Why Vanity Fair’s Caitlyn Jenner Cover Became Instantly Iconic

Plus, legends weigh in on other memorable mags

Headshot of Emma Bazilian

Vanity Fair made headlines this month with the release of its July 2015 cover, featuring a photograph of Caitlyn Jenner shot by Annie Leibovitz. It didn't take long for the image to become a viral sensation—or for people to begin speculating that it had earned a spot in the pantheon of "iconic" magazine covers.

But what is it, exactly, that makes a cover iconic? We spoke to four of the people behind some of the industry's most-lauded covers—Vanity Fair editor Graydon Carter, legendary Esquire art director George Lois, Rolling Stone managing editor Will Dana and former Bloomberg Businessweek creative director Richard Turley (who is now svp of visual storytelling and deputy editorial director for MTV)—to find out.

One thing everyone agreed on is that there is no magic formula for a successful cover. However, there are a few things that all iconic covers have in common. "It's a bit like capturing lightning in a bottle," said Carter. "A great idea and simplicity in execution help. An iconic cover also has to tell you something about the age we're living in. And the best ones don't look like any cover you've seen before."

George Lois posed Muhammad Ali as Saint Sebastian.

Memorable covers also criticize—and even try to change—the current culture, added Lois, who was responsible for famous Esquire covers showing Muhammad Ali as Saint Sebastian, a young woman in a trash can (the cover line read "The New American Woman: Through at 21") and various jabs at the war in Vietnam. "[Good magazines] don't brand themselves because they have a famous person on the cover or because the blurbs are hot stuff; they brand themselves by showing people that they are intelligent and can speak to the zeitgeist," said Lois.

Even when the components are all there, it can be difficult to tell how readers will ultimately react. In the case of Rolling Stone's Boston Bomber cover, which was hastily assembled just a few days before the issue's close (and wasn't even intended to become a cover when the story was first assigned), "I didn't anticipate the backlash," said Dana. "Certainly I thought it would be controversial, but I didn't think it would rise to the level that it did … [With social media], the volume gets turned up so much."

The explosion of social media, of course, has helped magazine covers have a wider impact than ever before. Turley, in particular, credits Twitter, which was just hitting the mainstream when he joined Businessweek in 2010, with helping his boundary-pushing Businessweek covers gain wider acclaim."We were early adopters in making sure that the covers were available on the Internet and that we tweeted them out," he said. "An image that you could share with your friends to say, 'Look how smart I am, I follow this'—that kind of currency became more and more important."

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At the same time, social media has also made it tougher for covers to stand out, said Dana. "It's hard to break something like that on a magazine cover nowadays because social media gets there so much before you," he explained. "Something like Caitlyn Jenner where there's that same level of hype and surprise and the sense of something being revealed—that's not something that comes along very often."

Still, in an age where print is being constantly subsumed by digital, the impact of a cover like "Call me Caitlyn" proves that the magazine still holds an important place in the media landscape, regardless of whether it's being consumed on a newsstand or in an Instagram feed.

"Magazines have such an opportunity every month to knock you on your ass, to really get you excited," Lois enthused. "What a canvas a magazine cover is!"

@adweekemma emma.bazilian@adweek.com Emma Bazilian is Adweek's features editor.