"Handle with Caribbean" is the second segment from the 36th episode of The Lion King's Timon & Pumbaa.
Pumbaa, with Timon atop of him, starts swimming until they see a raft, which they hop on. Then, a meteor goes through the sail and Timon and Pumbaa hop on a cruise ship. Then the cruise ship hits an iceberg and Pumbaa, with Timon on his back, is swimming on a life ring.
Timon and Pumbaa get on another ship and see that there is nothing wrong with it, but little do they know, they're on a pirate ship. While Timon and Pumbaa search for the crew of the ship, three dimwitted pirates show up and state that they heard someone knocking. They therefore search for who it was that knocked.
The pirates find Timon and Pumbaa and capture them, but then Timon stops them and pretends to be their captain, calling himself "Captain Courageous." The pirates introduce themselves as "The Purplest Stupidest Pirates." Timon tells the pirates to take them to Nashville.
The pirates, however, misinterpret the word Nashville as they go to a resort with a man stating that his name is Nash and that is his villa. Timon tells the Pirates that Nashville is in America, but the pirates go to South America. Timon then tells them that Nashville is in North America, but the pirates go to the North Pole.
Timon draws an X on a map to mark where Nashville is, but the pirates go on an island where there is an A marked on the ground. Then they go to various islands with different letters of the alphabet marked and finally go to an island with an X marked on the ground. At first, Timon gets angry at the pirates for not going to Nashville until Pumbaa tells the meerkat that there is treasure buried in the sand under the X, which makes Timon excited and pull out a shovel from his suitcase and dig.
After Timon takes out the treasure, the pirates, knowing that they are dimwitted, decide to bury the treasure. Timon and the pirates start to fight over the treasure. Timon then decides to protect the treasure by putting pillows, horseshoes, and other things under the chest while the meerkat stands on it dressed in army clothes and holding a gun. Then it gets dark and the pirates are sleeping while Timon is still doing his job. Then morning comes and Timon falls asleep, but then falls off the treasure and everything falls on the pirates.
The pirates get out of the sand, but then the sand explodes. Timon then gives up his job as the pirates' captain and he and Pumbaa decide to go to Nashville on their own. When Timon and Pumbaa finally get to Nashville, they perform a cowboy dance in front of a live audience, who are all dressed as pirates. After the audience cheer for the duo, the pirates show up with their ship and do their show while Timon passes out and Pumbaa looks at the audience cheering for them. It's then revealed that Timon and Pumbaa are at a pirate convention and the audience are real pirates.
- Interestingly, the pirate with the bandana made his first appearance in "Shopping Mauled" and the Jamaican pirate made his first appearance in "Library Brouhaha".
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