A Hole in the Head (1959)

In the sun-drenched landscape of Miami, Tony Manetta, a charismatic widower, navigates the choppy waters of running an on-the-verge-of-bankruptcy hotel while simultaneously raising his grounded 12-year-old son, Ally. His life, a cocktail of failed payments and flamboyant entanglements with women, is further stirred by Shirl, an alluring flame who only stokes his irresponsible tendencies. Tony's financial desperation drives him to his pragmatic brother, Mario, a man living a life as structured as Tony's is chaotic. Mario, however, is not a well of unconditional assistance. He proposes a bailout, but it comes with non-negotiable conditions: Tony must either surrender custody of Ally or marry a "nice, quiet little woman" handpicked by Mario himself. Caught in a vise between his carefree lifestyle and the need to shield his business from downfall, Tony decides to play along with Mario's plan, all the while intending to dance to his own tune. His strategy seems foolproof until the woman Mario introduces turns out to be as captivating as Eleanor Parker, setting the stage for a whirlwind of unexpected emotions and decisions. Will Tony be able to pull himself out of this financial abyss without losing his son or his freedom? Or will he discover a new life in the arms of a woman he never expected to meet? The Miami heat isn't the only thing rising in this engaging tale of love, family, and the price of dreams.

A Hole in the Head is a comedy movie featuring Frank Sinatra.

It is possible to buy A Hole in the Head on Amazon Video, Apple TV and Vudu.