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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. While working his day job, his ex-fiancée--and one true love--reappears after three years of silence. Discovering that it's only 36 hours until her wedding to a local lawyer, Cool embarks on last-ditch attempts to win her back. In the process, he takes on the biggest "role" of his life, while also learning the secret to mastering his craft.