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The Best Portrait Photography of the Last 20 Years

A face is like a work of art—it deserves to be preserved by the grand tradition of portraiture.

Miss Rosenby Miss Rosen
Photo: Yayoi Kusama – George Clooney for W magazine.

Perhaps there is no subject as compelling as the human face, nothing we gaze upon with so much quiet curiosity. The great portrait painter Don Barchardy told me that the reason it is considered rude to stare is because, “The face tells too much.”

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The portrait, then, is a window into the soul: an image of how the person wishes to be perceived in combination with how the artist views who they are. We like to believe that by looking upon a person’s visage, we can gain knowledge of the being that lives within, the mind and heart that makes them a singular individual. In celebration Crave has compiled the best portrait photography of the last 20 years.

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Mario Testino: Princess Diana for Vanity Fair

Just two months before her death in September 1997, Mario Testino’s portrait of Princess Diana appeared on the cover of Vanity Fair, along with an interview that revealed the maturity and growth of a woman with a troubled past. From the cover she radiated a kind of inner bliss, a sense of peace that has come in rebuilding her life after the divorce. She had crested, reaching new heights and filled with new hope, finding the happiness that had eluded her throughout her life.

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Yayoi Kusama: George Clooney for W

In December 2014, George Clooney appeared on the cover of W magazine, in a portrait created by no less than the legendary artist Yayoi Kusama. Here we see the artist do something powerful and new: create a tableau for her work that combines art, portraiture, and photography in astounding new ways. At the same time, Clooney goes beyond his comfort zone, revealing a side of himself that goes beyond the said and known.

New York-Best News and Politics

Amanda Demme: Cosby: The Women for New York

Most rape accusers never show their face, knowing how quickly the media and public will attack them for daring to come forward with their story. In a world where “he said/she said” continues to drive the narrative, most people keep the stories to themselves lest they have to go through a second ordeal. In the case of Bill Cosby, dozens of women finally spoke out, and in doing so, they revealed their names and faces to the world on the cover of New York magazine In July 2016.

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Yu Tsai: Serena Williams for Sports Illustrated

When Serena Williams appeared on the cover of the December 2015 edition of Sports Illustrated as Sportsperson of the Year, many were big mad about the one of the greatest athletes of all time posing provocatively upon a gold throne. Williams broke the mold and turned it to dust, making history in the process and showing pride of self. Williams was the first solo woman to make the cover since 1983—and she took control, crafting an image of domination she was ready to show the world.

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Nadav Kandar: Donald Trump for TIME

In 2016, TIME magazine named Donald Trump “Person of the Year” and crafted a cover image by Nadav Kandar that bespoke things to come, things unknown and lurking like the shadow cast behind him. Every detail of the image was perfectly crafted, from his pose looking back over his shoulder to the lightly tattered chair in which he sits. It’s a foreboding image that suggests that what we are experiencing in the first six months of 2017 is a harbinger of things to come.


Miss Rosen is a journalist covering art, photography, culture, and books. Her byline has appeared in L’Uomo Vogue, Vogue Online, The Undefeated, Dazed Digital, Aperture Online, and Feature Shoot. Follow her on Twitter @Miss_Rosen.