Properly titled "Doctor Who And The Pirates [[EitherOrTitle or]] The Lass That Lost A Sailor".

One of the most well-loved AudioPlay/BigFinishDoctorWho episodes, and certainly one of the Sixth Doctor's most popular episodes ever made. The (intentionally awkward) title is a parody of both [[Recap/DoctorWhoS7E2DoctorWhoAndTheSilurians "Doctor Who And The Silurians"]] and ''Theatre/HMSPinafore or The Lass That Loved A Sailor''.

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Sally, a history student, is having a hard time, and the ''last'' thing she wants today is for her favourite tutor, Dr. Evelyn Smythe, to turn up and tell her a long, rambling story about pirates.

But Dr. Smythe won't be dissuaded. In fact, she even invites her friend and travelling companion, the Doctor, into Sally's apartment so they can ''take turns'' with the pirate story. Evelyn insists the whole story is true, even though Sally points out that it's a transparent SelfInsertFic set in a mess of pirate cliches.

As the story goes on, though, Sally starts to see some uncomfortable similarities to her own life. In particular, to a very recent, very painful, very personal loss... someone very dear to her was killed in a car crash. Sally was driving. And she doesn't think she can go on.

The pirate story starts getting darker, too, so the Doctor decides that the only way to cheer them all up is... to [[CrazyAwesome turn it into a musical!]] A Creator/GilbertAndSullivan one, to be exact.

The story deals with a pirate captain named Red Jasper, who's after a map leading to a treasure. A cabin boy named James London (Jem for short) turns out to be the son of the only man who knew its location. Evelyn and Jem are captured by Red Jasper, and despite Evelyn's best efforts to bluff her way out (posing as "Evil Evelyn, the Pirate Queen"), Jem is tortured and brutally murdered. Evelyn blamed herself for his death, and asked the Doctor to take her home after the adventure was over. When she got home, she found Sally's suicide note in the mail. She asked the Doctor to take her back in time so they could talk Sally out of it.

Although Sally isn't sure what to make of the story in the end, Evelyn manages to explain to her that real life doesn't have a happily ever after -- just good days and bad days. And that as long as one person cares, life is worth living.

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This episode is directly followed by [[Recap/BigFinishDoctorWhoSpecialsRealTime "Real Time"]].

