Timmy finds his old toy rocket and imagines that he and Brushbrush are astronauts in space. They head to Planet Shmengee to liberate the space station from the Cavity Goon and Miss Sweety.

Timmy dreams that he and Brushbrush win a dream vacation to Molar Island. Timmy ends up helping the locals when the ancient crown of King Cuspid has been stolen by the Gingivitis Tribe and the island will sink if the ancient crown of King Cuspid is not returned to the hole it was placed over.

Timmy and his friends go to the beach, but there is just one problem: Timmy cannot swim, and neither can Waxie! Timmy then imagines himself as a lifeguard, and his friends are competing in a surfing competition against the notorious cheater Goon Doggy.

The Cavity Goon and Miss Sweety plot to capture Brushbrush in order to bait Timmy and hand him over to the Tooth Fairy.

Timmy gets a case of the itchy polka dots on the day of the Flossmore Valley Fair. It's up to Mr. Wisdom to read Timmy a medieval story about the origins of the childhood disease.

Young Sidney Cyclops wants nothing more than to be the greatest paperboy in the world. Unfortunately, he cannot see. It's up to Timmy, Brushbrush and Bubbles to help Sidney.

Timmy reads to his friends a western story, where Sheriff Timmy deals with outlaws Goony the Kid and Miss Sweety when they come to Big Mouth Gulch.

During a rainy day, Timmy imagines that he is Captain Good Guy, and Brushbrush is his first mate. They work to save Sunny the Sun from The Cavity Goon and Miss Sweety.