In keeping with the times, Leibovitz’s early work focused on politics and rock and roll—Nixon’s resignation, Sly Stone. By the late seventies, she had begun to display a lighter, more comic style, like painting the Blues Brothers’ faces blue and posing Bette Midler, star of The Rose, atop a bed of roses. Later, at Vanity Fair and Vogue, she became known for idealized, heroic portraiture. Leibovitz has an uncanny ability “to make boring white men who have desk jobs look epic,” says Graydon Carter. “She shot a photo of me where I looked like I was James Dean or something,” says Quentin Tarantino of his 1994 portrait. “And I’m a guy who doesn’t look like James Dean.” “These pictures are how I will look in heaven,” author Brett Leveridge wrote of a book-jacket photo that Leibovitz shot. Unlike her hero, Avedon, Leibovitz seems unwilling to shoot an unflattering portrait. “Annie does not share the ruthless nature of editors and writers,” Leibovitz’s friend the book editor Sharon Delano says. “Her enterprise is essentially good-natured.”
From her earliest days at Rolling Stone, Leibovitz demonstrated a near-crippling fear of not coming back with the shot. Lloyd Ziff, a former Rolling Stone designer, remembers Leibovitz being sent out to get a simple image of the world’s oldest Coke bottle kept in some little museum. “She took 300 to 500 Polaroids of it,” he says. “I don’t care who you are or what levels of energy or patience you have,” says Carter, “Annie will wear you out. She’ll beat you. Because she’ll have more patience than you do. And she will eventually get her shot.” Arnold Schwarzenegger still jokes about flying through a blizzard in a helicopter, then nearly freezing to death for the 1997 Vanity Fair cover image of him on skis on a mountain top in Sun Valley, Idaho.
Leibovitz once described her portraiture method as “get ’em somewhere where they’re bored shitless and there’s nothing to do except take pictures.” From there, she would work her subjects to the point of exhaustion, a state that could lead to revealing moments of vulnerability. For a 1981 Rolling Stone shoot, William Hurt sat in his parents’ house in New Jersey one afternoon. At seven o’clock the next morning, Leibovitz was still shooting the actor, who by now was wearing only a pair of briefs. Getting her subjects to disrobe became such a familiar gambit that by the time Leibovitz moved to Vanity Fair, she vowed to “shake this reputation as the girl who gets people to undress.” That never happened, of course. Some of her most talked-about shots at Vanity Fair were the naked-and-pregnant 1991 Demi Moore cover, the 2006 Hollywood Issue cover with Tom Ford hovering lasciviously over the nude Keira Knightley and Scarlett Johansson, and the 2008 shot of 15-year-old Miley Cyrus covered only in a sheet.
Photographers are typically paid a fee for their work, plus expenses. The client, whether it’s a magazine, advertiser, or individual, stipulates an expense budget that the photographer must operate within. From the start, Leibovitz’s perfectionism led her to pay little or no attention to budget restrictions, and she spent money recklessly, losing cameras, accruing parking tickets, and even abandoning rental cars.
In the early Rolling Stone days, Leibovitz was a sort of little sister to the magazine’s staff, smoking, drinking, and hot-tubbing alongside Wenner, Thompson, and the others. In 1975, against Wenner’s advice, Leibovitz accepted a two-month gig as the Rolling Stones’ official photographer for their Tour of the Americas. Everyone drank and got high on a Stones tour, of course, but when Leibovitz returned to San Francisco, her appetite for cocaine had become more than merely recreational. Robert Draper’s Rolling Stone Magazine: The Uncensored History paints Leibovitz as a full-fledged drug addict, who twice overdosed. She may have even hocked some of her cameras to pay for drugs, he writes.
Leibovitz left Rolling Stone for Vanity Fair in 1983. Her reputation for dubious money management apparently traveled with her. “Getting her accounts at rental houses and film labs was a struggle,” says Andrew Eccles, now a highly regarded photographer who worked as Leibovitz’s assistant from 1983 to 1986. “I had to get people to believe me when I said it wasn’t the old days anymore. People would actually get paid for their equipment.” Because of her credit issues, Leibovitz was forced to deal almost exclusively in cash. In 1987, American Express offered her a plum ad campaign. Ironically, Leibovitz’s application for a card had been denied many times. After the ad agency found out she’d lost an envelope containing several thousand dollars in a phone booth during their shoot, strings were finally pulled to get her a card.