Starting a new Cityscape Painting

It has been a while since I painted a cityscape painting. I think the last one that I did (and was actually one of my first) was my Dolores Street painting in 2013.

I'm a big fan of artist Wayne Thiebaud, and am quite obviously influenced by him. I love all the different types of subject matter that he works on, but have always loved his Cityscapes. Many of his cityscapes are influenced by San Francisco, with his exaggerated compositions of steep streets.

This is a photo that I took on a training walk in San Francisco last year. It is Bradford Street, in the San Francisco neighborhood of Bernal Heights. At the time, it was the steepest street in San Francisco (it still may be, but that title seems to shift frequently). The training walk that day was full of very steep hills. When we were in Bernal Heights on top of one hill, Linda pointed across the hill that we would be climbing up next, and that was Bradford Street. I took this photo from the top of one hill, looking across to the next. I really like the perspective that was achieved, and knew immediately that I wanted to do a painting of it.


The Original photo of Bradford Street

There are several things that I like about this composition: I really like the perspective, in that the viewer is looking across at the hill, rather than up at it, or down it. I also like the red building at the bottom right, as I feel it anchors the composition. Most of the houses on the left side of the street were identical from the front facades, and are very boxy from the side. I also like that most of the houses are probably built in the 50s, so mid-century modern style, which is not what one typically thinks of for San Francisco architecture.

Anyhow, I finally got started on this cityscape painting today. I knew I wanted it to be large, so I primed a 48"x36" canvas. I love painting on large canvases. :)

I was pretty intimidated by the thought of how to start this one. I figured it might take me several house to just pencil in the rough outline of all of the buildings, and that I'd need to concentrate heavily on perspective and accuracy.

To my surprise, when I asked my instructor, Dean, for his suggestion on how to start, he suggested painting in the trees first! He suggested this so that I wouldn't be as intimidated by all the buildings and details. He also suggested that I paint monochromatically so that I wouldn't get caught up in color.

It really worked! The positioning of everything that I put in so far is by no means accurate, but it is very loose in style, and I really like that. I used only one color which I watered down with various amounts of medium. I was pleased that by the end of the session, the canvas was pretty well outlined and filled in.


early progress with just the trees


outlining some of the buildings and streets around the trees


Wallace worked very hard while I was painting (and did a very good job of blending in with Dean's couch.).


a photo that Dean took of me while I was painting this morning