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".