How others will see it. This film's all Sinatra, but he only has one and a half songs, during the opening credits and, much later, a half-hearted duet with his eager beaver Eddie Hodges. The other actors have perfunctory characters, except for Keenan Wynn and Carolyn Jones, who camp it up a bit, and Thelma Ritter, who oozes compassion instead of her usual no-nonsense humor.
The editing leaves something to be desired, since it is obvious that the actors are cropped over Miami Beach backdrops. Most viewers will see most plot twists a mile away, although they may wonder whether Jones or Parker will end up with Sinatra, since both women are sympathetically presented. Jones solves the problem for Sinatra by leaving him.
How I felt about it. The central question of A Hole in the Head is, is Frank Sinatra a bum? Technically, he is. He asks for handouts, he doesn't pay his employees, and in the end, he's unemployed. Like Vivien Leigh in A Streetcar Named Desire, he depends upon "the kindness of strangers," in particular, Eleanor Parker, as unlikely an eligible widow as only Hollywood could provide.
Can Sinatra change? All his machinations are geared toward preserving the status quo: running a third-rate hotel, and dating a high-maintenance woman who wants him to ditch his son. Only in the final reel does he try to change, refusing money from his big-shot former pal, refusing a check from his older brother, telling his son to leave for New York with his elderly step-parents. Steps toward true bum-dom are averted only by the film's requirement of a happy ending, however bogus. In real life, Sinatra would lose everything, and end up as a cab driver again.
It is easy to see why Hodges wants to continue hanging with Sinatra rather than live with the humorless Robinson. Sinatra reserves quality time for Hodges, and Hodges has his run of the hotel and it's eccentric characters. Robinson, who is old enough to be Sinatra's father, wouldn't let the kid have any fun. The presence of the child also makes it more plausible that lovely Parker would settle for unreliable, bankrupt Sinatra, since his adorable tot is part of the bargain.
The film has two curious characteristics. Spirited hottie Jones has a generous and endearing role as Sinatra's spoiled girlfriend. Yet she is unpleasantly squeezed out of the story, and one can imagine the director worrying about how to reconcile her departure with Parker's arrival.
The other odd development has Sinatra refusing money from both Robinson and old pal Keenan Wynn. As a practical man of the world, he would take the money. Briefly swallowing pride is better than the alternative, refusing all help and becoming a street person. Sinatra refuses the money only because we are supposed to want him to, which hardly makes his act genuine.