The biggest names in business can be tricky to photograph. They don’t always see the upside of publicity. They’re busy. And even if they do agree to sit for a shoot, they’re often reluctant to leave the office. Why wouldn’t they be? In their corporate cocoons, C.E.O.’s are in control. Out in the world, anything can happen.

Exactly.

“Our goal is to shoot outside the office whenever possible,” says Lisa Berman, photography director of Condé Nast Portfolio. “We want to show our subjects as people, not just businesspeople.”

Take Bill Ford. After we posed him alongside a painting of his great-grandfather Henry, he agreed to be shot inside his Mustang GT convertible. He even let photographer Kurt Markus tag along on his weekly hockey night. “I think he was embarrassed by my presence, as I was trying to do pictures just of him and not the team,” Markus says. Julian Dufort faced a different challenge when shooting hedge fund kingpin Ken Griffin and his French-born wife, Anne Dias Griffin, the driving force behind the couple’s newfound prominence in Chicago society. The location, a hard-hat area, was an addition to the Art Institute of Chicago that the Griffins are helping fund. Between takes, Anne and Ken sat with dueling laptops in the location van. Even farther away from the boardroom was Canadian dia­mond pros­pector Eira Thomas, who gamely donned a green gown and boots on a cold, rainy day in Vancouver, British Col­um­bia, for her shoot by Ralph Mecke.

But perhaps the toughest assignment of all was Jason Schmidt’s. After a 13-hour flight to Dubai, Schmidt had all of 10 minutes to photograph Sheik Mohammed bin Rashid al-Maktoum, the emirate’s ruler. Hoping for another opportunity, he asked to accompany the sheik on one of his horseback-riding excursions into the desert, but Sheik Mohammed’s demanding schedule—a last-minute trip to Abu Dhabi, lunch with Prince Charles and Camilla—stood in the way. Fortunately, Schmidt made the most of the time he got.

Unlike the Hollywood types Berman often dealt with in her previous job, at Vanity Fair, businesspeople are generally indifferent to her choice of photographer. “The only one they ever ask for is Annie Leibovitz,” she says. “She’s the household name.” And for good reason. From her stunning work for Rolling Stone in the ’70s to her portraiture in today’s Vanity Fair, Leibovitz has spent the past four decades shooting virtually everyone who matters in contemporary culture, shaping our view of celebrity itself and surely inspiring thousands to pick up a camera. For this issue, we asked her to photograph another giant of American magazines: Tom Wolfe. Leibovitz first photographed the writer for Rolling Stone in 1980 and has now shot him on three separate occasions. For this assignment, she posed him in his beloved 2003 Cadillac DTS, which is, of course, white. “It’s the most important thing in my life right now,” Wolfe says of his fully pimped ride, which even has white faux-suede floor mats with clear vinyl covers to keep them clean.

For our debut cover, we enlisted Scott Peterman, a fine-art photographer whose work has been widely exhibited, most recently at the Venice Biennale. Peterman, who lives in Hollis, Maine, has been working for years on his “mega­cities” project, in which he captures aerial views of uniformly geometric, anonymous cityscapes (often from a helicopter). For our cover, he shot Manhattan from the 86th floor of the Empire State Building, updating a famous Berenice Abbott photograph from 1932. “New York City is so recognizable,” he says. “It’s visually complex and a bit confused.” The resulting image is as celebratory as it is cautionary—and therefore seems like the perfect picture for our time.