The film was a sequel to Tom Sawyer, which was financed from United Artists and Reader's Digest. Even before that film had been released, producer Arthur Jacobs arranged for finance for a sequel based on Huckleberry Finn. The director was J. Lee Thompson, with whom Jacobs had worked several times, most recently on two Planet of the Apes films.[1]
Paul Winfield said he would only agree to the movie if the producer and director would guarantee there would be no "singing slaves".[1] "Gone with the Wind was one of the traumas of my life," said Winfield.[2]
Like Tom Sawyer, the film was shot in Arrow Rock and Lupus, Missouri. It was also shot in Natchez, Mississippi. Filming started 18 June 1973.[3]
Filming had only just began when Arthur Jacobs died of a heart attack in Los Angeles. Robert Blumofe was assigned to take over time. Filming resumed after the break of one day. Natalie Trundy, Jacobs' wife, had a role in the film and had to fly back to Los Angeles then return to location.[4]
Paul Winfield was arrested for possession of marijuana in his hotel room. (He claimed he had been sent it in the mail and was framed.) Thompson said the treatment by Winfield of the local police was "abominable" and that "I would never encourage a company to come to Natchez again."[1] This comment upset the Natchez media who wrote articles critical of Thompson. Thompson retracted his comments about the town but maintained the police had shown prejudice towards Winfield.[5]
Director J. Lee Thompson had problems with the synchronized musical direction. The third major problem was the unfortunate timing of writer Robert B. Sherman's knee operation.
Roberta Flack sang "Freedom" but insisted on having a guitar backing to her recording. She later threatened to sue if the original cast album was released with a dominant orchestral backing, and so although the album was recorded and printed, it was never released.
Despite these setbacks, the film still achieved some success and some of the film's songs, including "Freedom", are still considered classics.