The story of a blue octopus and his dog that looks like a hotdog, named Weenie, and their friends like Daisy the daisy, and Henry the penguin. They go on adventures in their town that usually involve a problem that needs to be solved.
Oswald and Weenie try to get ice cream from Johnny Snowman's ice cream truck but they miss it, so they walk all around town trying to catch up to the truck.
Oswald, Weenie, Henry and Daisy go camping in the park but it begins to rain so they rush back to Oswald's apartment and camp there instead.
Oswald tries to get rid of an unwanted umbrella on a warm sunny day.
Oswald gets caught in a wind storm while getting one more marshmallow for Henry.
After listening to Oswald play his piano Daisy wishes she could play an instrument so Oswald takes her to the music store where she tries out different instruments.
Oswald chases Weenie's run-a-way ball of yarn through Big City.
Henry has a feather sticking out on top of his head but is scared to go to the barber since he's never had a haircut before.
Oswald buys a pet fish that he names Flippy because of the flip that she does, jumping out of her bowl and splashing back in it.
Oswald goes to the dump to get rid of extra stuff. Along the way he gives it all away to other people and finds more stuff he wants at the dump.
Oswald and Weenie make a birdhouse together with suggestions from friends.
Oswald learns to roller-skate.
It is Henry's birthday, and Oswald tries to teach Henry to try new things on this special day. However, this almost means that Oswald's favorite television show ended with the message - May your day be filled with surprises.
Oswald and Weenie have a sleep over at Henry's apartment.
Oswald and Weenie's banana seed produces a much bigger fruit than they expected.
Oswald is separated from Weenie when a drip coming from the kitchen sink eventually causes a city wide flood.
Oswald is in charge of baking a cake for Catrina's birthday party.
Daisy collects leaves and Henry collects spoons so Oswald wants to collect something too so he tries to collect clouds.
Oswald meets a friendly dragon named Pongo, who wants to help, but only makes things worse.
Oswald, Henry, and Weenie set out to have a picnic and are soon joined by many of their friends.
Oswald hears music and thinks that a big parade is headed his way so he convinces Henry and Daisy to go with him to watch the big parade.
Oswald and his friends compete in a go-kart race.
Henry tries to rake the leaves but Oswald and Weenie keeps jumping on them which made him frustrated.
Oswald and the gang go to the beach.
Oswald is the judge of the Annual Big City Sand Sculpture Contest.
Henry believes that he can fly.
Oswald and Daisy find a duckling who has lost her mother.
Oswald schedules two events at the same time.
Oswald is excited to meet Henry's cousin, Louie. But the two penguins have a great time all by themselves. Oswald feels left out, but once Henry and Louie catch up on old times, they seek Oswald out.
After Henry decides to move back to the frozen north with his cousin, the others prepare a going away party for him. In the end, Henry decides to stay in Big City after saving them from being blown away.
Oswald's piano is broken, and he takes it to Maestro Bingo to get it fixed.
Oswald goes out into Big City to get some cocoa and a newspaper for Henry, who has a bad case of the Arctic Sniffles. But a rain cloud chases Oswald and Weenie until a rainstorm makes Oswald catch a cold.
Daisy accidentally breaks Henry's special vase. Oswald, Weenie and Daisy try to fix it in time before Henry gets back from his fly catching trip.
Oswald and Daisy make honey buns, but Daisy adds too much sticky honey, and they get stuck to each other, along with other friends and eventually it starts to rain and the friends got unstuck.
Oswald takes Catrina to pick some tutti frutti berries.
Johnny is sick, so Oswald and Weenie go to make a special ice cream delivery.
Pongo wants to become friends with Laverne the elephant.
Catrina flies away on a balloon and Oswald must save the day.
During a heat wave, Oswald, Weenie, Henry and Daisy go on a trip to find the sweetest snow.
Oswald finds himself stuck in the middle of a feud between Henry and Daisy.
Tickets are sold out for Sammy Starfish's concert and Oswald must find a way to see the show.
Oswald eats his last tomato for breakfast, he decides to get more by planting tomatoes in the garden, Oswald was surprised and upset when he saw one of the tomatoes have been half eaten, he discovered the tomatoes were eaten by an entire group of snails but ends up making a restaurant for the snails.
Oswald finds a giant bird.
It's the grand pet show, but Weenie is behaving peculiarly of Steve's woodpecker, Woodrow pecking down the tent.
Oswald, Weenie, Henry and Daisy go fishing but Henry whom is not catching a fish.
Oswald pet-sits for Roderick Robot's pet cat, Tinsel but Tinsel runs away and make things worse and makes Oswald frustrated.
Oswald tries to find an egg's owner.
Oswald babysits Catrina on a snowy day.
Oswald hopes for snow to fall on the day of Big City's snow festival.
Oswald finds a firefly.
The clock in the Big City's bells somehow was not working and Big City was still asleep, it was up to Oswald, Weenie, Henry and Daisy to figure out what was causing this stroking catastrophe to make the clock work again to wake up Big City.
Weenie disappears during a game of hide and seek.
Weenie gets clean before having her picture taken.
