In February 2012, Jeff Lipsky drove to Malibu, Calif., to photograph actor Sharon Stone. He brought a truckload of lighting equipment, but as he looked at the weather and surveyed the surroundings, he decided to rely on the sun instead. As an assistant splashed some light onto the star of Basic Instinct and Casino using a small reflector, Stone snapped, “You’re not lighting me with that!”

“She’s scary,” Lipsky says. But he pushed back. Nothing in his truck could create a nicer light than that day’s sun, he explained. “You need to trust me,” he said. “And she said OK.”

The story highlights two reasons Lipsky (CGS’86, COM’88) has become one of the most trusted and sought-after photographers in Hollywood: He’s able to put some of the world’s most famous and camera-weary subjects at ease, and he consistently creates stunning portraits. His photos of Stone blend the earthy tones of her shirt and sweater with the sunlight to create a golden glow.

If you’ve waited in a grocery checkout line or visited a movie theater in the past 20 years, you’ve seen Lipsky’s work. His celebrity and lifestyle photography has appeared in Vogue, Esquire, Outside and Vanity Fair. He’s shot Banana Republic campaigns and blockbuster movie posters. He’s photographed Kevin Hart, Brad Pitt and Taylor Swift.

Recent projects include photographing singer Michael Bublé for People and actor Rebel Wilson for the Sunday Times Magazine. He photographed football star Travis Kelce for a flu and COVID vaccine ad. He’s in the process of collecting his photos into a book about natural light.

“I always loved looking through magazines,” Lipsky says. “And my photo heroes were all portrait and lifestyle photographers—Herb Ritts, Richard Avedon, Gordon Parks, Bruce Weber and Annie Leibovitz.”

Lipsky has taken hundreds of thousands of photos. Millions, probably. Only a select few make it into print. Here are four photo shoots that helped to shape his style and define his career.

1. Daryl Hannah

Although Lipsky received a Nikon camera as a Bar Mitzvah gift—he developed his film in the family bathroom—his path to professional photography was long and circuitous. He studied advertising at COM and imagined a career with a New York City agency. But first, he wanted to go skiing.

After graduation, Lipsky drove to Telluride, Colo., where the chairlifts reach the edge of town and the slopes are open 200 days a year. He planned to ski for one season but stayed for 10. He gave snowboard lessons in the winter and led fly fishing trips in the summer.

Eventually, the ski bum began thinking about photography again.He got a job shooting for the Telluride newspaper and saved his tips from waiting tables to buy a high-end Hasselblad camera. And he began planning a leap into commercial and editorial photography, which meant moving to California and building his portfolio.

In 1998, a snowboarding client offered to help: “Daryl Hannah was kind enough to understand my plight,” he says. The star of Splash and Wall Street needed photographs for an upcoming profile in The Sunday Times and offered Lipsky the job. He’d begun assisting more established photographers in Los Angeles and was learning how to manage a complex shoot. For this project, there was no location scouting, no hair and makeup staff and no lights. He showed up at a ranch in Santa Ynez, Calif., with some black-and-white film stuffed into one pocket and color film in the other, and his new camera. “I barely knew how to load it,” he says.

What he did have, from years spent outdoors, was an eye for good light. And his goal for that day wasn’t much different from how he approaches celebrity shoots today. “I just wanted to capture her for who she was,” he says. With Hannah, that meant photographing her next to a horse paddock and in a barn. “She had a dirty T-shirt on and she was lying down in the stall, and the horse was just stepping all around her,” he says. “That’s who she is—she just is one with her animals.”

With the Hannah photos anchoring his portfolio, Lipsky began networking. One photo editor introduced him to another and, in 2002, he got his biggest assignment yet: a cover shoot with actors Paul Walker and Naomi Watts for Premiere, the now-defunct movie magazine.

2. Paul Walker & Naomi Watts

Premiere’s creative team gave Lipsky specific guidelines: He had to shoot Walker and Watts individually, on blue backgrounds, so the designers could create two covers for the 2003 “Sex & the Movies” issue. “I was nervous as hell and I never really liked the images,” Lipsky says.

