Convinced his friends forgot his birthday, Timmy visits Mr. Wisdom and is shown what Flossmore Valley would be like if he wasn't around.

Timmy dreams that he and Brushbrush win a dream vacation to Molar Island, where they help the local tribe when the ancient crown of King Cuspid is stolen by the Gingivitis Tribe.

Timmy and his friends go to the beach, but there is just one problem: Timmy cannot swim, and neither can Waxie! Timmy 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, Brushbrush and Bubbles go to Egypt to undertake official pyramid investigation business exploring the pyramid of King Tooth Uncommon.

Timmy gets a case of the nasty, scratchy, 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.

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

During a rainy day, Timmy imagines that he is Captain Good Guy, and with First Mate Brushbrush, they set out to save Sunny the Sun from the Cavity Goon and Miss Sweety.

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.