Orson Welles was John Ford's original choice to play Frank Skeffington but Welles either lost or refused the part after intensely anti-Communist Ford friend Ward Bond publicly questioned Welles's loyalty to the U.S. Ford was furious at Bond. Welles and Ford were fans of each other's work.
Edwin O'Connor's 1956 novel "The Last Hurrah", on which the movie is based, is a fictionalized version of former Boston Mayor James Michael Curley, a celebrated rogue who raised municipal corruption to an art form.