The plot takes place in December of 1963 when Frank Sinatra Jr. is a struggling lounge singer, deep in his father's shadow. A young wannabe stock tycoon Barry Keenan (Grant Gustin), with an ex-wife, alimony payments, a pill-addicted mother, and a similar monkey on his own back (the result of a car crash), comes up with a harebrained scheme to kidnap Junior and hold him for $240,000, ransom, chaos ensues. Barry succeeds in stealing Junior at gunpoint but after that, it's one badly improvised move after another, until Barry bungles his way into prison.