Tony (Frank Sinatra) is a wannabe big shot hotelier who’s constantly broke. And while the carefree widower may not have money, he is rich in the unconditional love of his adoring young son Ally (Eddie Hodges).

But when Tony asks his wealthy brother Mario (Edward G. Robinson) for a loan, Mario, who disapproves of Tony’s swinging lifestyle, agrees to help him on one condition: settle down or give him custody of Ally! He’d have to have a hole on the head to agree to Mario’s terms…wouldn’t he? (1959)