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Reginald "Cool" Coolidge is a struggling actor, fed up with taking stereotypical African American roles and waiting for his big break in a legitimate production. Until this time comes, he works at his mother's boyfriend's gas station to repay him for covering his college tuition. One day at the station, his ex-fiancé - and one true love - reappears at the pumps after 3 years of silence. Cool discovers that it is 36 hours until her wedding to a local lawyer. As Cool embarks on last-ditch attempts to win her back, he takes on the biggest "role" of his life while also learning the secret to mastering his craft.

A historical and present day look at the Wilmington Massacre of 1898 and how the descendants of the victims of the event are asking for legal action in regards to compensation.