The Artist's Road

The Artist's Road

Artists Painting Artists

Perspectives from The Artist's Road

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The Artist's Road
Jan 12, 2026
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Portrait of Willard Metcalf ca. 1921 Frank Weston Benson

Portrait of Willard Metcalf, ca. 1921, Frank Weston Benson

Just for fun (and we think each of these artists was also thinking that)—we put together a few favorite paintings of artists painted by their contemporaries—artists painting artists. Some of the portraits give us a little insight into the working conditions and equipment being used at the time—not so different from today, except of course, the long dresses and suit coats worn while painting. And it is fun to imagine Van Gogh and Gauguin painting each other as well as Matisse and Derain. Of course the cheapest model appears in artists’ self-portraits; the second cheapest is one’s painting companion!

Portrait of André Derain 1905 Henri Matisse

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