A Hole in the Head (1959)

Synopsis
Although the main character, Tony Manetta (Frank Sinatra), in this light comedy tends to tip the scales towards being unbelievably unrealistic, the story is pulled off because everyone else is convincing. Tony is a widower in need of a financial bailout for himself and his son, so he asks for help from his brother Mario (Edward G. Robinson), a wealthy New Yorker. Tony owns a small hotel in Miami Beach but his impractical ways have made it a losing proposition. After Mario and his wife (Thelma Ritter) arrive in Miami, thinking of taking custody of Tony's son, they suddenly decide to try to match Tony up with the widowed Mrs. Rogers -- maybe that will teach him some responsibility. This was one of the last movies directed by Frank Capra. ~ Eleanor Mannikka, All Movie Guide