"Darkwing Doubloon" is the 40th episode of Darkwing Duck.
Darkwing tells a tale of an ancestor from three centuries prior named Darkwing Doubloon. The scene cuts to the royal family's ship with Seaman Drake handling the ship for the royal family a.k.a. the Muddlefoots. The ship is attacked by Negaduck and his pirate gang which includes Megavolt, Bushroot, Quackerjack and the Liquidator. They take the royal jewels and Negaduck tells them that he is a better pirate than the infamous Darkwing Doubloon.
After the pirates have left, Drake tells the Muddlefoots that the ship is sinking and that he will go down with the ship while they get away on a lifeboat. It was all just a ruse so Drake could become Darkwing Doubloon and use the ship. He gets his crew, which includes Gosalyn, Launchpad, Gizmoduck, and Stegmutt. They set sail to find Negaduck and retrieve the jewels. They find them and board Negaduck's ship. As they are fighting, Gosalyn goes into Negaduck's quarters and takes the treasure and hands it out to the crew a little at the time and they sneak it back to their ship. Just as she hands the last of it to Stegmutt, she gets trapped in the chest and locked in. Darkwing acts as if he has been beaten and is thrown overboard.
Back on the ship Darkwing realizes that Gosalyn is not there and knows that he must get her back. Gosalyn is discovered by Negaduck and he uses her as bait. Darkwing catches up to Negaduck and trades the treasure for Gosalyn who has secretly stolen Negaduck's map to his island. They are tricked and Negaduck sinks their ship and gets the treasure. Darkwing thinks that all is lost but Gosalyn tells him that he should not give up and they use Stegmutt for a boat and Gizmoduck provides propulsion and they use a map that Gosalyn stole to find Negaduck's island hideout. The Fearsome Pirates make it to the island and are bringing the treasure into his cave. As they sing in victory, they are ambushed one by one by Darkwing and his crew, until Negaduck is the last one standing, much to his suspicious notice that he stopped singing in victory. He and Darkwing face off and Darkwing is triumphant in the end. Drake returns Negaduck's ship and the treasure to the royal family with The Fearsome Pirates as prisoners. Negaduck threatens Drake and Drake threatens to summon the Darkwing Doubloon. Negaduck's crew tells him to be quiet.
Darkwing: What a Willy Wonker.
- (Negaduck is forcing Darkwing down the plank with his sword)
- Negaduck: Any last words, Baboon?
- Darkwing: That's Buffoon, (Corrects himself) I mean, Doubloon. D-O-U-B-L...Whoa! (Falls into the ocean)
Quackerjack: Ship off port! (Giggles a bit) It's playtime!
- Darkwing: Unhand my crew member and I might let you live.
- Negaduck: (Holding Gosalyn hostage) I don't think so, Buffoon.
- Gosalyn: Oh, he means it, Doubloon. Oh, and don't get spirited. He hates that.
- Gosalyn: (Dizzily, groans a bit) Rough seas.
- Negaduck: And they're going to get a lot rougher for you, little sailor.
- (Megavolt pulls his electric sword out, only to reveal that it’s bladeless due to not being activated)
- Drake: (Laughs) You forgot the rest of your sword, cur.
- Megavolt: I think not.
- (He activates his electric sword’s blade and aims it threateningly at Drake, who gets nervous)
- Drake: (Chuckles nervously, reluctantly hands some treasure to Megavolt) Here, let me lend you a hand.
- Gosalyn: (Cornered by the Fearsome Pirates, stammering) All right. You back off and I'll go easy on you.
- (Negaduck appears in front of her and points his sword at Gosalyn)
- Negaduck: You're being spirited again.
- Liquidator: He hates that.
- Gosalyn: (Gulps) I know.
- Negaduck: (Upon catching Gosalyn in his cabin after she successfully stole his map) Well, well. What do you have to say for yourself?
- Gosalyn: You call this a pirate cabin? My room's a lot scarier.
- Negaduck: (Dumbfounded) Huh? (Angrily indignant) Hey! What's wrong with my cabin?
- Darkwing: We lost the King's jewels, the King's ship and my reputation as Sourge of the Seven Seas!
- Stegmutt: We still think you're a scourge.
- Launchpad: Yeah, you're the worst.
- Darkwing: You know, you're right. I am. (Chuckles a bit) And by gosh, I'm going after Negaduck!
- Gosalyn: And I know right where to find him. (Shows map)
- Gizmoduck: You stole Negaduck's map, Gos?
- Gosalyn: I just borrowed it a little.
- Darkwing: All's fair with pirates, Giz.
- Negaduck: Now we got us some Darkwing Doubloon bait!
- Gosalyn: You'll have to catch me first!
- Negaduck: Spirited, eh? (Laughs sadistically a bit) I hate that.
- Negaduck: I, Negaduck, have defeated the great Darkwing Doubloon once again!
- Megavolt, Quackerjack, Bushroot, and Liquidator: (Flatly) Yay.
