Schestag studied philosophy, German, and Comparative Literature in Berlin, Paris, and Strasbourg. He received his doctorate at the University of Zurich in 1988 and his habilitation at the University of Frankfurt in 2003. He has taught at universities in Germany (including Bochum, Bonn, Frankfurt, and Munich), Japan, Hungary, and the U.S., including Johns Hopkins, Michigan, Northwestern, NYU, and Virginia. In the fall of 2013 he was the John P. Birkelund Fellow in the Humanities at the American Academy in Berlin. He joined the faculty of Brown's German Department in January 2014.