Different issues challenged the screen adaptation of Finian’s Rainbow, which was one of the most successful Broadway musicals of the 1940s but took more than twenty years to be released as a film. Using archival research, this chapter reveals the frustrated early attempts to make Finian’s into an animated film musical, partly blighted by the blacklisting of lyricist E. Y. Harburg in 1951. Ex-Disney animator John Hubley was hired to work on the film and created more than 400 storyboard sketches, designs, and character drafts for the movie. By 1954, ten key songs had been recorded by leading artists such as Frank Sinatra, Ella Fitzgerald, and Louis Armstrong; indeed, in an attempt to make the project as commercial as possible, Sinatra was assigned a part in nearly all the songs. A new prologue was added and changes were made to the story to soften its vigorous political message, but for a mixture of political and financial reasons the production was abruptly closed down; Finian’s Rainbow would not reach the screen until late the following decade.