The opening of My Summer Story makes direct reference to the events of A Christmas Story, and the ending narration strongly parallels that of the earlier film. However, the sequel features an entirely different cast, with two exceptions. Both movies feature Tedde Moore as Ralphie's teacher, Miss Shields, and Jean Shepherd as the narrator, the voice of the adult Ralphie. Charles Grodin stars in My Summer Story as the Old Man (Ralphie's father), Mary Steenburgen plays Ralphie's mother, and Kieran Culkin plays Ralphie.
My Summer Story has several plotlines, one each for Ralphie, his father and his mother, followed by one involving Ralphie and his dad on a fishing trip. Ralphie's quest for most of the movie is to find a top tough enough to knock a bully's top out of a chalk circle in a game of "Kill." The Old Man has a series of skirmishes with his hillbilly neighbors the Bumpuses. Ralphie's mom would like to finally get something other than a Ronald Colman gravy boat on dish night at the local cinema.