It is 1927 and Josey is an African American teenager living in the rural Deep South. Unfortunately Josey is unhappy, unsatisfied, and desperate to make her life whole. Finally with encouragement from her friends Deek and Martha, Josey decides she is deserving of happiness, ignores her grandmother's wishes for her to become a teacher, and embarks on a journey to the North where she hopes to fulfill her dream of becoming a singer.

After Josey hops a train and arrives in Harlem, she meets up with Martha and Deek who help her find a place to live and introduce her to the Harlem nightlife. But in the midst of Prohibition and rampant racism, Josey soon realizes that her dream may be more difficult to attain than she imagined. It is only after she sneaks into an underground club and takes the stage that everything begins to transform for Josey.

Josey's Jazz shares the tale of an African American teenager who sets out on a quest to follow her heart and pursue her dream of becoming a jazz singer in 1920s Harlem.