Spike Lee's challenging film Bamboozled (2000) is often read as a surface level satire of blackface minstrelsy. Careful analysis, however, gives way to a complex and nuanced study of the history of black performance. This book analyzes the work of five men, minstrel performer Bert Williams, director Oscar Micheaux, writer Ralph Ellison, painter Michael Ray Charles, and director Spike Lee, all through the lens of this misunderstood film. Equal parts biography and cultural analysis, this book examines the intersections of these five artists and Bamboozled, and investigates their shared legacy of resistance against misrepresentation.