With the images he shot for the magazine’s interior, he had more freedom. “I still hadn’t come into my own and figured out what my aesthetic was,” he says. But he did have the confidence to pack up his lights and take advantage of the beach house they had rented for the day. He photographed Watts leaning on a sun-splashed window and Walker driving a convertible.

“There’s a stigma about natural light in the photography world,” Lipsky says. “Some people think, ‘Oh, you don’t know how to light’ if you’re using natural light. But natural light is really hard to work with because of the timing.” To get the shot he wants, his subject has to be in the right place, at the right time, in the right weather conditions.

On that day in Malibu, Lipsky was establishing a style that has come to define his career—he just didn’t know it at the time. It’s bright and natural, and it’s a contrast from the way we typically see celebrities—as though he’s providing a genuine glimpse behind the costumes and makeup and special effects. “I looked back at that shoot and it has the same natural, organic vibe that I’m still doing today,” he says.

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3. Jason Momoa

For Lipsky, certain magazine assignments are significant bench- marks in his career. Vanity Fair, Vogue and the ESPN Body Issue were the places where he saw the work of photographers he admired, so they were the publications he strove to shoot for. “It was so superficial,” he says. “But it’s a validation of who you are as a photographer.”

As he made his way up to that level, he became more confident in his style—and how to achieve it. “Being a good photographer means you’re steering the ship. You want everything in your favor so that you can take better pictures,” Lipsky says. That means he’s scouting locations, choosing the wardrobe and picking his team, from assistants to hair stylists. Several weeks of preparation can go into a single shoot. But with all of those variables controlled, he can focus on the biggest challenge: getting his subjects to let their guard down.

The whole job of a photographer, from my point of view, is to make people feel comfortable and trust you. Without that trust, you don’t get good images.

Jeff Lipsky

His fun-loving personality emerges in unexpected places. Visitors to his website can play a silly game, dragging and dropping various hats onto an image of Lipsky, experimenting with how he looks in fedoras and beanies and baseball caps. A portion of his Instagram account is devoted to lighthearted self-portraits that give the impression that Lipsky is levitating.

He says that getting some subjects comfortable is as simple as playing the right music. For others, he has to get more creative. When he got an assignment to photograph the notoriously cam- era shy John Cusack, Lipsky organized a barbecue in a friend’s backyard, set up some photo backdrops, and invited the actor over. “Let’s hang out and take pictures,” he told him.

In 2018, Men’s Journal asked Lipsky to photograph Jason Momoa in a pond. He resisted. “That was the last thing I wanted to do,” he says. He didn’t want to be forced into creating an awkward connection between the actor and his Aquaman character—he wanted to photograph the person behind the character. Lipsky moved the shoot to Momoa’s property, where he photographed the star throwing axes, rock climbing and gardening. “He was comfortable,” Lipsky says. “I got much more material than I would have gotten in the water. It’s one of my favorite covers.”

4. Lady Gaga

In 2017, Lipsky received a dream assignment: archival portrait photographer for the Academy Awards. From 2017 to 2019, he was a fixture backstage, taking the official portrait of each winner.

It’s the antithesis of how Lipsky usually works because he has so little control. He’s limited to a small set, constructed under the direction of the Academy. It’s night, so he has to use artificial light. He doesn’t even know who he’s photographing until their names are read onstage, minutes before they walk into the makeshift studio. But the job is irresistible in other ways.

“I’m the first person they come to, even before they get their champagne. You get them in this intimate moment,” he says. “They’re all stunned. They’re all freaking out. Everyone in the world is looking for that person. It’s so much fun.”

For Lipsky, the gig meant reuniting with many stars he’d photo- graphed before. But in 2019, there was one person he was hoping to capture for the first time: Lady Gaga. The singer had been nominated for Best Actress and Best Original Song for A Star Is Born. She was the biggest star on an evening devoted to stars.

“We assumed we weren’t even going to get her,” Lipsky says. Oscar winners aren’t required to sit for official portraits, though most do. Lady Gaga went on to win Best Original Song and, after accepting the award, she made her way backstage: “Jeff, I want you to take pictures for me, for my family,” he remembers her saying. In the relative quiet of the studio, the significance of the moment began to hit her.

“The only thing I wanted from her was her true emotion,” he says. “And I caught her at her most vulnerable moment. She was just ready to cry. I let her eyes make the picture.”