Harlem, New York, 1929. Kenneth Barker was an African American businessman, working a high position for a clothing company. Unfortunately for him, when the stock market crashed, so did his benefits, and his company was put out of business. This caused him to look for work elsewhere, which led him to the Cotton Club, a legendary nightspot in the Harlem district of New York City that for years featured prominent black entertainers who performed for white audiences. There he met Josephine Bailey, a twenty-five year old flapper, who worked as a dancer at the club. She was the only black woman who worked a dancer, despite the club being full of black entertainers. She was able to grant him a job, but she soon lost her own, due to racial conflict within her group. Kenneth did as well, due to guilt by association. The two began to skip town, looking for work and getting in all kinds of trouble. Each town they visited brought a new opportunity, as well as a new challenge. Will the two of them be able to overcome this Great Depression and flourish in America? Or will they find no luck, and be left to survive off of nothing but their love for each other and jazz music?