Overview
A Hole in the Head (1959) is a DeLuxe Color American comedy film, shown in CinemaScope, directed by Frank Capra, featuring Frank Sinatra, Edward G. Robinson, Eleanor Parker, Keenan Wynn, Carolyn Jones, Thelma Ritter, Dub Taylor, Ruby Dandridge, Eddie Hodges, and Joi Lansing, and released by United Artists. It was based upon the play of the same name by Arnold Schulman.
The film introduced the song "High Hopes" by Sammy Cahn and Jimmy Van Heusen, a Sinatra standard used as a campaign song by John F. Kennedy during the presidential election the following year. Sinatra portrays a lowlife dreamer named Tony whose old friend Jerry Marks, now a rich man, expresses interest in his plan to build a Disneyland in Florida (the film predates Walt Disney World by 12 years)—until Jerry notices that Tony seems too desperate when the latter cheers for a dog upon which he's bet heavily. The movie ends with Tony, his lady friend Eloise, and his son Ally singing "High Hopes" on the beach. Sinatra sings "All My Tomorrows," another Cahn/Van Heusen song, under the opening titles.
Sammy Cahn and Jimmy Van Heusen won the Academy Award for Best Original Song for "High Hopes".
Plot
Tony Manetta moved from the shabby area of the Bronx, New York to Miami, Florida with two friends, searching for wealth and success. One friend became prosperous over the next 20 years (owning luxury hotels) and is a promoter, while his younger friend drives a local taxi. Tony manages a small hotel called Garden of Eden. He grew up poor but spoiled, spending money on expensive suits and a Cadillac despite always being in debt and refusing to become more responsible. He is also a widowed father of an 11-year-old son named Alvin (nicknamed Ally).
From Wikipedia (CC BY-SA 4.0).