This was Pat Boone's final film under his seven-year contract with 20th Century-Fox. The studio had signed Boone in 1957, hoping he'd replicate the box office success of Elvis Presley, but Boone's screen charisma, and his longevity as a box office draw, never equaled that of Elvis.
The title role was offered to Marilyn Monroe shortly before her death. She turned down the role because she "didn't think she would be convincing as a boy."
The original Broadway production of "Goodbye Charlie" by George Axelrod opened at the Lyceum Theater on December 16, 1959 and ran for 109 performances starring Lauren Bacall.