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Photographer Tom Ryaboi is one of the pioneers of rooftopping, whose advocates evade security guards, dogs, even urban falcons defending their nests.

TOM RYABOI/BARCROFT MEDIA/LANDOV

Tom Ryaboi was 23 when he first did it. One November weekend five years ago, he took advantage of a gate somebody had carelessly left open. With a camera strapped around his neck, he climbed 41 floors to the roof of a building still under construction near Spadina Avenue and Bremner Boulevard.

Mr. Ryaboi was struck by his view of the downtown core. "Seeing it in all its glory, all these buildings are right in front of you, face to face, rather than you looking up at them. It was really exhilarating."

Elated, he stayed about 40 minutes, taking pictures of Toronto from above. When it got dark, he went home and looked at his photos on his computer. They were unlike any he had taken.

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Excited to share the experience with his friends, he soon convinced other photographers to join him on escapades, not only to the rooftops of skyscrapers, but also the tops of idle cranes.

It's a trend that's taken off, not only in Toronto, where he estimates there are now about 20 photographers "rooftopping," but in cities such as Boston and Chicago as well. The term "rooftopping" was probably coined by the late Toronto author Jeff Chapman in his 2005 book Access All Areas: A User's Guide to the Art of Urban Exploration.

Mr. Ryaboi, now 28, and his posse have scaled more than 100 buildings. They go up in all seasons, dressed like office workers or construction crew in steel-toe boots, jeans and workshirts to fit in and gain easier access. Unsurprisingly, they have also been caught by security guards and ticketed for trespassing a few times.

But the risk – they eschew harnesses – and the $65 tickets are worth it, Mr. Ryaboi says.

"I'd rather ask for forgiveness than permission," he says.

"I wanted to bring people up there with me and show them the city like they had never seen it before."

With that goal in mind, Mr. Ryaboi recently released a time lapse video of four months of life in the city, as viewed from above, compressed into just over four minutes.

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Titled City Rising, it is set to the background music of German composer Hans Zimmer's Journey to the Line. The project was full of challenges posed by motion control gear, constantly changing light, and aperture flicker. It also took patience – once the camera is set up, there isn't much to do but wait for the right moment.

When you spend up to eight hours on rooftops waiting for the perfect shot, the experience of gazing at decades of development and technology can lead to introspection. "You start thinking about where we've been and where we are going. And then naturally, you start thinking about your own mortality," Mr. Ryaboi says.

"You get a real rush. It's almost like holding your breath under water. When you come out onto a roof for the first time [and] you see the city, it's like your first breath coming out [of the water]."

One of his favourite rooftopping experiences occurred this spring when a security guard on a routine walkabout stumbled upon Mr. Ryaboi and his friend. After Mr. Ryaboi explained what the pair were doing there, the guard asked him to later take a family portrait with his wife and two children to send to his mother in India.

Since the release of City Rising, Mr. Ryaboi, who is also a photo editor with Blog TO, a blog about current events and food trends in Toronto, has been asked by building managers to return to the same buildings he had sneaked into, to take pictures of the vista from their rooftops.

Being badass has its privileges.

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