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It all happened at the exact right instant when the South Beach renaissance coincided with the supermodel moment, creating a big bang in American publishing. Twenty years later, the Ocean Drive cover—those three words, now so illustrious— has become an internationally known symbol of beauty, glamour, and Miami-style sultriness. From the start, it was decreed that the cover would forego the provincial look of the “city magazine”—the shopworn best-bargains, top-hamburgers, and where-to-take-the-kids concepts that littered the genre—and instead embrace a sexy worldliness reflecting the city’s growing reputation as a hedonist hot spot.

Founding publishers Jerry Powers and Jason Binn changed the game with their premiere Claudia Schiffer cover, followed in short order by all the other one-named legends: Christy, Linda, Naomi. “It was a special time in Miami,” says photographer Scott Teitler, who shot Niki Taylor, Tyra Banks, and Bridget Hall, among others, for the cover. “There was so much potential. Ocean Drive was a big deal because it defined to the rest of the world a certain flavor that was distinctly Miami.

And that flavor—sexy, tropical, hip— drew throngs of visitors to South Beach. “The Ocean Drive cover was the greatest ad campaign known to any city,” says Glenn Albin, who served as editor-in- chief from 1995 to 2008. “We saw our issues as coconuts that floated the Miami Beach message around the world. And the cover was an industry standard, representing an optimistic glamour and sexy elegance.”

The publishing world took notice. Photographer Greg Lotus, now one of fashion’s most in-demand talents, captured icons like Stephanie Seymour for the magazine. “At that time, I was shooting most of the covers. Then I flew to Paris to meet [Italian Vogue Editor-in-Chief] Franca Sozzani. I showed her the Ocean Drive photos, and she immediately assigned me 10 pages to shoot,” he says. “Basically, I went from Ocean Drive straight to Italian Vogue.”

“At Ocean Drive, supermodels were our big-game cats,” adds Albin, now editorial director of Vault magazine. “ Jerry and Jason had relationships with Patrick Demarchelier, Francesco Scavullo, Antoine Verglas, and Marco Glaviano, and these were always wells we could go to. But my mission was to create original content and work with younger, edgier talent. Gradually, Ocean Drive became known as a content creator versus a procurer.”

As the ’90s progressed, celebrities began to appear, and a Jennifer Lopez or Elizabeth Hurley would alternate with a Heidi Klum or Cindy Crawford. Longtime creative director Carlos Suarez, now founder and creative director of Whitehaus Media Group, says, “We were getting some very timely celebs and actresses. You had to predict what movie or show was going to do well months in advance. Ocean Drive was growing up fast. People were surprised we put Pamela Anderson on the cover, but five months later, she was on the cover of W.”

By the early 2000s, the magazine was known as a key platform for rising as well as established talent, with Kirsten Dunst, Jessica Biel, Mena Suvari, Beyoncé, and Mila Kunis all in the spotlight. “Most of them knew Ocean Drive from their visits to South Beach,” adds Suarez. “And they all loved the oversize format and print quality, so it became easier to shoot with them. They felt safe because they always knew we needed a beautiful cover—save the crazy stuff for the other magazines.”

Occasionally, though, a more outré image would emerge. “Pushing for more controversial photography had its risks,” Albin says. “[PR guru] Liz Rosenberg agreed to give us an exclusive Madonna outtake. But it was so edgy, both Jerry and Sandi [Powers] just stared speechless at it for minutes when I unveiled it. It did look like I was playing a joke on our brand. And pairing Dahlen, the most artistic fashion photographer of the ’90s, with Gloria Estefan resulted in a makeover that no one expected Ocean Drive to engineer.”

As the Clinton-era bikinis receded (although never entirely), a new millennial streak of couture began to emerge. “As Ocean Drive evolved into such a success, it became increasingly easier to secure really special pieces for the covers—even and especially haute couture,” says Niche Media Fashion Director Laurie Brookins, who has worked with the magazine since the mid-’90s. “For example, when Eva Longoria did one of our anniversary covers, we secured Atelier Versace— that label’s haute couture. That entailed many calls and e-mails, but the effect was just stunning. And Emmy Rossum in Chanel haute couture was timed to when Karl Lagerfeld was bringing Chanel’s Cruise show to The Raleigh. That cover was really the essence of ethereal beauty.”

In 2004, Ocean Drive broke one of its essential mandates, but to great effect: Crossing the gender line, Shaquille O’Neal, then the Miami Heat’s resident superstar, became the first man to appear on the magazine’s cover. He was followed by Sean “Diddy” Combs, Dwyane Wade, Nacho Figueras, Enrique Iglesias, and, most recently, Olivier Martinez. “It was an honor to be among such great company,” Wade says. “And that cover shot exemplified what fashion means to me, incorporating bright colors against a few shades of gray. Style for me is about taking risks.”

Today, the magazine continues to strike a unique balance, with personalities like Gabrielle Union and Nicole Richie complementing top models such as Caroline Winberg and Elettra Wiedemann. “The heavy-hitter agents want their girls on our covers because they know it’s a great showcase,” Brookins says. “Irina Shayk’s agent said she was a girl to watch, so we put her on our swim cover two years ago. Sure enough, she became the next Sports Illustrated Swimsuit Issue cover.”

And the magazine’s immediately recognizable look has created one of the publishing industry’s strongest brand signatures. “The Ocean Drive cover is sexy, but in a really sophisticated way,” adds Brookins, “with glowing skin, blowing hair, and clothes that are very current and on-trend. We’re a city that loves color, so you might see more bright colors on our covers than in other cities. But isn’t that part of the fun of being in Miami?”

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