No one represents the Italian American journey from undesirable outsiders to embraced citizens better than Frank Sinatra. From impoverished beginnings in an immigrant, single-parent household to world renown as "Chairman of the Board," he beat the odds to become one of the most influential and best-loved artists of the twentieth century. Sinatra's symbolic role to the millions of Italian American immigrants who looked up to him as proof of the American dream was far-reaching. From teenage crooner to civil rights activist to Reagan Republican, his shifting identity resonated deeply in Italian American culture. Now, a gathering of distinguished historians, journalists and critics explore Sinatra's impact on American culture, from questions of politics and civil rights to Italian mothering, morality, and ethnic stereotyping. These insights place Sinatra at the fulcrum of many controversial and timely issues that lend his influence a new depth and power, not only musically but in a broad historical context.