A Hole in The Head

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, Ruby Dandridge 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, located on Miami Beach's Ocean Drive. Shot over 40 days between 10 November 1958 and 9 January 1959, the film did not enjoy the smoothest of productions, especially during the location filming at Miami Beach. Sinatra's relations with the press were problematic, the media seizing on every anti-Sinatra rumor they could find.

Aided by William Daniels, Capra completed the film a full eighty days ahead of schedule, its final production cost of $1.89 million well under the allotted budget. The film opened on 17 June 1959. Although having some positive reviews, the film was only a modest box-office success, grossing $4 million in America.