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Fitted with a plaster cast for his injured foot, Poopshkin is provided two crutches and prescribed a long period of rest. The crutches, two terrible troublemakers, help Poopshkin discover happiness during hardship. His boredom leads to several mischievous pranks that cause Lori and Juney to confront his bad behaviour, only to have Poopshkin claim, "the crutches did it."

Poopshkin's first Christmas, there is so much to learn if he wants to be like everyone else.

Poopshkin and Pepin are introduced to Bobber's new baby brother, Jerbear. Poopshkin discovers that little brothers are awful and then plans to make amends with his older sister Juney.

The story follows Poopshkin and his friends as they scale Santa Monica Mountain to save Halloween from a very scary evil Witch who has taken all of the candies except for one, a purple candy.

Poopshkin and his friends ambitiously attempt to make a movie adaptation of Hamlet. After their initial failure, they realize that each cast and crew member must adapt to a new role in order for their production to succeed.