!!Tropes:
* AnachronismStew
* AnythingYouCanDoICanDoBetter: The Doctor and Merryweather have a song about this.
* AristocratsAreEvil: Captain Swann isn't evil so much as spoiled and useless.
* AsYouKnow
* AxeCrazy: Red Jasper
* BatmanGambit: The Doctor lets Merryweather challenge him to a rum drinking contest, followed by a plank walking contest. Merryweather, lacking the Doctor's Time Lord constitution, gets drunk off his face and falls right off the plank.
* BoardingParty
* BreakTheCutie: Evelyn suffers due to the subject matter in this story, despite making it LighterAndSofter.
* BuriedTreasure
* CanonDiscontinuity: The Doctor, InUniverse, wonders to himself if [[Series/K9AndCompany Hecate]] is in continuity.
* {{Cliffhanger}}: After a few hints and hums from the Doctor, episode 2 ends with the following exchange...
-->'''Doctor''': Why, you could almost say I was the very model of a Gallifreyan buccaneer. ''[song cue begins to play]''
-->'''Evelyn''': Oh no! You ''are'' going to sing!
-->'''Doctor''': Well, yes! I am! ''Llllllllllllllaaaaaaaaaaaaaaaaaaaa-[[[InterruptedByTheEnd Theme music plays. Episode ends]]].''
** And then he gleefully sings it as soon as the next episode starts.
* ContinuityNod: The Doctor credits Mel's exercise regime for his excellent physical form.
** Evelyn also mentions he doesn't like talking about [[Recap/DoctorWhoS19E4TheVisitation the Great Fire of London]].
* ContinuityPorn: The Doctor's "buccaneer" song namedrops [[Recap/DoctorWhoS1E2TheDaleks Daleks]], [[Recap/DoctorWhoS6E1TheDominators Quarks]], [[Recap/DoctorWhoS4E2TheTenthPlanet Cybermen]], [[Recap/DoctorWhoS3E4TheDaleksMasterPlan Mavic Chen]], [[Recap/DoctorWhoS6E3TheInvasion Tobias Vaughn]], [[Recap/DoctorWhoS7E1SpearheadFromSpace Autons]], [[Recap/DoctorWhoS8E3TheClawsOfAxos Axons]], [[Recap/DoctorWhoS3E6TheArk Monoids]], [[Recap/DoctorWhoS18E4StateOfDecay Vampires]], [[Recap/DoctorWhoS1E5TheKeysOfMarinus Voords]], [[Series/K9AndCompany Hecate]], [[Recap/DoctorWhoS20E2Snakedance Manussa]], [[Recap/DoctorWhoS6E1TheDominators Dulkis]], [[Recap/DoctorWhoS17E5TheHornsOfNimon Skonnos]], and [[Recap/DoctorWhoS18E2Meglos Tigella]].
* CreditsGag: The final credit theme is rewritten as a Gilbert & Sullivan pirate tune.
* TheDragon: Merryweather
* DarkReprise: The song Pirate Queen first shows up when Evelyn and Red Jasper are singing about the virtues about being a Pirate Queen and King, respectively. The dark reprise occurs not 5 minutes later when Jasper sings it again, celebrating his complete authority [[spoiler: after cutting out the tongue of one of his crew and pushing the Doctor off the plank.]]
* DrinkingContest
* DrivenToSuicide
* TheDrunkenSailor
* DuelToTheDeath
* EitherOrTitle
* EyepatchOfPower: Red Jasper.
** Also more than likely, One-Eyed Trent.
* FlashbackWithinAFlashback
* FramingDevice: The Doctor and Evelyn tell Sally a story.
* GiverOfLameNames: Evelyn names all the new pirates with the same idea. John Johnson, Bill Billson, Thom Thomson.
* HairTriggerTemper: Red Jasper.
* HamToHamCombat: Creator/ColinBaker's Sixth Doctor versus Bill Oddie's Long John Silver {{expy}} Red Jasper.
* HardGay: Mr. Mate. Supposedly.
* HookHand: Evelyn inintially claims Red Jasper has two hooks for hands. When Sally points out that he would not be able to fire a pistol, Evelyn admits she was embellishing, but it is not clear if Jasper has one hook or none.
* [[ImADoctorNotAPlaceholder I'm A Historian Not An Impressionist]]
* InexplicableTreasureChests: Played with -- Evelyn invents some treasure for the ''Sea Eagle'' to be carrying, so it'd sound more like a pirate story.
* InnocentInnuendo:
--> Captain Swann: "''I'' should be doing all the stroking."
* InTheBack
* KarmaHoudini: Capt. Swann.
** Red Jasper, who gets off ''much'' easier than other Doctor Who villains who commit equivalent crimes.
* LeaningOnTheFourthWall
* LighterAndSofter: InUniverse, Evelyn starts making the story "more fun" once she realizes it's actually a pretty dark tale.
* MementoMacGuffin / OrphansPlotTrinket: Jem's compass.
* MobileShrubbery / TrojanHorse: The Doctor and Evelyn hide in barrels, hoping to get taken aboard Red Jasper's ship as booty. [[{{SubvertedTrope}} It doesn't work.]]
* MoodWhiplash: An light-hearted romp set during the golden age of piracy gets pretty damn dark before the eventual dawn.
* MusicalEpisode: And all acquit themselves very well!
** IAmSong: First by the Doctor with "I am the Very Model of a Gallifreyan Buccaneer" and then by the pirates with their "An Assassin's Lot is Not a Happy One."
** IWantSong
** MajorGeneralSong
* MusicalisInterruptus
* TheMutiny
* NewerThanTheyThink: All the PirateTropes get [[LampshadeHanging lampshaded]] and pointed out by Sally, who blames most of it on TreasureIsland.
* ObviouslyEvil: Evelyn is trying to make sure Red Jasper is considered the bad guy by giving him every RedRightHand she can think a pirate should have.
* PatterSong: "[[http://www.youtube.com/watch?v=hIdDXQ2h1Pc I Am the Very Model of a Gallifreyan Buccaneer]]"
* PepperSneeze
* PyrrhicVictory
* PirateBooty
* PirateGirl: The Doctor claims Evelyn is "Evil Evelyn, the Pirate Queen". The masquerade works... briefly.
* RecordNeedleScratch
* SelfInsertFic: Sally accuses Evelyn of this.
* ShaggyDogStory
* ShoutOutToShakespeare: "[[Theatre/MacBeth All the perfumes of Arabia will not sweeten this little hand]]."
* ShoutOut: See also GiverOfLameNames: among those names are Literature/NicholasNickleby, Literature/OliverTwist and Literature/DavidCopperfield.
* SissyVillain: Captain Swann.
* SomethingOnlyTheyWouldSay
* SpotOfTea: Evelyn insists on making multiple cups of tea for Sally.
* {{Sting}}
* SurvivorGuilt
* {{Swashbuckler}}
* TalkingToHimself:
--> '''Sally''': "Hey that's the same man!"
--> '''Evelyn''': "No it's not. Anyway, [[ImADoctorNotAPlaceholder I'm a historian, not an impressionist]]."
* TalkLikeAPirate
* [[BeethovenWasAnAlienSpy Tarzan Was The Doctor]]: Actually a lie, and he gets called out on it.
* TimeSkip: Justified seeing as it's a story being told.
* TreasureMap
* UnreliableNarrator: Evelyn. The Doctor as well.
** Note Red Jasper changes from "Horrible coat" to "Stylish outfit" in between the two.
* UpperClassTwit: Captain Swann
* WalkThePlank
* WouldHitAGirl: Red Jasper.
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