The minstrel show occupies a complex and controversial space in the history of American popular culture. While it is seen as a relic of America’s deeply shameful and racist past, it also provided the first vehicle by which African-Americans were able to enter the entertainment world. This book investigates the often ignored 20th century history of minstrelsy as it entered the age of mass media, addressing such minstrel stars as Al Jolson, Bing Crosby, and Mickey Rooney. Tracing the history of minstrelsy through to its abrupt end in the 1950s, this book is a chronicle of “modern” minstrelsy and America’s rapidly changing values.