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A native Chicagoan, Richardson was educated at the St. Louis School of Fine Arts and the Academie Julian in Paris. He taught at the Chicago Art Institute for seven years. He has been described as a slight-built, gray-eyed man whose work was heavily influenced by the Art Nouveau movement. From 1892 on, if not earlier, Richardson made his living as a newspaper illustrator, working for the Chicago Daily News; he produced many pictures of the famous Chicago World's Fair of 1893, the World's Columbian Exposition. His employers valued his work highly enough the send him back to Paris to cover another world's fair there in 1900. A collection of his work for the Daily News was published in 1899.
In 1903 Richardson moved to New York City to pursue book illustration. His first project was Zixi of Ix, which was published serially in St. Nicholas Magazine in 1904 and 1905 and in book form in the latter year. Richardson followed that initial work with more book-illustration jobs, including the works of Hans Christian Anderson, Aesop's Fables, Mother Goose, Pinocchio, and East of the Sun, West of the Moon, among many others. After his death in 1937, Richardson was memorialized with a posthumous volume that matched traditional tales, like "Three Billy Goats Gruff" and "The Bremen Town Musicians," with brightly-colored illustrations by the artist.