The film was originally proposed in 1976 with Steve McQueen and Diana Ross in the leads, but negotiations fell through as McQueen refused to be billed second to Ross.[3] It was proposed again in 1979, starring Ryan O'Neal and Ross again in the leads. The project fell through due to irreconcilable differences in the relationship of the two stars. Costner stated that he based Frank Farmer on Steve McQueen; even cutting his hair like McQueen.

Madonna was considered for the role of Rachel. The deal was called off informally during an incident captured in her documentary Truth or Dare. This took place during the scene where Madonna met with Costner backstage; he congratulated her concert, calling her show neat, Madonna made fun of his "neat" remark after he left. Costner undoubtedly saw this after the documentary's release.

During recording of the song "I Will Always Love You", there were some different ideas for the cover version of the song until Costner and Houston decided the intro should be done a capella, having Houston sing with no music. That version would be the one used in the film.