chosen painting

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What interested me immensely about Hopper's painting was this tormented man at the centre. There is a nude woman beside him and we are led to believe that whatever has occured between them is the focus of the man's thoughts. But I was more interested in the fact that he is clearly reflecting on something - 'philosophising,' as the title says. It seems that he is unhappy and has lost something, so I thought it would be interesting to extend this idea of reflection and loss.

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What is he reflecting on? What has he lost? Is it to do with the open window, the light and the world outside?

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Image source: Wells, Walter. Silent Theater: The Art of Edward Hopper. London: Phaidon Press Limited, 2007.