As a young adult, Anderson held jobs as a house-painter, portrait photograph retoucher, and magazine illustrator. In 1893, he began studying at the Art Institute of Chicago.
Anderson traveled to Europe in 1900 to study in Paris and Holland. In 1903, his work was accepted into the prestigious Paris Salon.
Returning to the U.S. in 1904, the artist again worked as an illustrator, finding time to paint whenever he could. He returned to Europe in 1909, before permanently settling in Westport, CT in 1912.
Anderson was known for his depictions of women, painted with bright colors and fluid brushstrokes.