Born in Iowa, Bailey attended the School of Fine Arts at the University of Kansas. He would later earn both a Bachelors and a Masters in Fine Arts from the Yale University School of Art. Bailey has taught at Indiana University and at Yale University where he briefly served as Dean of the School of Art. Since 1979, he has served as the Kingman Brewster Professor of Art at the Yale University School of Art. He is best known for his paintings, prints and drawings of still life and the figure. Bailey's work is in the collection of the Art Institute of Chicago, the Hirshhorn Museum, the Museum of Modern Art in New York, the National Museum of American Art, Smithsonian Institution and the Whitney Museum. He is an elected member of the American Academy and Institute of Arts and Letters.