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Confessions of a Copywriter #1: The worst headline I’ve ever written

Jonathan Wilcock, Freelance Copywriter – "I am not proud of what I've done"

It was at my first job out of Art College.

The agency: Butler Dennis and Garland (at the time, a top 20 ad agency, in Covent Garden)

The client: Sloggi (women’s briefs)

The core proposition: Sloggi briefs stay brighter and tighter than the competition (no idea how we would have backed that up, but anyway…)

The tactic: Don’t look like anyone else’s knicker ads (fair enough)

I must have been in the job for about a year, still working as a hybrid Copywriter and Art Director at the time. I had this idea, rather than showing smiling models in their knickers, we’d show the competition, all hanging out to dry – looking sad and baggy around the seams.

So, having scamped up the idea and got it past my Group Head, Creative Director, the Account Director and finally the client (I mean, four filters, you’d have thought someone would’ve said, “err… Jonathan, this headline is sickeningly, nauseatingly bad”), we got busy.

First, the Art Buyer (yes, it was that long ago) got a few books in and we secured the services of a superb young photographer, Hugh Johnson, son of esteemed wine buff, Hugh Johnson – must’ve been less names to go around in those days.

No idea what Hugh Junior thought of the idea, but work’s work, and he had a studio to feed in Belgravia. (I’ve just connected with Hugh on LinkedIn and happy to say, this shoot didn’t kill his career – he’s since worked globally for the likes of Lego, Levi’s, Volvo, Audi, Condé Nast, Guinness, David Beckham and M&S)

So bad, should I even be confessing this?

Looking back, everything about this ad was wrong.

Sloggi were (and still are) a big brand. There was a sizeable budget, with single page ads running in all the women’s press. Full colour. Full page. Loads of titles. Must have cost a fortune.

So, there I was, happy as a moth in a lingerie department, playing Copywriter and Art Director. Not only that, I took it upon myself to run around town buying plus-sized knickers and then hand-dyed them a grotty grey in a bucket, in my office.

Hugh shot the seven pairs of sad-looking knickers hanging on a washing line, along with a pristine, bright white pair of Sloggis, against a painted sky backdrop.

And (in my opinion at the time), it looked great.

It was bold. It was different. It stood out a mile against all those other ads with their size 8 models, tropical beaches and perfect teeth.

And that headline? What a headline! Witty, pithy, it got the idea across in a split second, shear blimmin’ brilliance. I was chuffed from pie hole to turn ups.

But with the distance of a few decades, let’s just say I’m not quite so sure now.

OK, I’ve been building up to the big reveal. 3, 2, 1, time to hang my head in shame…

Snow White and the Seven Drawers – the worst headline I've ever written, Jonathan Wilcock

‘Snow White and the Seven Drawers’. Oh, Jonathan, what were you thinking?

And as if that wasn’t bad enough, I’d had the grey knickers screen-printed with ‘SAGGY’, ‘BAGGY’, ‘GROTTY’ etc.

*I wish I had a copy of it. Every time my ego flares up, I could use it to hammer it into submission.

Good old hindsight, but how off could a headline possibly be? Not that I don’t love a good pun, but this was an awful one, an absolute tone of voice nightmare. And I wonder how many pairs of undies they sold off the back of it? Seven would have been a miracle.

I’m so, so, sorry

20-year old me would like to formally apologise to the client, the publications the ad appeared in and my future self. Actually, no he wouldn’t, he thought it was a corker of an ad.

But maybe me realising how awful that headline was is a sign of progress (?)

And surely I’m not the only one with old headlines stinking up the recesses of their creative memory banks.

So, come on, what’s the worst headline you’ve ever written, or been responsible for letting out into the real world? I won’t judge. Honest.

Love and patience

Jonathan xx

Jonathan Wilcock (that’s me) is a Senior Freelance Copywriter.
You can drop me a line here, or email

*If you’re a hoarder, you’ll probably find it in a mag that looks like this. Send me a tear sheet and I’ll buy you at least one pair of undercrackers:

Cosmopolitan cover June 1985