What causes rainstorms? Rupert and Bill discover the shocking secret when an unusually strong storm strikes Nutwood: flying ships that sail the clouds through the sky around the world. Unfortunately, the Four Winds responsible for transporting the cloud ships suddenly disappear when Captain Peebles' monsoon is stopped over Nutwood. A quick investigation reveals they've been captured by the cloud pirate Captain Stubbs. To save the world, their home, and Captain Peebles, the boys will first have to save the Four Winds.
First appearance of the Clerk of the Weather.
This episode provides examples of:
- Accidental Truth: When Rupert asks his dad if he can keep a flying, sapient, baby cloud, his dad awkwardly suggests the cloud must want to go home. Dewey confirms he's right.
- Big Storm Episode: Because the storm was held up on its journey.
- Blow You Away: What power would you expect the Four Winds to have?
- Chekhov's Gun: The Professor's rainmaking potion.
- Death Glare: The way all the Four Winds look at Stubbs in every scene.
- Determinator: Peebles knows he doesn't stand a chance against Stubbs with the Four Winds, but he vows to "go down fighting."
- Do Not Touch the Funnel Cloud: Rupert reaches towards the funnel cloud for Bill, but by staying just beyond its edge, he never gets sucked in.
- Early-Installment Weirdness: Bill sings just fine in this episode, with Captain Stubbs even admiring his voice. The Running Gag of his terrible singing voice will be used every single time hereafter.
- Flying on a Cloud: Dewey provides this service for the boys.
- Forced into Evil: The Four Winds by Stubbs.
- Genre Savvy: Bill's used to Rupert's routine by now. As soon as the Clerk of the Weather says he needs to figure out what's happened to the Four Winds at the Valley of Storms, Rupert grins at Bill, who says, "Don't tell me — we'd be delighted to go to the Valley of Storms..." When Rupert insists they need to rescue the Four Winds from Captain Stubbs, his reluctant partner helplessly groans, "I knew you were going to say that!"
- Giver of Lame Names: Bill first suggests the name Fluffy for their new cloud friend. Said cloud is NOT having it.
- Gone Horribly Right: Bill tries to distract the East and West Winds from attacking Rupert. He succeeds... and brings them after him.Bill: Oops... that worked a bit too well...
- I Have Your Family: Stubbs controls the Four Winds by never releasing all of them at once and threatening the rest of their siblings if they don’t obey him.
- Journey to the Sky: The Episode
- Kidnapped by the Call/An Ally: Dewey whisks Rupert and Bill into the sky to help Captain Peebles with no explanation (well, as a cloud he can't really explain...).
- Lightning Gun: Stubbs' and Peebles' cannons and Stubbs' sword shoot lightning bolts.
- Literal Metaphor: Comes up twice.Bill: I've heard of being on Cloud Nine, but this is ridiculous!
- Later, after the contents of Stubbs' ship fall into Nutwood:
Mrs. Bear: I've heard of it raining cats and dogs, but this is ridiculous. - Making a Splash: How else would you expect a cloud to attack?
- Meaningful Name: Rupert names his new cloud friend Dewey.
- Mr. Exposition: Captain Peebles, the Clerk of the Weather, and Wendell each explain part of what's going on.
- Non-Indicative Title: Barely — there's only one cloud pirate (the other is just a sailor not interested in pirating anything).
- Not Quite Flight: The cloud ships easily defy the laws of gravity, but they can't move on their own without propulsion from the wind in their sails.
- The Old North Wind: The most powerful of the Four Winds.
- Painful Rhyme: Captain Stubbs resorts to this (or forces Bill to) several times. They usually involve adding an 's' to a word that doesn't need it because the word it otherwise almost rhymes with ended with an 's.'
- Rhymes on a Dime: Stubbs randomly starts speaking in rhyme whenever he feels like it.
- Shock and Awe: Stubbs himself doesn’t seem to have any supernatural powers, but all of his weapons are lightning-themed. Dewey can also generate a tiny lightning bolt.
- Silence Is Golden: The Four Winds never speak, but the looks they give Stubbs are worth a thousand words.
- The Sky Is an Ocean: And clouds are the cargo of flying ships.
- The Smurfette Principle: Only the South Wind is anthropomorphized as female.
- Solid Clouds: Dewey can carry the boys like a flying carpet.
- The Speechless: Dewey, being a cloud, can't speak but finds ways to communicate like turning into shapes.
- This Is No Time to Panic:Rupert: There's no need to panic, Bill... well, not yet, anyway...
- The Voiceless: The Four Winds never speak despite having human faces and mouths.
