Written by By Wilfred Chan, for CNN Hong Kong

Few artists are lucky enough to work for legendary Hong Kong film director Wong Kar Wai. Even fewer are brave enough to defy him.

Wing Shya has done both. The first time he worked as Wong's exclusive set photographer, he became so entranced by scenes that he shot entire rolls of film that were unfocused, off-center, or riddled with technical errors.

"Of course Wong Kar Wai yelled at me," Wing recalls. "Imagine some guy coming to photograph Leslie Cheung and everything comes out blurred. You'd wonder, what's this guy's attitude?"

But he stood behind his work —"I said, hey director, this is full of feeling!"— and when Wong accepted it, he knew he was onto something.

"Things are only mistakes if you think they are," he explains. "Technique, don't even worry about it. Just focus on your heart, and everything else will work out."

Hong Kong's moody aesthetic

Underneath that simple mantra lies a tenacious drive. Today, Wing is one of Asia's most iconic photographers, known for his raw, smoky images from the golden era of Hong Kong cinema. He's helped to define a look that belongs uniquely to this former British colony, and inspired countless imitators.

But he started as a restless young design graduate in Canada, who decided to return to Hong Kong after classmates ridiculed the art from his hometown.

"I'm going to do something to help," he recalls thinking. "I wanted to come back and create something good."

Back in Hong Kong -- then a booming metropolis under British rule -- Wing became fascinated by the city's charming visual aesthetic.

"There was a mood. I saw how everything was loud, lit up, like a collage of life. To be imperfect, that is Hong Kong: A place filled with little mistakes. When you add it all up, it's really beautiful."

This is the tender idea that runs through the artist's work, from his time under Wong Kar Wai to a subsequent solo career as an art and fashion photographer that's spanned two prolific decades. Inspired by both cinema and city, Wing Shya's photographs hint at the mysteries of time gone by: his models' faces are washed in nostalgic color, obscured by shadow, often wearing expressions of longing or hidden sentiment.

In one classic image, actress Shu Qi rides backwards atop a chromed motorcycle piloted through Hong Kong by a cigarette-toting Daniel Wu, their hair whipping in the wind, a cross-processed fantasy of youthful anomie.

In another unforgettable shot, supermodel Du Juan stares through a softly lit fish tank, lost in a pastel-colored soliloquy.

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The secret? Wing pens film scripts for his editorials -- every photograph has a complete, fictional backstory, which he won't reveal. The shots are set up and lit by some of Hong Kong's finest film crews. "When you look at a photograph, you should see a life there," says Wing. "I've been playing with these methods for years."

Will Hong Kong be this cool again?

Yet today, Wing's photos feel like throwbacks to an impossibly beautiful bygone era. Just shy of two decades after the city's handover to Chinese rule -- the same time Wing did his first assignment with Wong Kar Wai -- Hong Kong is in a slump.

Its film industry's glory days, immortalized by Wing's photographs, have long faded. Now the city is known for its worsening political crises and flatlining economy. For many artists, the fruitful mix of tension and anticipation during the handover has given way to a stifling hopelessness.

In a sense, Wing belongs to a defunct period of nostalgic Hong Kong artists. But the photographer sees decline as something to be fully embraced.

"When a city is molding, something new must sprout," he says. "It's only when the mold is this wet that we'll be able to grow some new mushrooms."

Recently he's been shooting conceptual art videos. In an upcoming piece, he films over a hundred topless men brawling in a Beijing warehouse — at a frigid 21 F (-6 C). The idea is that in letting the conflict discharge and defuse, he'll be able to convey the "meaning of love."

Meanwhile, he teaches art workshops and crawls social media, hoping to discover emerging talent who will create something completely novel to reflect the changing times.

"The fall is the fun part. I'm waiting for the moment -- after we pass a certain point, that's when the new things blossom."