Four Epiphanies That Helped Me Understand What Makes a Powerful Portrait

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Taking someone's portrait has always frightened me.

For years, I’ve been haunted by the seemingly straightforward question “What makes a good portrait?” As a documentary photographer, I specialize in what can be broadly described as reality. But I don't subscribe to the common notion that a portrait can capture the “true essence” of a person. Any claims to such “authenticity” make me instantly suspicious.

Richard Avedon famously said that “All photographs are accurate, none of them is the truth.” While that may seem like a cynical statement, to me it sounds freeing. It extricates posed portraiture from the realm of pure representation and gives the photographer room to play and dream. Avedon's provocative photographs first seduced me into this unfamiliar, daunting genre. But for a long time I fumbled blindly while looking for that elusive formula that makes for a captivating portrait.

All the while, I obsessively collected examples of images that stopped me in my tracks. In trying to understand what works about each one, I have, in bits and pieces, amassed a collection of tiny epiphanies.

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In 1987, the German photographer Thomas Ruff made a series of large-scale passport style portraits, erasing any attempt at gaining insight into the sitter’s personality. It was a self-conscious exercise to disconnect portraiture from the narrative of capturing someone's soul. When I first saw them, I thought they were just bad, boring portraits. But these images helped me recognize the bare, unadorned surface of this genre without any of the elements of fantasy or empathy that photographers usually impose on their portraits. The startling lack of individuality turns Ruff's portraits into a series of blank slates (and as such they are successful, interesting even).

Which brings me to Epiphany #1.

A portrait is a fantasy. When the fantasy succeeds, it activates the viewer's imagination, triggering empathy and giving an illusion of insight into the subject. I can be fairly suspicious of the genre — a bad portrait is like a puppet show where all I can see is the strings — but a great portrait breaks right through my cynical shell and fills me with wonder.

Irvin Penn's iconic photograph of Picasso does just that. Penn was given 10 unwilling minutes by the painter, who tried to deflect him by putting on a theatrical cape and hat. Penn masterfully worked around these constraints by accentuating the burning stare of one lit eye and the sculptural contours of the hat while throwing the rest in deep shadow. The result is an intense, unsettling portrait that uses all the elements to activate our preconceptions about the artist's fiery, enigmatic nature.

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Epiphany #2.

A good portrait exists in the gap between how the subject wants to be seen and how the photographer sees the subject. It's a gap filled with tension, a push and pull of the sitter's desires with the photographer's intention.

Does it matter what Picasso thought of Irving Penn's photo? How much say should a subject have in the final outcome? In one extreme case of the subject's dissatisfaction, Winston Churchill hated his portrait by Graham Sutherland so much that his wife incinerated the painting.

The photographer doesn't need to honor the exact persona the subject is trying to project and risk the portrait becoming sycophantic, but there should be a certain level of trust where the sitter is not ridiculed or made to look grotesque through the use of light and angles. I have seen that happen too often over the last few years in our highly polarized political climate. Nadav Kander's portrait of Trump for the cover of TIME avoids the trap of the photographer becoming an executioner. Whatever his personal biases, he treated the former President with the dignity that should be afforded to any and every subject. Yet the photo is anything but congratulatory. Trump's gaze is penetrating and chilling. The shadow on the left side of his face, the half turn of the body and the blue tones of the image all reinforce a feeling of foreboding. I find this portrait masterful.

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Epiphany #3.

A portrait is less about capturing someone than about creating something. I am being a bit cheeky with this, but this subtle difference is where the fun begins. The photographer manipulates all the elements at their disposal — the subject's appearance, clothing, mood, interaction, as well as location, light, angle, tone ­— to make a work of fiction. The final work becomes more about the photographer's intention than the tangible reality of the sitter.

For this image, Pari Dukovic rebranded Kim Kardashian as a Byzantine Madonna. The portrait is a closed loop — an icon transformed into an icon. She is luminous, otherworldly and impenetrable. Kim is a professional image manipulator, working with an army of stylists, make-up artists, photographers and retouchers to protect the fortress of her projected persona. No portrait would make me understand her better on some deeper, more intimate level. Yet, whoever the “real” Kim Kardashian is, it is absolutely irrelevant to this image of her. As I scan Kardashian's ecstatic face, I cannot help but be seduced.

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Epiphany #4.

The new frontier of virtual portraiture.

This portrait of the writer Susannah Breslin by Nikola Tamindzic felt immediately uncanny, though at first glance I couldn't pinpoint why. Susannah appears both confined and cozy inside her small bathtub. Though her arms wrap around her body in a way that could read as modest, the gaze is assertive and piercing. But what gives the portrait a hint of Alice in Wonderland is the position of the camera itself, eye-level and so close to the subject that it feels like we are in the tiny room with her. Nikola managed to create such an intimate presence by being physically absent. Susannah was alone, posing for a smartphone while the photographer talked her through the shoot. The result is a strange, emotional portrait. For me, it was an image that showed just how powerful the new medium of virtual photography can be when used with intention.

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For Part 2 of Understanding Portraits, I will go deeper into virtual photography and how it led me to a personal breakthrough in my own work.

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