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Within the next nine years, Benson's active role in the Boston artistic community led to his acceptance as a member of the "Ten." This elite group of plein-air painters included Childe Hassam, Edward Simmons, Willard Metcalf, J. Alden Weir, Robert Reid, Edmund Tarbell, Thomas Dewing, Joseph De Camp and John Twachtman, and provided Benson with a support group whose company he continued to enjoy and exhibit with for the rest of his career.
Aside from a mural commission for the Library of Congress, Benson's artistic output falls into two general categories. The first - and the area in which he is now most famous-are his outdoor compositions of single figures or groups. The best of these works were done from about 1900 on. These usually depicted his attractive, goldenhaired daughters in flowing white dresses, basking under brilliant sunlight and silhouetted against verdant, colorful landscapes, bright blue skies and fleecy clouds. These paintings show the artist's fascination with light and color and are much more spontaneous than his earlier works.
During this fertile period, Benson also painted portraits and still lifes. His portrait commissions were mostly of society figures, and in the mode of 18th-century aristocratic portraiture, many included women with children.
The second category reflects Benson's involvement in sporting subjects, especially duck shooting. The popularity these paintings brought him enabled him to give up his 25-year teaching career to paint full time until his death in 1951 at the age of 89.