What It's Like to Photograph Everyone from MLK to Trump

Harry Benson has enough photos of President-Elect Donald J. Trump that he could probably release a book on him. These images, some of which can be found in Matthew Miele and Justin Bare's new documentary, Harry Benson: Shoot First, are the product of a 40-year-working relationship between the legendary photographer and the soon-to-be president.

"I've known the bastard 40 years," the 87-year-old Benson recently told me, sitting in his artsy, light-filled Upper West Side apartment. "He's still the same show-off." Benson would know. In the film, Benson shoots Trump in 1990 holding a stack of a million dollars, pulled from his Atlantic City casinos. And Trump isn't the only important figure in American history to get the Harry Benson treatment; members of the Ku Klux Klan also feature in the photojournalist's work. "I was taken in by the Imperial Wizard, and that helps," Benson said, explaining how he became so deeply embedded in Carolina Klan country that he was able to shoot rallies. "It was a man by the name of Bobby Shelton."

When I bring it up, the Glasgow, Scotland-born photographer tells me he has "no desire" to shoot the president-elect, which will make Trump the first president since Eisenhower that Benson hasn't shot while in office. Similarly, he's also had enough of shooting the Klan. "I don't have to be so ambitious anymore," he said. "I'm an old man."

Though outwardly self-depreciating, Benson was certainly ambitious in his younger days, having shot everyone from the Beatles to Muhammad Ali, Greta Garbo to Mike Tyson; he also embedded with the IRA and for wartime assignments in Bosnia and Iraq. A cover photo he shot of Ronald and Nancy Reagan dancing in a studio for Vanity Fair was even credited with saving the publication from the chopping block.

Benson shot the Beatles' first stateside trip, and he also shot Jack Nicholson on the side of the highway in Aspen with a bit of white powder still in his nose. His camera captured national tragedies, such as the 1968 assassination of Senator Robert F. Kennedy, and quieter moments like the famously reclusive Greta Garbo as she swam in Antigua. All of this is shown and given context in the film by the likes of Trump himself, RFK's daughter, Kerry Kennedy, Dan Rather, Sharon Stone, Piers Morgan, and more.

"I wasn't going to go to the Ambassador Hotel because I knew Bobby had won," Benson said of the post-assassination shots. "I go there, and Bobby makes a speech at the hotel. I try to leave, but it's a crowded ballroom, so I try to figure out which way to go. I'm accredited, so I get behind Bobby, and we're walking out through the kitchen. I turn to go one way and a girl screams—she was a Kennedy—and right away I knew what it was." That wasn't the only time Benson shot in the aftermath of a murder—he also shot Martin Luther King Jr.'s funeral, following his assassination that same year. "I had the ability to leave my emotions behind me," Benson explains in the film.

But for someone so comfortable behind the lens, Benson was hesitant about being the subject of a film: "I don't really think I'm that good at shooting photographs," Benson said. "It was awkward. I had to fight through it because I'm used to photographing people, and I can see sometimes how stupid and awkward I look."

For Bare and Miele, the decision to make Shoot First came in the middle of another project: While working on a film for Tiffany and Company, the pair were put in touch with the photographer. "After about ten minutes, we realized this guy was off the charts in terms of who he is in terms of photography," Miele said. "He was being modest. He didn't mention much, but as you're talking to him in his apartment, there are all these images around you." Indeed: When I visited Benson's apartment, there was a room where every wall was covered with large-size photographs, the subjects ranging from Andy Warhol to two random lovers making out at a bar.

Many of these images make it into Shoot First, and piles more sit in oversize boxes. They're all organized by his wife, Gigi, who's also his business manager. Each time he unearthed a box of new photos during my visit, Gigi—either of her own volition or at Harry's request—would tidy up behind him when he was done.

"We wanted to represent every decade that he was working," Miele told me of the film's final edit, which took about a year to finish. The result is extensive, and wide-ranging: Images of Jacqueline Kennedy flash onscreen, along with a scene about photographing Michael Jackson and how Benson knew, upon entering his bedroom, that the resulting photos—which featured a life-size boy scout statue as well as an enormous gilded throne—would be "weird."

The color and action with which Bare and Miele fill Shoot First are indicative of Benson's work, which will see him earn the 2017 Infinity Award for Lifetime Achievement from the International Center of Photography.

There isn't much that Harry Benson won't shoot, although he did admit to me that he would never take an assignment where animals were being harmed due to humans. For him, as long as he's on the assignment, he will shoot first and leave editing and deciding what to run to someone else.

"People ask me if I have nightmares for taking it," Benson said of those heart-wrenching shots of Kennedy's last moments, his wife, Ethel, holding up her hand to block the camera's view. "But I would have had nightmares if I hadn't have taken it."

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Harry Benson: Shoot First is now in theaters and available online.