Born in Waterbury, Connecticut, Riley received his BA in Visual Studies from Dartmouth in 1995, and his MFA from Yale in 1998. In 2004, Riley was awarded the American Academy of Arts and Letters Purchase Prize for the work Giant Steps, now in the collection of the Virginia Museum of Fine Arts. In 2007, he was awarded a Guggenheim Award. Riley has exhibited regularly since 2000 including solo shows at the Pageant Gallery in Philadelphia and the Karl Drerup Art Gallery in Plymouth, NH. In New York, Rileys work has been included in group exhibitions at Lori Bookstein Fine Art and Reeves Contemporary. Riley considers the source work for his drawings very important. The subjects include maps of star constellations, poetry, and improvisational music. His work asks the question can rationality, as represented by pattern or methodical process be empathetic; and can the visionary or intuitive be rational.