Editing Sweet and Lowdown (section)

=== Development ===
After his 1969 directing debut ''[[Take the Money and Run (film)|Take the Money and Run]]'', Allen signed a contract to direct a series of films with [[United Artists]]. Told to "write what you want to write," Allen, a clarinetist and avid jazz enthusiast, wrote ''The Jazz Baby'', a drama screenplay about a jazz musician set in the 1930s. Allen said later that the United Artists executives were "stunned&nbsp;... because they had expected a comedy. [They] were very worried and told me, 'We realize that we signed a contract with you and you can do anything you want. But we want to tell you that we really don't like this.'"{{sfn|Bjorkman|2005|p=36-37}} Allen went along with United Artists, writing and directing ''[[Bananas (film)|Bananas]]'' instead. In 1995, he dismissed ''The Jazz Baby'' as having been "probably too ambitious."{{sfn|Bjorkman|2005|p=36-37}}

In 1998, Allen returned to the project, rewriting the script and changing its name to ''Sweet and Lowdown''. Allen had originally planned to play Ray himself, but eventually cast [[Sean Penn]]. Allen also considered [[Johnny Depp]], but Depp was busy at the time.{{sfn|Bjorkman|2005|p=347-356}} Penn had a reputation for being difficult to work with, but Allen later said, "I had no problem with him whatsoever&nbsp;... He gave it his all and took direction and made contributions himself&nbsp;... a tremendous actor."{{sfn|Bjorkman|2005|p=347-356}}

Allen, in a retrospective, said that he told Samantha Morton to "play [her] part like [[Harpo Marx]]. And she said, 'Who is Harpo Marx?' and I realized how young she was. Then I told her about him [and] she went back and saw the films."{{sfn|Bjorkman|2005|p=347-356}}