John J. Baggs Jr. a sailor, who is a Vietnam veteran, checks into the Seattle Naval base's medical facility for minor treatment requiring tests. The testing results delay keep him from rejoining his ship when it sails. After he gets a clean bill of health, he finds out that he is unable to get paid or receive new orders because the U.S. Navy has lost his records. While they continue to search for his lost records, he can come and go from the base until the midnight curfew with a "Cinderella Liberty" pass issued by the medical facility. On his first night in a bar, he is racing the clock to find a woman, and spots Maggie, an attractive woman hustling sailors at a pool table. He challenges her at pool, and develops an interest in the woman, who turns out to be a prostitute living in a tenement with her bi-racial 10-year-old son Doug. Baggs runs into Doug who is out drinking beer, and begins spending time with him. He also develops a relationship with Maggie while going on outings with Doug, who is often left to fend for himself. Baggs attempts to create a normal life for her, and he succeeds for a while, but he has no status with the Navy, and has no pay and no benefits. Doug, suspicious and cynical at first, bonds with Baggs, who devotes his free time to the kid and even gets his teeth fixed at the naval base by an unqualified dental assistant. Maggie is pregnant by someone she met before Baggs; she gives birth prematurely, and the baby dies soon after birth. Distraught, Maggie needs to get out and distract herself, and returns to her former lifestyle. Finally, the Navy locates Baggs's records, and he is re-assigned. When he goes to inform Maggie, he finds she has abandoned Doug and left a note for Baggs telling him that he can keep Doug and that she is going back to New Orleans. In a subplot, Baggs is searching for a sailor named Forshay, who is in charge of training recruits and has his own tough approach to new recruits, including Baggs. After a brief fight, the two become friends based on their shared love of their Navy careers that override everything else in their lives. Forshay is demoted and is being discharged over his mistreatment of recruits, one of whom who had political connections. Forshay loses his pension, and Baggs finds him doing a menial job as a barker at a strip show. In order to stay with Doug, Baggs gets Forshay to change places with him and ship out under his name. Baggs and Doug then head for New Orleans to look for Maggie.
Cinderella Liberty received a nomination for a Golden Globe Award for Best Motion Picture. In lamenting many of the film choices he made in the years immediately following his Oscar and Golden Globe nominated performance in The Godfather, Caan mentioned Cinderella Liberty as one of the exceptions to those regrets, commenting that he liked the film a lot. The film is recognized by American Film Institute in these lists:
