Morning!

This week I was on a podcast where I got asked a random question out of left field….

“What’s your favourite ad of all time?”

As a man who has spent the last 5 years writing a weekly newsletter about history’s greatest marketing, I should’ve had a quick answer. But the truth is, I was a little stumped. There are 100s of ads over the years that I've written essays about and loved, but which do I truly think is the best?

Well, I decided to use this essay to decide that.

So, here’s (in my opinion) the 3 greatest ads of all time 👇🏻

The oldest ad ever recorded was created around 3000 BC.

It was a piece of papyrus, written by an Egyptian fabric merchant called Hapu, offering a reward for a runaway slave called Shem. Hapu didn't just want to catch his slave. He also used the papyrus to plug his weaving shop, describing the fabrics he sold and where to find him. Two commercial goals in one ad, 5,000 years before anyone had even heard of a Google campaign.

That papyrus is still on display at the British Museum today.

In the 5,000 years since, we've come a hell of a long way.

Papyrus turned into painted shop signs. Painted shop signs turned into printed pamphlets after Gutenberg invented the printing press around 1440. Printed pamphlets turned into newspaper ads in the 1600s. Newspaper ads turned into radio spots in the 1920s. Radio turned into television in the 1940s. Television turned into digital banners in the 1990s, then social media ads in the 2000s, and now, in 2025, we've somehow ended up in a world where TikTok is flooded with AI-generated videos of talking vegetables trying to sell you protein powder.

Somewhere along the way, humanity produced a lot of advertising.

Nobody knows the exact number. But when you factor in every printed poster, every radio jingle, every TV spot, every YouTube pre-roll, every Instagram carousel and every AI-slop TikTok video ever created, we're comfortably in the trillions.

Trillions of ads. Made over five millennia. All fighting for the same thing. Your attention.

So, which one is the greatest?

Well, for me… it’s these 3 👇🏻

In 1962, Avis walked into a small Manhattan advertising agency called Doyle Dane Bernbach with a very simple problem.

They were losing.

Hertz was the undisputed king of the American rental car market. They had more cars, more locations, and a marketing budget that made Avis's look like a rounding error. Avis, meanwhile, had lost money for thirteen years in a row. In their most recent year alone, they'd bled $3.2 million and were sitting on a modest 11% market share.

Any other agency in New York would have done the obvious thing. They would have written ads telling the world how great Avis's cars were. How friendly their staff was. How affordable their prices were. The classic "we're just as good as the leader" playbook.

Doyle Dane Bernbach did the opposite.

They looked at Avis and told them to admit they were number two.

The ad itself was almost embarrassingly honest. It went on to explain that because Avis wasn't the market leader, they couldn't afford dirty ashtrays, half-empty petrol tanks, or grumpy staff. They had to try harder just to stay in the game.

Two years later, Avis was making a $1.2 million profit. Their market share had exploded from 11% to 35%. Hertz was still number one, but the gap had narrowed to almost nothing. The campaign kept running for the next 50 years.

The reason this ad is one of the greatest ever written is that it discovered one of the most underused shortcuts in all of marketing.

Self-admission.

The moment you honestly admit a weakness, customers believe every other claim you make. Because you've just proved that you're willing to tell the truth even when it costs you. Every marketer wants their audience to trust them. Very few are willing to earn that trust the way Avis did.

Over the last six months, I've slowly picked up a small fascination with watches.

There are hundreds of brands out there. Thousands of designs. Every price point and shape and material you could imagine. And yet, no matter how many watches I look at, I keep finding myself pulled back to Rolex and the feeling of what wearing one represents.

Three weeks ago, I spent an entire week researching Rolex to write an essay (SEE IT HERE) on their marketing. And when I dug into their history, I found the ad that I think is at least partly responsible for how I, and probably millions of others, actually feel about the brand.

In 1956, Rolex ran a campaign in American magazines with a single, audacious line.

"Men who guide the destinies of the world wear Rolex watches."

Just before the campaign, Rolex had personally gifted watches to men like Eisenhower and Churchill on the promise that the brand wouldn't use their identities commercially. They didn’t, but they used the fact that they were the watches to completely shift their brand image.

The campaign ran for a decade. And the aspirational positioning it created has quietly powered Rolex's marketing for the last 70 years. Every time you see a Rolex on the wrist of a Formula 1 driver, a Wimbledon champion, or a president signing an executive order, that ad is quietly reinforcing itself.

The reason this is one of the greatest ads ever written for me is because it created one of the most powerful and well-known brands on the planet. It created a feeling that still exists today 70+ years on.

David Abbott was, in my opinion, the greatest British copywriter of the last 50 years.

He co-founded Abbott Mead Vickers BBDO in 1977 and spent the next thirty years writing some of the most iconic British ads ever made. Volvo. The Economist. Yellow Pages. The RSPCA. If you grew up in Britain and remember an ad from your childhood, there's a decent chance David Abbott had a hand in it.

But out of all the incredible work he produced, the ad that stuck with me most was a small piece of copy he wrote for Sainsbury's in the 1980s.

No jingle. No slogan. No creative wordplay. Just twelve words of dry, unmissable fact.

But what a fact.

Every other supermarket in Britain in the 1980s was selling mince that had been on the shelves for two, three, sometimes seven days. Sainsbury's was quietly telling you, without a hint of showing off, that theirs was fresher than anyone else's.

The reason this ad is one of the greatest ever written comes down to a lesson I first learned from Harry Dry, who's probably the best modern-day copywriter around. Harry has a simple mental model for writing great headlines. He says: say the most interesting fact.

Find the single most differentiating truth about your product, and just say it. Plainly. In as few words as possible.

Most marketers get this wrong because they don't know what their most interesting fact actually is. Or worse, they know exactly what it is, but they think it's too boring to lead with. Every time, without fail, the most interesting fact is more interesting than the clever line the marketer was about to write instead.

This essay took me forever to write because there truly are some amazing ads that went out over the years. But the core principles of these 3 are something I think about every week when working on campaigns.

I’m curious which ads you think I should’ve included here? Reply to this email and let me know.

Until next Sunday,

— Niall

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