After a chance encounter, musician Craig decides take a substitute music teacher gig to win over his high-school sweetheart, Victoria. Things don't go exactly as planned with Victoria, but he connects with the students and colorful faculty. Inspired by Craig's real-life experiences as a music teacher.

Craig is disgusted with Ben's sloppiness and lack of a job. So, in hopes of lighting a fire under Ben to pull his weight, Craig invites Jimmy to move in and share Ben's room. Elsewhere, Principal Taylor is asked to watch Supervisor Dalton's dog, Mr. Pickles. But when Mr. Pickles runs away, Ashleigh and Samir must do some scientific detective work to help track him down and save Principal Taylor from Dalton's wrath.