Tired of trying to find the right scene in your area? Go up on the roof, where the challenges are many and the town’s at your feet. Two intrepid plein air painters in Philadelphia share their tips on how to tackle the difficulties in painting a vista from a rooftop.

Aaron Thompson painting on a rooftop in Philadelphia
Aaron Thompson painting on a rooftop in Philadelphia

Everyone loves the view from a tall building’s roof. One can see how the city is laid out, and one can look for landmarks and observe how the buildings, which look so different at ground level, interact with the vertical tableau of an urban scene. But the very thing that makes a rooftop view so interesting — its vastness and complexity — makes it a hard subject to paint. Artists must summon their best editing skills to make a strong composition out of the jumble of boxes and angles beyond.

“In the country there are gently rolling hills, and many soft and organic forms of trees and shrubs and the like,” says Michael Manley, a teacher, painter, master’s student at the Pennsylvania Academy of the Fine Arts, and an immensely successful comic book artist. “In the city things are much sharper and there are more angles and lots of details like windows, street lights, cars, trucks, shingles, and all sorts of wires and doodads. Things and objects are jutting at all angles. I think often because of this people will find it a lot more challenging in choosing what to paint.”

"Metropolitan Rooftop," by Aaron Thompson, 2013, oil

“Metropolitan Rooftop,” by Aaron Thompson, 2013, oil

Where do you start, and where do you stop, in terms of what to include in the composition? There may not be many wrong answers, but there are some strategies that are better for achieving a good design. Manley says it helps to pick the right building from which to paint. Next, you need to be careful about how you fill your compositional space. “I try to look for the unusual view, an exciting composition that gives all four corners of my painting something different,” says Manley. “The corners and the bottoms of our paintings can often be weak areas. I think of Diebenkorn’s Ocean Park paintings, or Hopper, or the simplicity of Sargent in his statement of clear domains of sun and shadow. A little can say a lot; you don’t need every window.”

Time is a greater enemy on the rooftop than it is in a pastoral setting, Manley argues. “Since the city terrain is mostly vertical forms, buildings and the multitude of cast shadows create a sense of dynamics as they cut through, up, over, down, across, or are cast onto other surfaces or planes,” says Manley. “However, any vertical form will act as a sundial, and as the sun moves the shadows will move like the shadows on a sundial. One of the biggest differences between the city plein air and the country landscape is that when the sun moves on a circular form, like that of a tree in a field, the light stays consistent and lasts longer on the sphere; the interior or core of the trees or shrubs stays pretty much the same until the sun is very low to the horizon. In the city, the light on a cube — which is the simplest way to think of buildings — will stay the same before or after solar noon, but depending on the plane’s angle to the sun, it can suddenly shift greatly. The fact is you never have enough time — it’s always a sprint — so really look for a while before you paint. Even jotting down notes can help later when conditions change.”

Another scene captured from rooftop
Another scene captured from rooftop

The sheer vastness of the scene can cause complications in your drawing. Although some of Manley’s fellow painters chose to focus on nearby objects and let the vistas behind them enhance the subject, painter Aaron Thompson tackled a 180-degree panorama. Each time he turned his head, he was seeing a different view with different perspective issues. Painting such a scene without careful thought can lead to distortion that would confuse, distract, or annoy the viewer. Luckily, Thompson is a thinker.

“The notion of linear perspective can be expanded when taking our anatomy into account,” says Thompson. “Our eyes, head, and body are in constant motion. Therefore, what we experience is not simply a case of linear perspective with a fixed vanishing point. Reality for us exists in multiple vanishing points. For the ‘Metropolitan Rooftop’ painting, I was exploring this theory. I was working with a view that consisted of 180 degrees. So, fixing my posture and feet at a single point, I was able to record where my head and eyes moved using multiple vanishing points. I worked on a 1:1 ratio, which is why the painting expanded to 11 1/2 feet. If you stand in front of the painting where I stood when painting it, there is a sweet spot where our eyes attempt to bring together the floating vanishing points. This was all in an attempt to re-create a more truthful representation of my experience.”

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