Meet Tony (Sinatra), a wannabe big shot who's constantly broke. While the carefree widower may not have money, he is rich in one respect; he's got the unconditional love of his adoring young son Ally (Eddie Hodges).

However, when Tony asks his wealthy brother Mario (Robinson) for a loan, Mario who disapproves of Tony's lifestyle agrees to back his brother on one condition: settle down or give him custody of Ally! Tony may be desperate but he'd have to have a hole in the head to agree to Mario's terms, wouldn't he?