When Timmy finds his old toy rocket, he imagines that he and Brushbrush are astronauts in space. Timmy and Brushbrush head to the planet shmangy to liberate a space station from the Cavity Goon and Miss Sweetie.
Timmy prepares for his birthday party as his friends prepare a surprise for him in secret. Upon visiting Mr. Wisdom, Timmy is shown what Flossmore Valley would be like if Timmy was not around.
Timmy dreams that he and Brushbrush are taken to 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 where his friends are competing in a surfing competition against Goon Doggy.
The Cavity Goon and Miss Sweety plan to get rid of Brushbrush and Timmy by capturing Brushbrush as bait so that they can capture Timmy and hand him over to the Tooth Fairy.
Timmy, Brushbrush, and Bubbles head to the desert and enter the Uncommon Pyramids where they help Mumfred the Mummy find his parents.
Timmy gets a case of the Itchy Polka Dots on the day of the Flossmore Valley Fair. In order to take care of Timmy, it's up to Mr. Wisdom to read to Timmy a medieval story on how the Itchy Polka Dots got started. The story involves Squire Timmy going out on a dangerous and perilous journey to beyond the Not-So-Sure-Its-A-Forest to grab some polka berries from the Polka Berry Bush to make King Louie of Floss-a-Lot get cured from the Itchy Polka Dots. During his quest, Squire Timmy has an encounter with Merlys the Magician, Bubbles Hood, the Gingivitis Gang, and the Polka Berry Bush guardians the Cavity Goon and Miss Sweetie along the way. Brushbrush gets the Itchy Polka Dots.
Sidney Cyclops cannot be the greatest paper boy in the world if he cannot see. So Timmy, Brushbrush, and Bubbles help Sidney to see in order for him to be the greatest paper boy in the world.
During a rainy day, Timmy imagines that he is Captain Good Guy, and Brushbrush is his first mate where they work to save Sunny the Sun from pirate versions of Cavity Goon and Miss Sweetie.
Timmy reads to his friends a western story, where Sheriff Timmy deals with outlaws Goony the Kid and Miss Sweetie when they come to Big Mouth Gulch.