Oprah. Love or like the gal (who can hate her?), I doubt you’ve spent more time thinking about her than I have. I also doubt that anyone besides someone selling something has spent so much time lobbying her for a favor.

Full disclosure: I am Red Square’s Oprah guy. Even before I worked at Red Square, I was their Oprah guy. I wrote the first 100 tweets for its @YoOprah Twitter project. Don’t know about Yo?

@YoOprah is one of our many internal projects. More than any other, it’s strictly a publicity project. Its purpose is to solicit a #FF from @Oprah for @redsquareagency (her first ever, as far as we know). The thinking goes: If only half a percent of Oprah’s followers followed us, we’d have 45,000 new followers.

So far we have written about 400 tweets at her (270 by me, 130 by Nick Ewertz). They have ranged in style from direct petitioning to word play to prose to sending @YoOprah on soul-searching adventures into the American west. Each tweet is treated as if it were a client-facing headline.

Now we’re adding line extensions. Last week saw the genesis of @DearestOprah, the high tea and croquet-playing, butler-mistreating aristocrat whose May 13th #FF Masquerade Brunch is, at least in her mind, the day on which the much sought #FF will be literally served to us on a silver platter. So how much do I think about Oprah? Here are some other @YoOprah spinoffs anticipating launch in early 2012:

@CiaoOprah (Bringing much needed ragu and ravioli to the #FF quest.)
@HowdyOprah (If Oprah won’t give up a #FF, @HowdyOprah’ll wrangle it herself.)
@NuqnehOprah (“Nuqneh” is Klingon for “hello.” Coming 2364, if we still have #FFs.)
@AvastYeOprah (Pirate Oprah. She’d walk the plank for a #FF.)
@BraaaaainsOprah (“Braaaaains” is how zombies say “Hello, could you spare a #FF?”)
@KupoOprah (Part Moogle, part Oprah. If you thought a Star Trek Oprah was nerdy, think again.)

Why so many Oprahs? There’s a chance she blocked @YoOprah a long time ago. And we still want a #FF. Maybe it’ll secure us a small place in Twitter history. Maybe it’ll help us leverage our brand into a new market. In the meantime, if you need me, I’ll be working on @你好Oprah, but first I need to learn Mandarin.

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“Short and sweet.” It’s a cliché. It’s also a condition which everything from wedding vows to Academy Awards acceptance speeches should strive to be. To a copywriter, headlines are the supreme articulation of shortness + sweetness. That said, the quest for the right headline is almost never short or sweet. It’s long. It’s painful. It’s the copywriter’s crucible.

Some just think of the process as headline writing—the scribbling out of a small batch of lines and picking the winner. Others practice a more formal approach to finding the ideal headline. It’s known as the “100 Headlines.” It goes like this: you need a headline. Ideally, it will be a headline that can raise a brand’s sales by double-digit percentages and define it through future decades using fewer words than you find on a Surgeon General’s Warning. For this, you will need to write 100. Then junk 99 of them.

If you went to ad school then you know the 100 Headlines as the process popularized by Luke Sullivan, but immortalized by Sally Hogshead (She would want me to point out that yes, it is her real name). Hogshead’s “800 Headlines” were for BMW Motorcycles. Her agency needed eight ads. You might say, “Well, it’s easy to sell motorcycles to men.” And it is. But, writing copy that defines a company like BMW when you’re simply a junior copywriter—not so easy. So, why 100? Why not scribble out 10–15, hand ‘em off and jump back on Facebook?

Because your first 15 are usually junk. And so are your first 30, 40 and sometimes 50. Like rock music, greatness doesn’t even become possible until the mid-50s.

Let’s say I am writing headlines for a car insurance company. Chances are they aren’t my insurance provider; I’ve never been to their office; and I am unable to tell their policies from those of their competitors. Odds are good that my first shot at a headline will not make its CEO invite me over for dinner. Indeed, Hogshead wrote those 800 without so much as ever revving a motorcycle—let alone a BMW. Let’s choose an everyman’s car insurance company and go with State Farm. In just over one minute, here are five headlines:

- Life happens fast. State Farm happens faster.

- You’ve been there for others. Now let us be there for you.

- Some auto insurers claim to have your back. We’ve got your front too.

- Take some of the risk out of turning the key.

- It’s funny to think that such a small piece of plastic can cover so much ground.

Bleh. Blah. Yuck. People turn mountains into gravel looking for diamonds scarcely bigger than a pencil eraser. It’s a lot of work for such a little thing. In the process: people die, limbs are lost, and countries tumble into civil war. All of this when we have labs making diamonds so stunning that no one except an expert can tell them from the genuine article. So why not get by with imitations? Why do so much for so little? Because it’s a diamond, and people have gotten divorced for much less. And most headlines suck. Next time, write 100. It won’t be short. It won’t be sweet. But if you survive, your boss and your client will thank you. They might even invite you over for dinner.

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