Sinatra plays a well-meaning gambler of a dad, Eleanor Parker is always great; good cast.
A Hole in the Head (1959) is a comedy film released by United Artists. It was directed by Frank Capra and featured Frank Sinatra, Edward G. Robinson, Eleanor Parker, Keenan Wynn, Carolyn Jones, Thelma Ritter, Dub Taylor and Joi Lansing. The film introduced the song "High Hopes", a Sinatra standard used as a John F. Kennedy campaign song during the presidential election the following year. Wynn plays a wealthy former friend of Sinatra's character who expresses interest in his plan to build a Disneyland in Florida (the film predates Disney World)—until he notices that Sinatra seems too desperate as he cheers for a dog upon which he'd bet heavily. The movie ends with Tony, Eloise and Alley singing "High Hopes" on the beach.
The screenplay was adapted by playwright Arnold Schulman, whose father was the operator of a Miami, Florida hotel. The protagonist of A Hole in the Head is a Miami hotel operator of The Garden of Eden. The actual hotel used for the exterior shots was the Cardozo Hotel...