Taylor was born in Carbondale, Illinois and attended Southern Illinois Universityfor one year, which now houses his papers. He graduated from University of Illinois at Urbana-Champaign with a Bachelor of Arts in 1933. After college, he became a journalist and won awards for reporting. In 1939, he became a writer for The New Yorker magazine as an author of biographical sketches. Additionally, his work appeared in The Saturday Evening Post and Reader's Digest.
From 1942 to 1946, Taylor served in the United States Navy during World War II. During his service, he wrote numerous stories and Adrift in a Boneyard as an extended fiction about survivors of a disaster. In 1949, The Saturday Evening Post commissioned a series of biographical sketches of W. C. Fields. He published them together as W. C. Fields: His Follies and Fortunes. He continued to write biographies, including one of Winston Churchill, as well as fiction.
Taylor's 1958 novel The Travels of Jaimie McPheeters, about a fourteen-year-old and his father in the California gold rush, won the Pulitzer Prize and was purchased for a film, but eventually became a television series instead. A Journey to Matecumbe was adapted as the Disney TV movie, Treasure of Matecumbe in 1976. His novel Professor Fodorski served as the basis for the 1962 musical All American. His semi-autobiographical 1964 novel Two Roads to Guadalupe also was successful.