Michael Earl

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.

Wee Sing characters Punchinello, Sillywhim, Little Bunny Foo Foo, Weeber, Snoodle and Doodle, and Trunky (originally Tusky) who are all from earlier Wee Sing Videos, ride the Wee Sing Train to Singalingaland where Singaling (voiced by Mikey Moran) and Warbly (voiced by Maureen Robinson) are hosting a big musical party called "The Wee Sing Festival". Singalingaland also happens to be an extension of Tim and Annie’s game board, Wee Singdom. However, the main guest of honor (a singing rainbow) is missing, so as each character performs his or her respective performance, Chug-a-Long the engine and Cubby the caboose are sent to go look for her by asking a cirrus, stratus, cumulus cloud where she disappeared too. Eventually, she is found after Tim and Annie find her playing with their cat friend, Staccato, and as a reward, Chug-a-long and Cubby invited Annie and Tim and Staccato to attend the Wee Sing Festival, and Singing Rainbow is able to perform.

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 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.

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.

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.

Set in Flossmore Valley and Egypt, Timmy, Brushbrush and Bubbles visit the pyramids on their official pyramid investigation business as they explore the pyramid of King Tooth Uncommon.

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