Rooftopping: Perched on Top of Skyscrapers to Photograph the City Below

Rooftopping sneakers
Image: Tom Ryaboi
Tom Ryaboi’s vertigo-inducing “rooftopping” take on Toronto

The legs dangling so casually off the top of the building highlight – to incredible effect – the sheer drop falling away beneath them. Just looking at this shot makes us feel dizzy, and we wonder how anyone could do what Tom Ryaboi does. Ryaboi is a photographer at the forefront of a trend called “rooftopping,” which involves climbing ridiculously high buildings and nonchalantly leaning over the edge to take photos.

Rooftopping with mask
Image: Tom Ryaboi
Balance has never been so important.

Ryaboi developed a compulsion for climbing pretty early. “My father says I climbed and sat on the fridge before I could walk,” he tells us. “I’m not sure what drove me to climb things, but as I entered my teens it’s something I lost interest in, or maybe I became interested in other things.”

Rooftopping climbing ladder
Image: Tom Ryaboi
I can see my house from here!

One of the “other things” that interested Ryaboi was photography. “In my twenties, when I picked up my first camera, I went on a ten-month trip from Canada to Argentina and I fell in love with capturing images. The camera really became an extension of myself,” he explains.

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Rooftopping view down skyscrapers
Image: Tom Ryaboi
All those lines of windows highlight just how many stories up this photo was taken from.

Ryaboi’s forgotten passion for climbing and his burgeoning interest in photography came together by chance in April 2011. While snapping street scenes in his hometown of Toronto one evening, Ryaboi came across a deserted construction site. The gate to the site wasn’t shut, so he entered the unfinished building hoping to get some good sunset shots from up high. “When I got to the top and opened the door to the roof I got an instant rush of adrenaline, like I just opened the door to a secret world of wonder,” wrote Ryaboi on his blog.

Rooftopping looking down skyscrapers
Image: Tom Ryaboi
The illusion of movement in this shot is unsettling.

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“I was really inspired by what I saw when I got to the top of the building,” says Ryaboi of that first rooftopping experience. “Watching the city move about, you start to ponder what it means to live in this mega urban setting and how we are all connected, yet we are all very detached.” According to Ryaboi, The Dictionary of Obscure Sorrows came up with the noun “sonder” to capture this feeling, which it describes as “the realization that each random passerby is living a life as vivid and complex as your own.”

Rooftopping looking through buildings
Image: Tom Ryaboi
The lights below glow an eerie shade of blue in this photograph.

After that fateful April 2011 evening in Toronto, Ryaboi was hooked. “Traveling, rooftopping and taking photos have been an integral part of my life since then,” he explains. From that moment on, Ryaboi always had an eye out for something to climb when he was on the streets. “Every building I walked by was now a potential target. I was sizing up the elevators, fire escapes, security, entrances and exits everywhere I went. Even in my sleep I was dreaming of roofs,” he wrote on his blog.

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Rooftopping looking down side of building
Image: Tom Ryaboi
This shot is so high up that it’s hard to make out a lot of the details below.

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Ryaboi had been actively rooftopping for half a decade when he and some fellow rooftoppers finally managed to ascend a particularly tall building in Toronto’s financial district that they’d been trying to climb for some time. It was this climb and subsequent photo shoot that first brought Ryaboi and his rooftop photography to the world’s attention – in particular, the arresting image of the dangling legs shown at the beginning of this article. A year after that incredible shot, Ryaboi told photography website 500px.com that he was still receiving requests for the photo.

Rooftopping sitting on scaffolding
Image: Tom Ryaboi
The more precarious the perch, the more arresting the photograph.

Although Ryaboi is one of the best-known recent proponents of the trend, he didn’t invent rooftopping. In 2011 a Russian teenager named Marat Dupri published his own daring rooftop photos, although he called the daredevil activity “skywalking.” Indeed, there are even famous records of photographs being taken from skyscraper roofs way back in the 1920s. Online, the word “rooftopping” has been traced back to a March 2004 post on Scottish urban exploration website The Hidden Glasgow.

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Rooftopping black and white
Image: Tom Ryaboi
Everything looks peaceful from up here.

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Rooftopping has several alluring elements for daring photographers and urban explorers. Firstly, there’s the prohibited nature of climbing to the restricted rooftops. The buildings, like the unnamed Toronto skyscraper Ryaboi scaled to get his famous shot, may be guarded by security. Then there’s the danger involved in moving about at such heights – which is intensified when it involves leaning over the edge. Of course, to more intrepid explorers, this only serves to make it more exciting.

Rooftopping street from top
Image: Tom Ryaboi
Some architectural features take on whole new dimensions from these heights.

However, the biggest attraction of rooftopping has to be the spectacular photographs. There aren’t many activities that can offer the same breathtaking views of the city or capture the astonishing perspectives and sheer drops to street level that these photos deliver. They give us a very different vision of urban environments that we don’t get to see from street level.

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Rooftopping view
Image: Tom Ryaboi
This photo makes it look like Ryaboi was suspended in mid air.

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We ask Ryaboi if he has a favorite rooftopping location. “Picking a favorite roof would be like picking a favorite son or daughter. I love them all,” he replies. “However, I recently had the opportunity to shoot from the newly completed Unicredit building in Milan, Italy. It had an 83-meter [272-foot] spire that had spectacular views of the whole city. The combination of old and modern architecture there makes the landscape really unique.”

Rooftopping view of city
Image: Tom Ryaboi
A more conventional city view, until you notice the climber on the right-hand side.

As far as future destinations go, Ryaboi says he would love to take photos from the top of the Freedom Tower in New York City. In the meantime, he’s traveling through Europe and Asia. “I’m gradually moving to more motion pictures (timelapse and video) and I’d like to pursue the subject of connectivity on this trip,” says Ryaboi.

We thank him for sharing his insights and awe-inspiring photography with us here.

Sources: 1, 2, 3

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