Inside Playful Photo Shoots

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Outside a cabin in Los Angeles last spring, Amy Kellner, a senior photo editor for The New York Times Magazine, faced a conundrum. The prop stylist had ordered more than 100 wildflowers as well as proteas, tulips and artificial flowers so that the comedian Seth Rogen, the subject of a cover shoot, could lie down in them. But when the photographer, Chris Buck, took test shots from above, he realized that Mr. Rogen’s facial features would appear distorted from that angle. So Mr. Buck came up with a quick solution: String the blooms on chicken wire, held up by clamp stands — and ask a standing Rogen to stick his head through. “He was game,” Ms. Kellner said.

The shoot with Mr. Rogen is just one of the dozens of ambitious, stylistically inventive photo shoots that regularly appear in the magazine each year, seemingly effortlessly. But behind the scenes, weeks of preparation go into shoots, which may take as long as four hours, involve more than a dozen people and result in hundreds of outtakes. Here’s a look at how they come together.

Brainstorming the concept

Preparation for a photo shoot can take anywhere between a week and three months. The first step is a brainstorming meeting with the magazine’s creative team, led by Jake Silverstein, the editor in chief, Gail Bichler, the creative director, and Kathy Ryan, the director of photography. For the session about Mr. Rogen, Ms. Kellner and Mr. Buck brainstormed for a week before proposing about a dozen concepts. Their ideas included photographing Mr. Rogen in a teddy bear costume, with his head in a jar and even with a flock of woodland creatures, possibly with a skunk on his shoulder as a nod to marijuana (Mr. Rogen is the co-founder of a cannabis company).

Once everyone has agreed on a concept, the creative team then works with the photographer to refine the idea — which may evolve until the day of the shoot.

A celebrity might know the concept of a shoot before stepping on set — but sometimes, the idea is a surprise, or the plan changes. “You want to capture their personality, but you sometimes don’t know what that is until you meet them,” said David Carthas, a photo editor for the magazine. “That’s the challenge.”

Preparing for the photo shoot

Before a shoot, photo editors try to learn as much about their subjects as possible, including how a subject has previously been photographed, to ensure that the concept is fresh.

“People have no idea the research it takes to create original photography,” Ms. Kellner said.

The creative team does whatever it takes to bring a concept to life. Each photo shoot presents it’s own challenges, and the team must adapt quickly. For example, Ms. Kellner said that, for a cover shoot with the “Better Call Saul” actor Bob Odenkirk, the photographer, Zachary Scott, drove a barrel cactus 14 hours from his backyard in California to the shoot’s location in Albuquerque. Mr. Odenkirk ended up talking to, dancing with and — eventually — sitting on the cactus for a photo. (There was a small, clear piece of plexiglass between him and the cactus.)

Even the images that stem from spur-of-the-moment ideas on set only happen because the creative team has done the research and developed an aesthetic before the shoot, Ms. Ryan said. “You create your own luck,” she said.

Taking risky photographs

Though the team will always take some conventional portraits, it’s the risky photos that usually land in the magazine. “We have to take chances. We go in prepared and then the magic happens; then you’re ready to embrace the spontaneous,” Ms. Ryan said.

For example, the creative team and the photographer Arielle Bobb-Willis had a vision for a monochromatic shoot for Billie Eilish’s cover of the March 2020 issue. Ms. Eilish was dressed in all green (including her green hair) and was photographed in front of a green background. She was ultimately captured in an unusual pose: bending backward.

“Arielle is amazing with choreography,” said Mr. Carthas, who produced the shoot. He said that she and Ms. Eilish got along well on set, which is why Ms. Eilish felt comfortable enough to move around and pose the way that she did.

But even with a shoot that’s more minimalist in nature, a skilled photographer knows how to pivot based on the subject’s mood, as Ruven Afanador, a Colombian-born photographer known for his elegant, modern portraiture, did when he captured Ruth Negga for the December 2021 Great Performers issue. Ms. Negga, who was quite playful on set, ended up being photographed with a curly mustache, which her makeup artist had drawn on her face with an eyeliner pencil.

“Sometimes these take tremendous planning,” Ms. Ryan said of photo shoots. “And other times, someone has an unexpected, lovely idea we can build on.”