The Wettest Stories Ever Told is the eighteenth episode of The Simpsons' seventeenth season. This is one of several Simpsons episodes which are considered anthology episodes that features mini-stories.
When dinner at the Frying Dutchman takes a little longer than expected to cook, thanks to an uncooperative octopus armed with knives, and the Sea Captain doesn't know any sea tales, the Simpsons take up the slack by telling stories of three famous ships; Lisa with the Mayflower, Bart with the Bounty, and Homer with a ship that sounds an awful lot like the Posiedon (and is even named for a god of the sea, albeit the Roman one).
Marge (who's a widow) and her two children, Bart and Lisa, board the Mayflower to head for the new world, but just as they do, Homer runs ahead of them and hides in a barrel. Marge, Bart and Lisa see that he's wanted by the police (Lenny Leonard and Carl Carlson) for questioning on why the current time period is called the Jacobean era when the King's name is James rather than Jacob, and the family takes pity on him. Marge and Homer start to like each other, but Moe, who also likes Marge, instantly becomes jealous of their friendship. To get Homer out of the way, Moe takes him down to the storage room where all the beer is held and tells him to drink whenever a wave hits the boat. He gets drunk, and Captain Flandish and Reverend Lovejoy find him and other passengers partying.
Moe blames Homer, and they place him in a stock. A storm then approaches, and Captain Flandish becomes unconscious. Homer claims that he's actually a good driver when he's drunk (claiming that he's been driving drunk since he was just twelve), and while drinking a bottle of wine while still trapped in the stock and shirtless, he leads them safely out of the storm, and he and Marge become an official couple. All members of the Mayflower meet the Wampanoag tribe, and Flandish thanks Great Chief Wig-Gum for all he has done for them, as he regrets for what they are going to do to them. Wiggum then asks what that is, and Flandish replies it is giving him the biggest piece pumpkin pie, and mumbles that they are going to take their land and wipe them out.
The Bounty sets sail from England in 1789, commanded by Captain Bligh. During the first 718 days of the voyage, Bligh severely mistreats his crew, such as by not giving them water at last day in order to save water and tossing off their mail because they had drawn a picture of Bligh making out with a merman. Willie warns him of a mutiny if he mistreats them too much, but Bligh ignores him. They arrive in Tahiti, where Homer and Marge are the rulers of island and the crew has a wonderful time until it was time to leave. The crew wanted to stay at Tahiti, but Captain Bligh tells them that it was wonderful vacation but they must forget it and sing "Row, Row, Row Your Boat" in-a-round while working.
Eventually, Bligh continues abusing the crew more as they sing, and First Mate Bart Christian, who had enough of this, leads a mutiny with the help of the crew and sends Bligh and Willie off in a lifeboat. Willie then berates Bligh for not listening to him in the first place, but that only makes Bligh more angry at Willie, challenging him as too much of a spineless coward to mutiny. In response, Willie forces Bligh off the lifeboat (proving that he is not a coward) and rows away while Bligh holds onto on a sea turtle, who then submerges into the sea, with Skinner in tow after the latter taunts it. Bart, as the new Captain of the Bounty, orders the crews to set sail for Tahiti. Then he throws away the ship’s helm and they crash into Antarctica.
Homer’s story takes place on the luxury liner S.S. Neptune on New Year’s Eve during the 1970s. At midnight, Captain Burns fails to notice a massive freak wave which hits the bridge and kills him and First Officer Waylon Smithers and the ship capsizes. Led by Selma, survivors Homer, Marge, Bart, Lisa, Lenny, Carl, Comic Book Guy, Old Jewish Man and his wife, and Sideshow Mel ignore Purser Wiggum’s advice to stay put in the ballroom and decide to climb up the decks to the engine room. While climbing up through the smokestack, Lenny panics and takes a dive.
They encounter rooms in flame, tigers, and Homer doing his business in an upside-down bathroom, knowing that he has great "ass-suction". Comic Book Guy swims through a flooded deck to help the others get to the engine room, but he has a heart attack and dies. The group makes it to the engine room, but Sideshow Mel’s hair is set on fire because of a blowtorch from the rescue team and he falls unconscious. The rest of the original group makes it off the ship, at which point they encounter the walking skeletons of the Bounty crew who are still trying to get back to Tahiti.