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Best Celebrity Photography of the Last 20 Years

Making a celebrity look fresh is a talent that only the best photographers have mastered. Crave showcases the crème de la crème.

Miss Rosenby Miss Rosen
Photo: Steven Klein: Rihanna for W Magazine, September 2016.

In recent years, celebrities have become so ubiquitous that it’s hard to make them look fresh. Even when they switch things up—be it their hair, outfits, or romantic partners—the threat of overexposure and boredom looms large in those who constantly stay in the public eye.

Also: Best Music Photo Books of the Last 20 Years

A great photographer can see past all this: past the superficialities of hype, appearance, and the latest press junket. A master will use the camera to delve beneath the surface of the soft supple flesh in a search for the eternal, ethereal soul that lies within. Crave celebrates those who do it best with this tribute to the best celebrity photography of the last 20 years.

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Paolo Roversi: Rihanna for i-D

For the pre-Spring 2015 issue of i-D, Italian photographer Paolo Roversi photographed Rihanna with elegant and eloquent simplicity. The music and fashion icon pared things down to a simple look of braid and hoop earrings that evoked a timeless Buffalo Gal vibe. In this photograph, Rihanna, who excels at crafting an image that pushes the edge, is pure energy waiting to explode.

Roversi, who has began working professionally in 1970, uses a timeless approach to portraiture to craft a series of photographs that evoke the paintings of yore. In Rihanna, he found the perfect subject for his aesthetic, giving us a glimpse of island gal who rules the planet.

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Bruce Weber: Bill Murray for Vanity Fair

Best known for the Abercrombie & Fitch and Calvin Klein campaigns that showcase young, nubile flesh scantily clad and enjoying the pleasures of life, Bruce Weber switched it up for the November 2015 cover of Vanity Fair, with a fully clothed Bill Murray tiding a dinosaur float in someone’s backyard pool.

Murray has been a Hollywood staple ever since he first gained exposure in 1977 on Saturday Night Live, which catapulted him to being one of the top comedic actors of the 1980s and ‘90s with leading roles in Caddyshack, Ghostbusters, and Groundhog Day, before going on to try his hand with drama in Lost in Translation, Moonrise Kingdom, and The Grand Budapest Hotel. By 2015 , he was ready to hear the sound of laughter again, as the cover image attests—he hasn’t lost his sense of the sublimely absurd.

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Mario Testino: Naomi Campbell and Sean Combs for British Vogue

For the October 2001 issue of British Vogue, Mario Testino paired a virtually topless Naomi Campbell with a fully suited Sean Combs. The effect was perfect as their friendly embrace signaled the warm welcome the Bad Boy owner was getting by the fashion establishment. While models have always been welcome into the celebrity circuit, it’s impossible to say that it cuts both ways, as most celebrity designers quickly fall from grace. But Combs brought something few had ever seen before—his business savvy and determination that perfectly matched that of Seventh Avenue. This image signifies a major moment of transition as actors and performers began to take the place of models on the cover of major fashion magazines.

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Kurt Iswarienko: Gael Garcia Bernal for Flaunt

Advertising and celebrity photographer Kurt Iswarienko shot Gael Garcia Bernal for the November 2008 cover of Flaunt magazine. The Mexican actor, director, and producer, best known for his performances in The Motorcycle Diaries and Y Tu Mama Tambien, becomes transformed into a work of art himself, as a vibrant layer of kaleidoscopic lights vibrate around his face. The image is instantly cinematic and intense, invoking an ethereal energy that goes far beyond the traditions of celebrity portraiture.

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Alexandra Gavillet: Rae Sremmurd for The Fader

In June 2016, Alexandrea Gaviillet set the world ablaze with her stunning portrait of Rae Srremmurd on the cover of The Fader’s summer music issue. Bthoers Jxmmi and Swae Lee appeared together wearing nothing but tattoos, against a hazy backdrop of lilac, lavender, and blues. It was the perfect image to capture the times, breaking free from the hyper-masculine depictions that had ruled Hip Hop since the 1980s.

In the year that saw Moonlight surprise the world as the Academy Award winner of the Best Picture, Gavillet’s photograph perfectly described the complexity and nuance of black masculinity in the twenty-first century. It can not be described by stereotypes of the past, but rather through liberation from all that has come before to fully embrace the joys and beauty of life.


Miss Rosen is a journalist covering art, photography, culture, and books. Her byline has appeared in L’Uomo Vogue, Vogue Online, Whitewall, The Undefeated, Dazed Digital, Jocks and Nerds, and L’Oeil de la Photographie. Follow her on Twitter @Miss_Rosen.