Rupert’s back in Rocky Bay, this time to visit 3 very unusual old friends — Tom, Mr. Ribbons, and Bill Bottles, all elderly former pirates. Once fearless adventurers who sailed the Spanish Main, they’re too old now to do anything but sit in their rocking chairs in a rundown shack they rent from local scoundrel Mr. Eel. Or so they think until Rupert finds a map to a treasure of their old rival hidden in the model ship they give him. Ignoring Bill’s insistence that they’re too old for adventure now, the trio accompanies Rupert on a quest to find the treasure on a nearby island, stalked every step of the way by Eel.
This episode provides examples of:
- A Pirate 400 Years Too Late: Rupert’s pirate friends are old and retired, but there’s no way they were alive centuries ago, so they clearly count.
- Cool Old Guy: The three retired pirates prove themselves this in the final battle with Eel and his henchman.
- Cranky Landlord: Mr. Eel is basically a slum lord for Rupert’s three friends.
- Dressed to Plunder: Interestingly, Bill is strongly against the team going on another adventure, but he’s also the only member of his team who still dresses like an active pirate...
- Eyepatch of Power: Bill, who seems to have been the trio’s captain, wears one.
- I Don't Like the Sound of That Place: Dead Man’s Drop. (No, Rupert, it’s not just a name.)
- MacGuffin Delivery Service: Mr. Eel intends to follow the heroes and let them find the treasure for him, then steal it.
- Older Hero Versus Younger Villain: Three old men vs. the younger Eel.
- Pirate Booty: The goal of the episode is to find the buried treasure.
- Pirate Parrot: The heroes find one at Spyglass Point, who tags along and proves useful at creating distractions.
- Rags to Riches: With the treasure, Rupert and his three friends found the Rocky Bay Home For Retired Pirates, where the trio who were previously living in poverty can now live (along with many others) in comfort.
- Retired Badass: The episode is all about 3 of them rediscovering their strength and love for adventure.
- Rousing Speech: When they see Eel managed to keep up with them the entire time despite Rupert’s tricks, Tom and Mr. Ribbons are ready to give up and let him have the treasure. Bill Bottles rallies them with one of these, his faith in himself and his friends restored by reaching their goal.
- Ruthless Modern Pirates: Mr. Eel, according to Bill.
- Talk Like a Pirate: All three of the retired pirates still talk like this.
- This Is No Time for Knitting: After the group falls into an underground river, lost in a maze of tunnels, Rupert starts folding the map into a paper boat. Bill Bottles tells him, “This be no time for games, lad,” but Tom tells them to wait and see his plan. As Rupert predicted, with the boat in the water, they’re able to see the current and follow it out.
- Treasure Map: Rupert finds it hidden in a model ship.
- Vine Swing: Simultaneously Invoked and Defied. After the group shimmies across a canyon on a long tree branch, Rupert ties one end of a vine to a wasp nest and throws the other end to the other side. The trap works perfectly — Mr. Eel assumes they swung across, tries to do the same, and disaster ensues.
- We Need a Distraction: Rupert has their new talking parrot friend lead Mr. Eel and his sidekick on a false trail.
- "X" Marks the Spot: Since it’s carved into solid rock, the trick isn’t so much finding it as it is finding out how to get inside what it’s covering.
