It’s an unprecedented match-up of familiar faces. The major-party presidential candidates, Hillary Clinton and Donald Trump, have spent decades in the public eye as key figures of American culture. Their portraits have covered magazines, newspapers and websites.
We asked some of the greatest portrait shooters who have photographed Donald Trump to scour their archives and select their favorite photographs from these one-on-one sessions.
Here are the stories, told by the photographers, behind these iconic portraits.—Tara Johnson, Chelsea Matiash and Paul Moakley.
William Coupon, portrait photographer, who shot Trump in New York City for Manhattan,inc. in 1983: “I shot Donald Trump twice. This is my favorite. Trump was offering his services as a ‘peace negotiator’ between the Israelis and the Palestinians. We thought: get the bird, which proceeded to leave droppings behind. Trump was amenable enough, but not at all happy. But ultimately, it was that something in his eyes. His eyes. Not the bird’s.”
Michael O’Neill, portrait photographer, who shot Trump in New York City for the New York Times Magazine in 1984: “1984 – in many ways. Gilt, gold, pride… He loved the cover! It was his first for the New York Times Magazine.”
Harry Benson, photojournalist, who shot Trump in Atlantic City, N.J. for People in 1990: “Shortly after the Taj Mahal opened in Atlantic City in 1990, I was there to photograph Donald Trump. He told me there was over a million dollars in the ‘cage’ in the casino where the money is kept. I told him I had never seen a million dollars. Donald proceeded to walk right in and pick up exactly a million dollars to hold for the photograph which caused quite a stir as it was totally against the rules of the casino. When some of the money started to fall off his lap, I found it was the most interesting photograph of the day.”
Max Vadukul, portrait photographer, who shot Trump at Mar-a Largo, Fla., for The New Yorker on May 19, 1997: “This is one of many ‘air’ shots I did with Mr. Trump. There is a lot going in this image, it’s complicated, sophisticated and strong in its power. I had shown Mr. Trump exactly what I wanted and he had that look that says, ‘Oh I can do better than that.’ And after just one effort – because it’s a big effort physically to do this for 12 frames – he totally nailed it and went even further. What I like about this image, which is now an iconic shot, is the attitude, the elegance, the confidence. Of course, I did not know him at all at that time, but the personality came thru and today he is running for President. This image says a lot.”
Tomo Muscionico, photographer, who shot Trump in New York City for Spiegel in September 1999: “Looking back, I think it’s a powerful portrait of a mogul whose body language shows his privilege, sexuality and arrogance. This subtle moment with him in a limousine says it all.”
Platon, photographer, who shot Trump in New York for Fortune on August 21, 2003: “I photographed Mr. Trump at Trump Tower in Manhattan. It was a cathedral of gaudy, post-modern excess. I asked him to look straight into the camera, trying to get his head as symmetrical as possible. With a glint in his eye, he looked at me and said, ‘No – this is my best side.’ He turned to his right cheek, as if to present me with Trump Inc. on his terms. I thought about this moment many times since the picture, and for me, it says something fascinating about the character of this extraordinary, disrupting figure. For me, he understands the media. He’s comfortable within his own skin. He’s happy to play with the process of photography and film, and consequently is able to project his own brand of authenticity. I believe he has singlehandedly transformed the political and media landscape this year. Our presidential election has essentially been turned into a reality TV show. All media pundits and political opponents have been forced to play on Donald’s terms.”
Andres Serrano, photographer, who shot Trump in 2004 for the series America: “Shortly after Sept. 11, I started a series called America. I felt America had been attacked as the ‘enemy’ and I wanted to show who the ‘enemy’ was. I took over a hundred portraits of people from all walks of life over a three-year period. Donald Trump’s portrait, taken in 2004, was the last one taken.”
Chris Buck, photographer, who shot Trump in New York City for Philadelphia Magazine on March 29, 2006: “Once we finished with the required set-ups that my client needed I brought out an 11×14” print from a previous shoot that Donald Trump and I had done together. He asked, ‘What is this?’ I said, ‘I’m giving you this print as a gift—to buy an extra set-up from you.’ He shrugged and said, ‘Okay,’ and this is how I got him to pose for this picture. It’s shot in the conference room for Trump’s real estate business. With Trump now running for president I get a lot of comments on this photograph. Most people see ‘the many faces of Donald Trump,’ but I see it more as ‘the broken man,’ which may well be more a reflection of my state of mind, not his, as is the case for most of my portraits – they’re about my discomfort, not the sitter’s.”
Marco Grob, portrait photographer, who shot Trump in New York City for TIME on April 5, 2011: “I’m interested in faces beyond their genetics. I’ve spent a lifetime wondering why we wear the faces we have. Why do people desire power? What are their motives? Can you see these motives in their faces? Or in their gestures? What about their body language? I’ve met many people of power, and I don’t attempt to provide the answer, but I strive to provide the question. I often wonder who else asks these questions? This frame really spoke to me as one where Trump was trying to connect with me behind the camera. That being said, his connection was ice cold, he was all business.”
Peter Yang, photographer, who shot Trump in New York for Rolling Stone in 2011: “When I was commissioned to photograph Donald Trump in 2011, the first thing that came to mind was this gold-plated tree stump I’d been eyeing at a ritzy furniture store down the street from me. I had been to Trump’s house before (to photograph Melania Trump) and noted the bevy of things gold. Gold leafing on all the walls, a gold front door, even a golden toilet. With the log in mind, the idea of Trump being the Thinker came next, and while I loved the idea, I was pretty sure he would nix it.
On the day of the shoot, I was told to work fast, real fast. His people said I had 10 minutes, which usually meant 5-7 before you’re getting that thanks-and-goodbye handshake. Arnold Schwarzenegger once gave me one of those handshakes after 40 seconds or so. “That’s what I like about you”, he said, “you’re quick.”
I had three setups ready to go when Mr. Trump got there. There were two safe shots, then the Thinker. The first shot was Trump in front of the Manhattan skyline. Pretty standard stuff and it only took a minute. Trump was way more understated than I imagined he’d be, almost soft spoken. I’d mostly seen him firing people on The Apprentice, and I was glad I didn’t get that guy. The second shot was a close-up portrait of him. It’s always interesting to see famous folks up close, and when he, unprompted, pointed and yelled into the camera, I knew I got the shot.
We then walked over to the gold log. I took a deep breath and showed him a picture of the Thinker. Before I could say anything, he grabbed the paper out of my hand, studied it for a moment, and hit his mark on the log. I snapped a few frames, he shook my hand, and was quickly out the door.”
Martin Schoeller, photographer, who shot Trump in New York City for TIME in August 2015: “I wanted to play on this idea that he thinks of himself as a great leader and savior of the American people. I thought what could be better than our national bird. It’s the perfect symbol. Having worked with birds of prey in the past, I knew that it wouldn’t be easy and there would be a lot of room for surprise. I thought those two attitudes colliding was the perfect match.”
Nigel Parry, portrait photographer, who shot Trump in New York for Esquire in November 2015: “After being unable to fulfill the brief due to Mr. Trump insisting that I couldn’t photograph his profile, I decided the only route was a confrontational photograph for a confrontational subject. I think this photo fits the bill.”
Read the Stories Behind the Best Portraits of Hillary Clinton