Dumb Smart Quotes

I was swiping through Instagram and came across an egregious example of bad typesetting on a t-shirt ad. Even worse, it featured America’s most beloved fictional character of all time! Of course I’m referring to Baby Yoda and a t-shirt promoting his candidacy for president. (if you don’t see the mistake, take a closer look at the “apostrophe”.)

A few days later, I was driving through the ’hood and noticed a similar mistake, confidently emblazoned across the rear window of a pickup truck in giant in-your-face letters. The offending copy: ’MERICA. But more like this…

As a graphic designer of good standing in the community, I’m keenly aware that the use of “curly quotes” instead of “straight quotes” is a fundamental typesetting principle—probably at the top of the commandments list, before “Thou shalt not kill thine 90-days-past-due client.”

But the issue with these graphics is a little more complex, getting into the punctuation realm.

The proper way to typeset this truncated word is with a closing single quote, AKA an apostrophe

…in the same way a year abbreviation uses (or should use) a closing single quote/apostrophe, like this:

A leading apostrophe says, “hey you can guess what’s missing so I left it off to be pithy.”

It’s easy to blame poor education – I mean how many people know the difference between your and you’re, there and they’re, yours and yourin’?

But the biggest contributing factor is that our typewriter heritage was adapted by our computer keyboards and software and survives to this day. This legacy led to our publishing software’s concept of smart quotes/curly quotes and dumb quotes/straight quotes.

Modern software, be it by Microsoft, Google, or Adobe assumes (rightly) that most users don’t know how to type proper quote characters even if they know what proper is. The dumb keyboard makes typing a real curly quote a feat of finger gymnastics and memorization. So, when we try to put something in quotations using the legacy keyboard’s single prime/double prime keys, the software tries to correct punctuation for us, replacing stupid keyboard straight quotes (which are typographically incorrect but typewriterly correct) with curly quotes aka smart quotes!

Way to GO computer! But when we need a single apostrophe or closed leading single-quote, the dumb ’pooter thinks we want an open single-quote. AI may be able to pahk a cah but it’s not so smaht when it comes to punctuation.


My recommendation is A) know where to use quotes and apostrophes, B) know how to TYPE quotes and apostrophes, and C) finger yoga up before bustin’ these keyboard moves.

How to selectively type open and closes single and double quotes.

PC Keyboard with a keypad: (hold alt and type numbers sequentially and make sure num-lock is engaged)

Open/left single quote ‘= alt 0145

Closed/right single quote/apostrophe  ’= alt 0146

Open/left double quote “= alt 0147

Closed/right double quote ”= alt 0148

Mac (hold keys simultaneously)

Open/left single quote ‘= option ]

Closed/right single quote/apostrophe  ’ = shift option  ]

Open/left double quote “= option [

Closed/right double quote  ”= shift option [

Laptop keyboard

If your keyboard lacks a numeric keypad, as do most laptops, you’re supposed to use the Character Map instead. (Kill me…) Anyway, to launch it, press the Start key + R and type “charmap” in the Run box. When it opens, find the character you want to insert and press Select. Copy when all the characters you want to add are selected.

Instead (I think this is easier), I take advantage of software’s smart quotes. For an apostrophe, type a word within an open and closed single quote, which autocorrects to curly, then copy the closed single quote and paste it where you need the apostrophe.

iOS: If you use this trick you may actually be more particular/peculiar then me. Press and hold the single or double quote buttons and you’ll see all sorts of character options.

BONUS TIP: This is the also the technique for typing a degree symbol—press and hold the 0 (zero) character and boom.


With these keyboarding tools and a keen knowledge of apostrophe use, you can confidently create graphics that say, I’m a ’MERICAN!

I’m still waiting to hear back from the baby Yoda t-shirt guy after posting friendly advice on his ad.


Stay tuned for some hot design opinions about prime characters.