This painting was done in two different sessions at two different times. The man was painted from a live model in an art studio setting. I did it as a demonstration painting for an art class I was teaching. We started out with the model simply wearing a t-shirt and no hat. And then in subsequent sessions he added the suit, tie and fedora. So we actually dressed him up as we went along. It was a pretty interesting process. Anyway, at the end of the class, I simply painted a dark toned background which I never liked. I always felt that it needed a cityscape.

The finished painting I put away in my studio, figuring someday, I would revisit it. And then my son Gerry, who is an awesome upcoming artist, suggested we paint plein-air style together along the bend in the Chicago River. That setting was exactly what I wanted for this painting. I dug it out and brought the canvas with me to the city. I finished it in one sitting on a beautiful Sunday afternoon in June painting along side my son on the river. What a perfect day!