The son of a harness maker and sadler, Anderson was the oldest of seven children, and brother of writer, Sherwood Anderson. He received his earliest art training, in crayon portraiture, in exchange for cleaning services to a local house painter in Clyde, Ohio, to which the family had moved in 1884. Anderson moved to Cleveland in 1891, where he worked at retouching faded photographs and executing crayon portraits, while attending evening art classes. By 1893, he was enrolled part-time in classes at the Art Institute, Chicago, under James Earle Fraser. In the antique class of John H. Vanderpoel, he became friends with fellow students, Joseph Christian Leyendecker and Frederick Frieseke. Anderson assumed Leyendecker's position at the engraving house of J.C. Mantz & Company in 1896, thus beginning his career as a commercial illustrator. In New York briefly in 1898, the artist worked for the Sunday edition of the Morning Telegram. By 1899, he had become resident artist of Woman's Home Companion in Springfield, Ohio.
Anderson went to Paris in 1900, enrolling at the Academies Julian and Colarossi, while also studying with Alphonse Mucha. In the summer of 190l, Anderson joined the painting classes conducted en plein air by American expatriate George Hitchcock in Egmond, Holland. In 1903, his work was exhibited in the Paris Salon. Anderson married Helen Edgerton Buell, a concert singer from Marietta, Ohio in 1904, before returning to America.
Settling in New York, Anderson continued to support himself through commercial art, drawing illustrations for novels and magazines including Scribner's, Collier's Weekly, Good Housekeeping, and The Saturday Evening Post.
From 1909 to 1912, the artist was again in Europe, traveling in Spain, Italy, and Holland; he also encountered Frederick Frieseke, who persuaded him to join the colony of artists surrounding Monet at Giverny in the summer of 1909. Along with Freiseke, American artists including Frederick MacMonnies, A. B. Frost, Lawson Parker, Theodore Butler and Edmund Greacon, also worked at Giverny in the first decades of the century.
With the recognition of his first major prize, the Second Class Medal in the Carnegie Institute Annual of 1910, for The Idlers: August, and the patronage of General Charles G. Dawes, diplomat and vice president of the United States, 1925-28, Anderson was able to abandon his career as an illustrator and support himself by painting. On his return to America in 1912, he established himself in Westport, Connecticut, where he remained until his death. Among residents of the artists' colony which subsequently developed there, Anderson became known as the "Dean of Westport Painters."
Along with conducting art classes in Connecticut, Anderson taught at the Academy School from 1931 into 1943, primarily as an instructor in the life class. He was a regular exhibitor in the Annuals from 1903, and received Altman prizes in the winter exhibition of 1917, and annual exhibition of 1926.
Sherwood Anderson described his brother's career as "primarily one of a patient, determined struggle; under adverse conditions, and of a determination that has never weakened." (Price, p. 133).
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