Dr. Chinstrap was a psychiatrist who was an expert in the mental illness of hoarding. Wendy sought out his help to get Stan to deal with his own hoarding. In the course of his investigations, Chinstrap also discovered that Mr. Mackey was a hoarder, and attempted to hypnotize the two (along with a luckless shepherd) to regress to their childhoods to discover what caused their habit of hoarding. When Mackey's recollection proved so vivid as to suck Stan and the shepherd into his reality, Chinstrap sought the assistance the world's best dream infiltrator, Freddy Krueger, to help them.
Doctor Chinstrap has a full head of gray hair, gray eyebrows, and a gray mustache. He has a large, elongated head with large ears and has wrinkles on his face. He wears a brown suit with a white shirt, dark brown vest, and a dark blue tie.
- "Insheeption" - Hypnotized Stan and Mr. Yeoman to help them resolve their hording issue.
- "Reverse Cowgirl" - Appears on one of the bathroom screens sitting on the toilet.