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. Here, 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.