In Asa's fantasies, he's a singer-dancer extraordinaire bearing much resemblance to the late, great Frank Sinatra. Reality, however, tells a different story. With few actual career prospects, Asa (Jason Priestly) is a thirtysomething-year-old divorcé battling for visitation rights to his son. Asa's preoccupation with the glitz and glamour of the 1940s does little to help his relationship with his ex, who considers him to be a slacker, and therefore, an unsuitable father. Just when it seems like he may have to give up his dreams of grandeur for good, Asa is offered an advertising job by his uncle Billy. The world of advertising proves to be a welcoming place where Asa's love for the past is not only accepted, but actually encouraged. But if Asa wants to prove that he's a worthy father, he'll have to remove his head from the clouds, and rely on something other than his vintage charm.