Ollie Hopnoodle's Haven of Bliss (1988) - sequel to A Christmas Story
This was the first sequel to A Christmas Story, with all the same characters. Even a VHS is extremely hard to find. I remember this from The Disney Channel, 20 years ago. (below image is from a boot, disregard the DVD logo)
It's summertime in Holman, Indiana, and 14-year-old Ralph Parker can't wait to get his first job. His friends Schwartz and Flick are less enthusiastic, and the job turns into a nightmare presided over by the story's author, Jean Shepherd, in hilariously unconvincing movie makeup. Ralph's dad hardly can wait for the family's upcoming fishing vacation in Michigan at the movie title's resort but will have to drive their old car through a sea of troubles to get there. Fuzzhead the dog runs away and joins a wealthy family, to the consternation of Mom, who patiently handles über-whiner little-brother Randy and buys a whirligig as consolation.
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Tennessee Tuxedo and his Tales: The Complete Collection
Tennessee, a wise-cracking penguin, and his dimwitted pal Chumley resided in the Megalopolis Zoo, where they were constantly scheming against zookeeper Stanley Livingston and his assistant Flunky in an attempt to raise the quality of zoo life.