A Hole in the Head is a 1959 DeLuxe Color CinemaScope American comedy film directed by Frank Capra and starring Frank Sinatra, Edward G. Robinson, Eleanor Parker, Keenan Wynn, Carolyn Jones and Thelma Ritter and released by United Artists. It was based upon the play of the same name by Arnold Schulman.

The film introduced the Academy Award-winning 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 sings "All My Tomorrows," another Cahn/Van Heusen song, under the opening titles.