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The Four Eton Boys were educated in small towns near St. Louis, where they all gained dramatic experience in amateur productions. Charlie and Jack Day toured the country for nine years as acrobats, playing the Palace Theatre on Broadway nine times in a single year. In 1923 the introduction of their songs in their act was so successful that they were booked at every variety theatre on Broadway, appeared in the musical comedy Rufus Lemaire's Affairs, and were featured in a two-reel comedy film. After singing with the Four Rajahs and announcing at station KMOX, St. Louis, Art Gentry joined the quartet as lead. Earl Smith left vaudeville in the Middle West for New York night club work, joining the Day brothers at the Nut Club. A popular CBS feature, the Eton Boys enlivened Borden's Forty-Five Minutes in Hollywood and were heard in the Columbia Varieties program. They made Paramount and Warner shorts and toured the Loews Circuit. They recorded for Columbia records and in 1935, they joined the cast of the Socony Sketch Book, the weekly radio series conducted by Johnny Green.