Is it possible to change the email "To" field from what's in Address Book?

I would like to change the name displayed in the "to" address from the way it's entered in the address book but can't find how to do this. I like to have the address book sort alphabetically by last name (so it's set up with last name first), but I don't always want to send an email in that format. For example, I'd like to change "Smith Family" (address book) or "Smith John" (address book) to "John Smith" when I'm sending an email, or even just the email address (without a display). I could do this in Outlook, but I can't find the same feature in Mac Mail. Even when I delete the display name and try to retype just the email address it just "bounces back" to whatever the name is in the address book. I hate to have to make multiple entries in the address book for the same family/email address just to get different display names. Is there a way around this??

I'm sorry, but I'm still not clear on the problem. Do you mean that you have both "Smith Family" and "John Smith" tied to the same email address? If so, again, that "friendly" name isn't sent to the recipient, so the person receiving the email will get exactly the same thing regardless of whether you select the "Smith Family" entry or the "John Smith" entry. The "friendly" name doesn't go along as part of the email.
It would only matter on your end when looking at your Sent email, and if that's an issue, it should be no problem to select which one you want; just start entering in the email address/name and wait a second; you'll get a dropdown with all the addresses that meet that criteria and you can just pick the correct one.
Forgive me if I'm still not understanding what the difficult is or what you're trying to accomplish.

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