- (Negaduck and his crew are tied up and imprisoned by Seaman Drake upon their defeat by Darkwing Doubloon)
- Negaduck: Don't think you can keep us here, you royal dinghy keeper.
- Drake: Quiet! Or I'll summon the Darkwing Doubloon.
- Megavolt, Quackerjack, Bushroot, and Liquidator: (Glaring at Negaduck) Yeah, quiet!
- (Drake closes the trapdoor the pirates are imprisoned in with a slam)
- Drake: Yep, yep, yep. Still Scourge of the Seven Seas.
- Megavolt: (After almost getting splashed by Liquidator while steering Negaduck's ship) Get any water on me, and I'll evaporate ya!
- Liquidator: (Swabbing the deck, glares daggers at Megavolt) You and what navy?
- Quackerjack: (Calls down to them from the crow's nest) Keep it down! Negaduck's on deck.
- Bushroot: (Sarcastically) Ooh, look at me. I'm shaking like a leaf.
- Negaduck: (Glaring at Bushroot) I hope it's not on my account, Bushroot.
- (Bushroot gets scared and grovels at Negaduck's feet)
- Bushroot: Oh, no, no, no, Captain.
- Negaduck: (Growls angrily a bit) Drat! We can't go to our island and hide the treasure as long as that Darkwing Buffoon sails the seas.
- Gosalyn: (Removes her gag cloth from her mouth due to being tied to a mast) Oh, you've got an island. So, that's where you keep your treasure, huh?
- Megavolt: Aye, you bet we do, missy.
- (Negaduck goes up to Megavolt's face in anger)
- Negaduck: You just told her about the map.
- Bushroot: Ha! And he almost told her it's in your cabin under the sextant.
- Negaduck: WHAT ARE YOU DUCKHEADS DOING?! (Pulls his sword out, scaring Megavolt, Quackerjack, Bushroot, and Liquidator and making them run and him giving chase while Gosalyn secretly frees herself) Come over here! I'm going to get you!
Drake: (To the audience, narrating) Little do they know.... And I mean that!
Darkwing: I am the terror that sails the seas. I am the flea on your parrot. I am the Darkwing Doubloon!
- (The Fearsome Pirates have arrived on their island hideout and are walking to their island cave hideout to hide the stolen treasure)
- Negaduck: We just won a great victory! And I don't hear any pirates singing.
- (He and his crew sing to a tune parodying "99 Bottles of Beer on the Wall" as Darkwing and his crew prepare to secretly capture them)
- Fearsome Pirates: Pirates are something to fear on the sea
- Pirates have something to fear
- (Stegmutt secretly snatches away a treasure chest from Quackerjack and then Launchpad captures Quackerjack by pulling him away by his beak)
- Negaduck, Megavolt, Bushroot, and Liquidator: Pirates have something to fear on the sea
- Pirates have something to fear
- (Bushroot then falls into Darkwing's crew's pit trap, unknown to Negaduck, Megavolt, and Liquidator, and Gosalyn snatches a bag of treasure Bushroot dropped)
- Negaduck, Megavolt, and Liquidator: Take a ship, sink a ship
- Take the jewels, pirates have something to fear on the sea
- (Gizmoduck then secretly absorbs Liquidator onto a giant sponge after knocking a treasure chest he's carrying aside)
- Negaduck and Megavolt: Pirates have something to fear on the sea
- Pirates have something to fear
- Take the jewels....
- (Darkwing lastly lassos Megavolt away, along with two small bags of treasure the latter's carrying)
- Negaduck: (Arriving at the cave) Pirates have something to fear on the sea....
- (He slowly finishes singing in suspicion upon entering his cave)
- Negaduck: Pirates, I don't hear....
- (He then sees Darkwing in there, holding a lit candelabra)
- Negaduck: (Surprised) Doubloon?!
- Darkwing: Like a night, Negaduck, the Darkwing Doubloon returns.
- The pirate song the Fearsome Pirates are singing a tune to near the end of the episode is a parody of "99 Bottles of Beer on the Wall."
- As Darkwing Doubloon's ship reverses direction when Negaduck's ship attempts to crash into it, just as the ship jumps up from the water, you can hear a Goofy holler coming from Launchpad.
- When the royal family (The Muddlefoots) board the liferaft, you can see the outline of Darkwing's face mask on Seaman Drake.
- Megavolt is briefly wearing his modern day jumpsuit instead of his pirate attire in one shot while Bushroot spilled the beans about Negaduck's treasure map being in his cabin under his sextant.
- When Launchpad is fighting Liquidator for the first time, Liquidator has an earring and then it disappears in one shot.
- With the door hinges on Negaduck's cabin on the inside, Launchpad should not have been able to open the door outwards when they were smuggling the jewels off Negaduck's ship. Stegmutt does the same thing when he leaves the cabin and then the door disappears for a second.
- Quackerjack is the only character not to get an alternate costume for this episode. This might be because his jester outfit already works for the time period, but at the same time it’s ironic because Quackerjack is the character known for loving dress-up.