As the longtime editor in chief of Vanity Fair, Graydon Carter was accustomed to big expenses: chauffeured town cars, five-star hotel stays, writer salaries that stretched into the mid six-figures. But in early 2001, he wondered if he had gone too far.

Annie Leibovitz, the magazine’s chief photographer, had run up a $475,000 bill on a cover shoot involving 10 world-famous actresses — Nicole Kidman, Penélope Cruz, Sophia Loren — and an elaborate stage set, complete with a mantelpiece and a genuine John Singer Sargent painting, which was flown from Los Angeles to New York to London. (“It was like Vietnam, the expenses,” Mr. Carter recalled.) Now, he needed to tell his boss, S.I. Newhouse Jr., the billionaire owner and patron of Condé Nast, about the latest line item on his tab.

“I do have to talk to you about something,” Mr. Carter said as the men sat down for lunch. “It’s a good-news-bad-news situation.”

“What’s the bad news?” Mr. Newhouse asked.

“Well, I think we just shot the most expensive cover in magazine history.”

A pause. “What’s the good news?”

“It looks like a $475,000 cover.”

It was the equivalent of roughly $850,000 today. Mr. Newhouse was fine with it.

At its 1990s and 2000s peak, Condé Nast captivated tens of millions of readers with its glossy manuals to the good life: Vogue and GQ for fashion, Vanity Fair for celebrity, Gourmet for food, Architectural Digest for real estate. Editors like Anna Wintour, Tina Brown and Mr. Carter were the ultimate cultural gatekeepers, venerated and feared.