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The day I worked with Donald Trump.

Back in the Noughties, in the halcyon days of big brand advertising, I was a creative director at J. Walter Thompson New York, possibly the world’s oldest and biggest ad agency. JWT was going through a creative renaissance of sorts and had just won the Macy’s department store business with a bold idea that we pitched – using the celebrity star power of the famous name brands Macy’s sells to create some noise. Basically, shooting celebrities as ‘themselves’, working at Macy’s. Like they would. The campaign was titled “The Magic of Macy’s”.

Of course, this was a giant, expensive, logistical nightmare. Not only could we not shoot in The World’s Largest Department Store on 34th Street, but many of our potential cast members had tabloid-sized gripes with each other that prevented them from being in the same room together. No problem. Nothing we can’t solve by adding a few zeroes and fixing it in post.

We set about building a 1:1 scale replica of a multi-level Macy’s store in a studio in Brooklyn Navy Yard and writing scripts that brought the idea to life. Scores of them. Mariah Carey working behind the fragrance counter, approved. P. Diddy in an act of congregation with customers, approved. Martha Stewart’s scolding her daughter in the kitchenware department, Carlos Santana playing guitar in the shoes department and Jessica Simpson serving the blonde cliché, also approved. Ralph Lauren working in the jeans department and serving Clint Eastwood, rejected. Before we knew it, we had signed up quite the cast of famous people to be a part of the action. Including the purveyor of some eponymously named, Chinese-made, men’s neckties and belts; Donald J. Trump.

It’s handy to remind ourselves that at this point in mankind’s struggle – 2007 – The Donald was still pretty much a New York tabloid punching bag, circling the drain of reality television and threatening to rebuild the World Trade Center. Students of advertising would know that by this point, Trump had already played himself in some questionable commercials for both Pizza Hut and Domino’s Pizza over the years, amongst others.

Donald appeared as a cameo in three or four of our scripts, and soon we were doing some conference calls with the people at the Trump Organisation to walk them through the proposed scenes. All good, but some nerves were fraying about the scene where the camera finds Donald in front of a store mirror, using a hairdryer to coiffure the infamous Trump mane.

Donald Trump was quite complimentary of his portrait that we had painted for the scene.

Fortunately, we had enlisted Oscar-winning Hollywood director Barry Levinson to steer us to a good place on this project, as he’d seen it all before with these celebrity types.

Which was all very handy for when the Donald showed up in an ageing limo (which I am positive had a fax machine) and swiftly walked on set to direct himself. The Donald marched around and called ‘action’ and ‘cut’ and shouted ‘that was a great take, Barry’, which we duly noted.

We pulled Donald aside to brief him on the hairdryer scene, talked him through his ‘motivation’, and floated the idea out there. The production department had prepped two hair dryers for the scene, one that blew regular hot air (apt, I know), and one that only made sound, in case Donald did not want to actually %$#@ with his carefully assembled hair. To his credit, he shouted that ‘of course I’ll use the real one, then everyone will know this hair is real’, and something about Rosie O’Donnell.

We shot the whole thing in minutes. He waved and shouted as he left the set for the limo back to Manhattan, no doubt faxing people along the way.

That's real hot air, there.

"That's great."

The Macy’s commercials (a few of them are below) never changed the world. But they were fun to write and fun to make. Apparently, they moved the needle for Macy’s and they continued to make them for years after I had moved off the account. Looking back, they also seem to serve as a strange time capsule to a not-to-distant time, when this B-list real estate guy was happy to play a parody version of himself, and the idea that he’d ever step into the realm of geo-politics, trade wars, non-proliferation treaties, walls and all the rest seemed like just a crazy fantasy. The part that I still wonder about is, who faxes?


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