly apostrophes, also called “smart” quotes, is something of an ethical decision. Note that certain typefaces are less curly than others—see Apple’s iLife headline, set in Myriad Pro semibold—but left-facing nonetheless. And, as with most english grammar, there are the exceptions: when indicating feet and inches.To set options in MS Word to automatically create curly quotes and apostrophes, from the Tools menu, choose AutoCorrect Options and check the boxes to replace straight quotes with smart quotes.

Smart quotes key commands on a Mac, or in a layout program such as InDesign or Quark:
Single open quote: option-]
Single close quote: shift-option-]
Double open quote: option-[
Double close quote: shift-option-[

Smart quotes key codes using Windows (the character doesn’t appear until alt is released, and you must use the number pad on the right side of your keyboard):
Single open quote: alt-0145
Single close quote: alt-0146
Double open quote: alt-0147
Double close quote: alt-0148

Test your apostrophe savvy—play the Eats, Shoots & Leaves punctuation game!