A practice known the world over, the origins of "jazz funerals" are as complex as they are varied. Filmed over twenty-two years, City of a Million Dreams explores race relations in American society by training a lens on the unique and resilient culture of New Orleans, as represented in their long-standing burial traditions.

In 2005, writer and vlogger Deb "Big Red" Cotton left Hollywood for New Orleans and became a chronicler of the city's parading club culture spawned by the legacy of 19th century "Funerals With Music". She discovered diffuse origins that arose out of the confluence of African, European, Native American, and Haitian traditions whose intersections were uniquely situated in New Orleans. While exploring her adopted culture, prolific clarinetist Dr. Michael White— renowned for playing the "the widow's wail" in sorrowful dirges— offers a crucial contemporary link to a long lineage of local jazz musicians and social clubs. When Hurricane Katrina hits, Dr. White loses everything in the catastrophic flooding. As he rebuilds, he becomes an everyman, embodying the spirit of resurrection that accompanies Funerals With Music, a means by which New Orleanians across generations have steeled themselves against despair.

As the film's funerals accumulate, their role as caravans of collective memory is revealed, shaping Cotton's epiphanies and White's exploration of an ancestor who played at the dawn of Jazz. New Orleans burial customs both persevere and evolve as people of different tongues and colors reach the city — survivors of natural disasters, political violence, and civil rights struggles. Despite the series of changes over the decades, City of a Million Dreams honors ancestral memory by highlighting Congo Square, an area where enslaved African people were allowed to speak their own languages and practice their cultural traditions, as the wellspring from which Funerals With Music sprang.

As the city's social pressures continue to compound, a violent turning point hits a Mother's Day parade, and Deb Cotton and Dr. White are thrown into a search for the city's soul. Based on Jason Berry's celebrated book of the same name, City of a Million Dreams offers a thoughtful and comprehensive examination on this enduring local tradition that refuses to yield or conform.