Annie Leibovitz and Tina Brown on 'Pilgrimage,' Photography, and Vanity Fair

The renowned photographer talked to Tina Brown about her new book and their days together at Vanity Fair.

Annie Leibovitz sure is charming. She has persuaded some of the most famous people in the world to take off their shirts, pose in a bathtub of milk—or grace a magazine cover nude and eight months pregnant.

“She’s a master of the follow-up—a relentless perfectionist,” says editor Tina Brown, who hosted a conversation with the celebrated photographer at a breakfast series sponsored by Credit Suisse and Newsweek/The Daily Beast.

Leibovitz was there to discuss her latest collection, Pilgrimage, which is filled with subjects she didn’t have to charm at all. Traditionally a portraitist—and considered by many to be the finest of her generation—Leibovitz instead turned her lens to locations and objects that make literary and cultural giants seem human. An image of Emily Dickinson’s white brocade dress speaks nearly as much about the woman as her poems do. There’s a pair of gloves that were nestled in Abraham Lincoln’s jacket the moment he was shot. And she snapped Sigmund Freud’s couch looking inviting and intimidating. “With this book, you sort of go on a treasure hunt,” said Leibovitz.

What culminated in an enlightening hodgepodge of artifacts began as a “replenishing, powerful journey,” she said. In 2009, before she began the project, Leibovitz became embroiled in a legal and financial crisis. (“I actually came here today because I want to get refinanced,” she joked early on to the crowd of Credit Suisse executives.)

During the conversation with Brown, Leibovitz recalled one low point during her financial distress. She planned a trip to Niagara Falls for her children to escape from the daily routine, but her credit card bounced when she tried to check into the first hotel. “We went down to another hotel, woke up in the morning, and this is what we saw when we opened the curtains—a brick wall.” Hitting that moment, she said, was a punctuation mark on a disastrous year. “I looked at Niagara Falls,” she said. “And thought, is it a beginning or an end?”

To shake off her financial doldrums, Leibovitz decided to create a cultural bucket list of a dozen places she always wanted to see: the homes of Dickinson and Annie Oakley, Thoreau’s cabin at Walden Pond, and others. Asked if she was drawn to these figures because of her partner, the late literary critic Susan Sontag, Leibovitz said, “I’m not too sure what I was doing [when I started]. But I knew that Susan had an influence on me. I never would have been drawn to [Virginia] Woolf if not for her.”

Pilgrimage is a glimpse into what fascinates the legendary photographer. The collection reveals as much about process—“This is like a note-taking of my other work,” she said, referencing the intense background research and location scouting that goes into a shoot—as about Leibovitz herself.

It’s a departure from her previous books thick with glossy celebrity portraits, which she says made it a tough sell for her publisher, Random House. Pictures of disparate locations around the country and quirky memorabilia don’t exactly fly off the shelves of Barnes & Noble. Yet it many ways, the volume acts as an appropriate homage to her career, which was forged for many years alongside Tina Brown at Vanity Fair and The New Yorker.

Brown recalled her early days at Vanity Fair and seeing Leibovitz’s shot of Whoopi Goldberg sprawled in a big bathtub of milk. She splashed the image inside her first issue. Many Leibovitz covers followed. “Tina worked me to death,” the photographer said with a smile. But Leibovitz works her subjects in the same way. A shoot with Annie Leibovitz is carried out with precision, “like planning a drone attack,” said Brown. “I was always very impressed with the incredible care and passion and detail in her work. She treated the smallest assignment as a very large one.”

Sometimes the very large ones are talked about for 20 years. Her Demi Moore portrait for Vanity Fair heralded a new era of sexy motherhood, while offering a new answer about what to wear when you’re expecting: nothing. “No one in their right mind would put that on the cover,” said Leibovitz. Brown admitted they spent time sweating circulation numbers before the issue hit newsstands, yet the image was an instant classic, and has since been mimicked by everyone from Claudia Schiffer to Britney Spears.

Leibovitz also relived some of her more controversial moments—there was, for instance, the shoot in 2007 with Queen Elizabeth, after which the BBC ran footage indicating she walked out in a huff. (She most certainly did not.) Some dared to question if an American photographer could capture royalty. In response, Leibovitz says, “If you were an English photographer, you were throwing her away. You weren’t really taking [the queen] seriously.” Instead of trying to “undo” the most famous woman in the world by catching her off guard, Leibovitz presented her as herself—and was rewarded with a hint of vulnerability. At one point during the session, Leibovitz remembered, the queen became very quiet before saying, “[My sister] Margaret is a much better poser than I am.” Suddenly she was human.

While there’s a level of intimacy that must be reached with a subject, Leibovitz takes care to draw certain lines about her process. “I don’t think it’s my job to make anyone feel comfortable,” she said. But when her subjects do feel at ease, what a windfall. Take the Tiger Woods shoot for Vanity Fair. His ripped abdomen and seductive glare graced the cover after his sex scandals, though the shoot was done before. “I knew he was obsessed with working out,” she says. “He loved the shoot so much because it was just him working out for three hours.” Leibovitz managed to uncover the real man behind the clubs. Like any great journalist and artist, she has a knack for determining and illuminating details worthy of attention—even before they’re a story.

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That level of careful attention is what makes Pilgrimage so compelling. Leibovitz claims she’s not giving up portrait work altogether, and she’s always seeking something more. When asked by Brown if there is one photo that defines her career, she referenced the great photojournalist Henri Cartier-Bresson. He lived for the “decisive moment,” she said, “and I’m sort of looking for what comes after the decisive moment.”

There is one image that speaks louder to Leibovitz than others—and inspires her to continually do more. “There is a photograph [I took] of my mother, which is a great, great portrait, because the camera is not there. She’s looking beyond the camera. That one raised the bar.” Here the typically private photographer nearly teared up. “I can’t get to that kind of picture in my everyday work, and you shouldn’t be presumptuous to think you’ll get that every time … but it’s something to shoot for.”