For five decades, no American filmmaker has been as prolific—or as paradoxical—as Woody Allen. _From Play It Again, Sam_ (1972) to _Midnight in Paris_ (2011) and _Blue Jasmine _(2013), Allen has produced an average of one film a year; yet in many of these movies Allen reveals a progressively skeptical attitude toward both the value of art and the cultural contributions of artists. In this second edition Peter J. Bailey extends his classic study to consider Allen's work during the twenty-first century. He illuminates how the director's decision to leave New York to shoot in European cities such as London, Paris, Rome, and Barcelona has affected his craft. He also explores Allen's shift toward younger actors and interprets the evolving critical reaction to his films—authoritatively demonstrating why the director's lifelong project of moviemaking remains endlessly deserving of careful attention.