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-fiancée--and one true love--reappears at the pumps after three 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.