Baloo and Kit are on their way to Walla-Walla-Bing-Bang to deliver an overloaded cargo of snow globe souvenirs. As they fly across the evening skies they are suddenly surprised by a small sea plane, nearly making them crash into the sea. Baloo recognizes the pilot to be Airplane Jane (although she rather be referred to as Aeroplane Jane), a female pilot Baloo once knew. He tells Kit that she has an annoying habit of making fun of him and always trying to prove she’s better than him. Before flying away to Walla-Walla-Bing-Bang, Jane tells Baloo she’s on her way to a mission for her friend Princess Grace. When he hears that she is offering a big reward for her service, it gives Baloo an idea on how to get even with Jane.
Both planes arrive at Walla-Walla-Bing-Bang. Jane is the first to arrive and after Baloo and Kit make their landing they follow her to the palace and spy on her and the Princess. Listening in on the conversation, Princess Grace explains to Jane that her long lost cousin Prince Rudolf (second in line to the throne) has returned to Walla-Walla-Bing-Bang and now challenges her right the throne. Her only chance to prove to be the rightful ruler should introduce the long lost Ruby Wings. Rudolf stole the map to the location of the treasure and keeps it safe in the reading room. Grace promises that whoever brings the Ruby Wings to her shall be rewarded with ten thousand Walla-Walla-Bing-Bang Woobles.
After listening in on the conversation, Baloo and Kit head down to Prince Rudolf’s costume party where they plan to sneak in with the guests and find the map. Kit attempts to get into a suit of armor but gets trapped inside while Baloo dresses up like a king wearing a broken flower pot for a crown, a dirty old sheet for a cape and a fly swatter for a mask. During the party, Baloo follows Jane to the reading. They both find the map inside a bookshelf on opposite sides. The two pilots try to both take it but end up tearing the map into two pieces. Prince Rudolf is on to them and sends two of his guards dressed as a horse to find them. They find Jane and Baloo and hold them at gunpoint until Baloo causes a line of books on the shelf to knock over and fall on the guards knocking them out. Baloo and Jane make a run for the docks with Prince Rudolf and his guards in pursuit. They board the Sea Duck and fly away, leaving behind Kit, who is still trapped in the suit of armor.
Baloo and Jane reach the Walla-Walla-Bing-Bang Rockies and as soon as they land they find the entrance to the hidden caves. It becomes a race for who gets to the Ruby Wings first and Baloo and Jane come across many of the cave’s hidden traps, nets, bottomless pits, arrows and rolling boulders. The pilots make it to a room where they have to pull a chain. The two pilots each try to pull it by themselves but it is clear to them that they need to pull it together. Together they successfully open the door to the treasure chamber where the Ruby Wings are kept. Unfortunately they discover they have been followed by Prince Rudolf and his guards but Baloo manages to seal the door before they can come in. Baloo removes places the wings on Jane and sends her out the window and glides back to the Sea Duck while he stays behind. Using a jack hammer, Rudolf gets through the door and reveals to Baloo that he’s not Princess Grace’s long lost cousin, but a fraud who plans to use the throne to steal a whole kingdom. After he finds out the Ruby Wings are gone, he has his guards throw Baloo out the window only to be rescued by Jane piloting the Sea Duck. Just as they are about to fly back to Walla-Walla-Bing-Bang, they are attacked by an armored blimp. Jane and Baloo fly above the blimp and using the Sea Duck’s anchor, they tear a hole in the front balloon, causing the blimp to crash. Jane and Baloo head for the way out, but due to a rock slide they won’t be able to climb it, since their starboard engine was damaged in the attack and overloaded. So Baloo lightens the load by throwing the souvenirs overboard just in time for them to fly out of the Rockies and back to Walla-Walla-Bing-Bang.
The next day, Grace is now crowned queen and wearing the Ruby Wings. She rewards Jane with the ten thousand woobles and rewards Baloo with a bill for the loss of the souvenirs. When he sees the payment reads ten thousand, Baloo knows for sure he’s going to be in deep trouble with Rebecca but Jane covers it for him by giving back the reward. She admits he was pretty good out there and couldn't have found the Ruby Wings without him. Suddenly, Kit manages to finally get out of the suit of armor, ending the episode asking Baloo and Jane, “Is the party over?”
- Ed Gilbert as Baloo
- R.J. Williams as Kit Cloudkicker
- Susan Silo as Airplane Jane
- Victoria Carroll as Princess Grace
- Dan Castellaneta as Prince Rudolf
Home video releases
- TaleSpin: Volume 2
- The title is a reference to the Indiana Jones film Raiders of the Lost Ark.
- The scene where Baloo and Jane run away from rolling boulders is also a reference to a scene from Raiders of the Lost Ark.