The film, A Hole in the Head, was based on the Broadway play of the same name.[5] It debuted at the Plymouth Theatre on Broadway on February 28, 1957 and featured actor Paul Douglas in the lead role. The play earned a Tony Award for Boris Aronson in 1958 for Best Scenic Design. on July 13, 1957 the show closed for a total of 156 performances.[6][7] Frank Sinatra's agent, Bert Allenberg, bought the film rights for $200,000.

The film was released in 1959. 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.

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.