Big Brother helps Milton Chubb, a huge new cub, deal with the school bully and make friends with Bertha Broom, but then Milton and Bertha must meet in a match for a spot on the school's wrestling team.

Brother and Sister Bear don't realize the problems they will face when they agree to help Professor Actual Factual's super-smart nephew fit in at school.

Even though they are not into rad fashions, Brother Bear and Sister Bear join the other cubs' protest when Mr. Grizzmeyer enforces a strict dress code at Bear Country School.

Frustrated by their lack of artistic freedom on the staff of the school newspaper, Brother Bear and his friends start an underground paper and discover some basic truths about freedom of the press and responsibility.