At the height of his fame, Jim Henson delivered two films that deviated from his renowned Muppets and Fraggle Rock franchises. The Dark Crystal (1982) and Labyrinth (1986) hint at where Henson could have taken puppetry had he lived longer. They represent the best of Henson’s fantasy world-building, beautifully crafted scenery, and, mastery of the puppet arts. More than thirty years later, revisiting these films produces two insights. The self-evident one is that they withstand the test of time; still heavy, haunting, and Homeric in the case of The Dark Crystal, while Labyrinth remains charged, comical, and campy. The lesser realized truth is that both films are hallmarks of a storytelling that sought to strike a balance between adult and child audiences, challenging adult notions about certain forms of entertainment.