The film starts with Baker playing himself in a film that was planned, but never actually made, about his own life. Born to be Blue utilizes this film-in-a-film approach to draw out the glamorized, black-and-white version of Chet Baker with the so-called reality of the situation, even with the very unsavory issue of his womanizing and his own addiction to heroin. Also included is the love affair he would have with a struggling but ambitious actress named Jane, who is a composite fictional character, played by Carmen Ejogo, who also plays Baker's wife in the fictional film. He's out of prison, but still under the close supervision of his probation officer, who wants him to get a clean and steady job and get out of the lifestyle that has too many temptations for him at the ready, knowing that the methadone he is prescribed to kick the habit will only get him so far.