To keep dry in the rain, Pickles puts a bucket on Milo's head and sends him off to school. Funzie, the cool guy, thinks Milo's bucket is hip, so the next day, everyone's wearing a bucket on their heads. Milo finds himself running with the in-crowd, so he sets out to launch a strange new line of apparel -- with disastrous results.

Milo runs for school president against Debbie Klimer, leader of the snobby Debbies, and he loses -- but then his opponent suffers a freak accident. The Klimer family fakes young Debbie's death while she goes under the plastic surgeon's knife, but the operation is less than successful and Debbie returns looking like The Phantom of the Opera. Shunned by her upscale family and friends, The Oblong clan and the valley kids take in the reject Debbie as one of their own. But when Debbie's cheerfulness starts getting on everyone's nerves, the valley kids turn to the freakish school nurse to get Debbie back with the in-crowd.