"My Summer Story" was intended to be the film's original title before MGM, presumably fearing unfair comparisons to A Christmas Story (1983), retitled it to disassociate it from its predecessor. By the time the film reached video, it reverted back to its former title.
Plans for a sequel to A Christmas Story (1983) began as early as December 1984. As such, the original cast was set to reprise their roles. When the film was finally made nearly eleven years later, the only cast member retained from the first film was Tedde Moore, who plays Miss Shields (that is, outside of Jean Shepherd narrating as an adult Ralphie).
The Parker brothers, Ralphie and Randy, are played by real-life brothers Kieran Culkin and Christian Culkin.
Jean Shepard's last film before he passed away in 1999.
This is the second film where the late Charles Grodin and Mary Steenburgen appeared together. The first was Clifford (1994).