For 30 years, no American filmmaker has been as prolific - or as paradoxical - as Woody Allen. From Play it Again Sam (1972), to Sweet and Lowdown (1999), Allen has produced an average of one film a year. Yet with each new film, he reveals a progressively more sceptical attitude towards art. Merging criticism with biography, this work uses Allen’s ambivalent views of the artistic enterprise as the key to understanding his entire career. The author demonstrates how Allen’s films constitute a debate he is conducting with himself about the capacities of art to improve the quality of life and about the resulting price exacted upon artists and those around them. An underlying tension between reality and image is identified, demonstrating how the resolution of this conflict in each movie is revisited, critiqued, and reconfigured in the next.