The movie Cool Money is mainly focused around a clever and experienced thief by the name of Bobby Comfort. During his lengthy prison sentence, Bobby escapes and cleverly finds a way to get all of his charges dropped. Once his name had been cleared he returns to continue a life with his wife and child. However, Bobby has come to find that he is no longer satisfied with his ordinary family life. Despite his love and devotion to his family, he soon finds that his old life of crime is drawing him back in. Giving him the risk and adventure he has been longing for.