The apos­tro­phe has two func­tions we all remem­ber from sixth-grade Eng­lish class.

1. An apos­tro­phe indi­cates the pos­ses­sive case (Jessica’s bagel).
2. In con­trac­tions, an apos­tro­phe takes the place of let­ters or num­bers that have been removed (is not becomes isn’t, Patent No. 5,269,211 becomes ’211).

Apos­tro­phes always point down­ward. If the smart-quote fea­ture of your word proces­sor is on, then type an apos­tro­phe with the same key you use to type a straight sin­gle quote ( ' ). Your word proces­sor will con­vert this char­ac­ter to a curly apos­tro­phe ( ’ ). Or you can type an apos­tro­phe directly, using the same key as a clos­ing sin­gle quote.

Wrin­kles arise when an apos­tro­phe is used at the begin­ning of a word (again, assum­ing your smart-quote fea­ture is on). If you type the phrase:

In the '60s, rock 'n' roll

This will be dis­played as:

In the ‘60s, rock ‘n’ rollwrong

The prob­lem here is that the char­ac­ters in front of 60s and n’ aren’t apos­tro­phes — they’re open­ing sin­gle quotes. They point upward. What you need is an apos­tro­phe in place of each sequence of omit­ted let­ters, so the result looks like this:

In the ’60s, rock ’n’ rollright

To get this result, you have two choices. You can man­u­ally delete the incor­rect marks and type apos­tro­phes directly. Or you can type straight sin­gle quotes twice:

In the ''60s, rock ''n' roll

These will be dis­played as:

In the ‘’60s, rock ‘’n’ roll

Then you can delete the unneeded open­ing sin­gle quotes, get­ting you back to:

In the ’60s, rock ’n’ rollright