Fletcher Ransom was born and died within a few miles of Kalamazoo, Michigan, but in between, his art career centered in New York City and Joliet, Illinois, near Chicago. Most midwestern artists began their study at the Art Institute of Chicago. Ransom, being no exception, was there from 1892 to 1893, then went on to the Academy of Fine Arts in New York.

By 1898 he had begun his illustration career as a "special artist" for Collier's Weekly, for which he made images of soldiers embarking for Cuba in the Spanish American War. He went on to illustrate articles for Youth's Companion in 1897-98, Harper's Weekly (1898-99), McClure's (1899), and Saturday Evening Post (1900), among many other magazines. He also illustrated several books, including Jesse Williams's Adventures of a Freshman (1899), Marguerite Cunliffe-Owen's A Doffed Coronet (1902), Emily Wheaton's The Russells in Chicago (1902), Japan: Her Strength and Her Beauty (1904), and Richard Barry's Sandy from the Sierras (1906). Reportedly he illustrated several books authored by the political reformist David Graham Phillips, who was gunned down in 1911. On his own, Ransom authored and illustrated a book of satirical cartoons about Theodore Roosevelt titled, My Policies in Jungleland (1910).

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His later career was primarily devoted to painting calendar pictures. For seventeen years he produced calendar illustrations for the Osborn Company of New York. About 1915 he moved to Joliet, Illinois, where for eighteen years he made calendars for the Gerlach-Barklow Company. Between 1931 and 1944 he painted fourteen calendar pictures for the Illinois & Midland Railroad showing various scenes from the life of Abraham Lincoln (now in the collection of the Abraham Lincoln Presidential Library and Museum in Springfield, Illinois). He was also involved in the Public Works of Art Project for Illinois in 1933-34. In 1935 he moved to Plainwell, Michigan, where he later died.

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Source: Art at the Jonathan Club, Jonathan Art Foundation