[[caption-width-right:291:Buggers with style.]]

''Plunkett & Macleane'' is a historical action comedy, released in 1999. The titular characters are based very, [[VeryLooselyBasedOnATrueStory very loosely]] on real life [[TheHighwayman highway men]] William Plunkett and James Macleane. The story itself? Pretty much nothing to do with them.

Set in 1748, when highwaymen are plaguing the wealthy along England's roads, the film a revolves around the criminal partnership of the titular characters. Macleane (Creator/JonnyLeeMiller) witnesses a robbery gone wrong when Plunkett's young partner is killed by Thief Taker General Chance. Desperate to clear his debts, Macleane attempts to retrieve a valuable ruby the deceased partner swallowed before his death. Unfortunately at the cemetery he's confronted at gunpoint by Plunkett (Creator/RobertCarlyle). Things take a bad turn for both parties when Chances men arrive to arrest them forcing Plunkett to swallow the ruby before their capture.

Realising Macleane's higher social status will allow him the means to bribe them both out of prison with the jewel, Plunkett proposes a new partnership. Macleane begins living among the rich, gaining inside knowledge so Plunkett can figure out how to rob them blind. Beginning a lucrative and highly risky business venture together. As their notoriety spreads, General Chance grows more eager to catch them in the act and Macleane begins to complicate things further by falling for one Lady Rebecca Gibson (Creator/LivTyler).

As a whole the film is your classic tale of unlikely partners becoming friends that just happen to be criminals in the 18th century. Expect [[RuleOfCool entertainment]] and [[RuleOfFunny humour]] to take precedent over strict historical accuracy.
!!Tropes Used:

* AbsurdlySpaciousSewer: Used to escape on several occassions by the highwaymen.
* AllGirlsWantBadBoys: Lady Rebecca, of course. One woman ''in the middle of being robbed'' no less, was enjoying things a little too much...
* AlwaysSaveTheGirl: Subverted. [[spoiler:Macleane goes back for Rebecca, despite Plunkett's warnings its a trap. In the end it gets him arrested and convicted for murder]].
* [[AntiHero Anti Heroes]]: Plunkett & Macleane, despite being thieves come off very heroic, especially given the evil Chance is hunting them and the people they steal from are mostly elitist snobs.
* AnythingThatMoves: Rochester
-->'''Macleane''': Still swinging both ways, Rochester?
-->'''Rochester''': Jamie, I swing ''every way''.
* AssholeVictim: Rooting for the two rather unscrupulous highwaymen -- other than the fact that [[JerkWithAHeartOfGold they both turn out to be not quite so unscrupulous after all]] -- is certainly made a lot easier by the fact that the people who they steal from are pretty much uniformly complete and utter dickwads.
* BecomingTheMask: Macleane's love of excess and playing the rich boy start to get the better of him.
* BigBad: Thief Taker General Chance.
* [[BigDamnHeroes Big Damn Hero]]: [[spoiler: Plunkett]] has a glorious example of this.
* BlackComedy: Along side the light humoured stuff, there's some pretty grim humour too.
* DancesAndBalls: A brief but no less elaborate ball is held midway through the movie.
* DefiantToTheEnd: Despite [[spoiler:the fact Macleane is about to be wrongly sentenced to death for murder]], he regrets only one thing. And lets the Lords, Ladies and Judge watching know it.
-->[[spoiler: '''Macleane''']]: I am guilty of one thing for which I am heartily sorry. Namely [[spoiler: cheating my friend and fellow highwayman]]. A man who has more nobility of soul, in his little finger, than any of you bloated bastards have in your entire bodies.
* DuelToTheDeath: In the form of 'Pistols at Dawn' [[spoiler: subverted in that neither Chance nor Plunkett die. Chance cheats to avoid death whilst Plunkett is only wounded]].
* TheDungAges: The peasantry are shown to live in some pretty flithy and harsh conditions, which is likely accurate for the very poor of the time. In deliberate [[GorgeousPeriodDress contrast]] to the nobility and filthy rich.
* EyeScream: Plunkett's dying partner falls victim to this, courtesy of Chance.
** [[spoiler:Will returns the favour with a [[MoeGreeneSpecial bullet at point blank range]]]].
* FatalFlaw: Macleane loves women and gambling. You'll never guess what gets him in trouble.
* ForcedToWatch: As if we didn't have ''enough'' motivation to hate Chance, he forces Rebecca to watch as [[spoiler:Macleane is hanged]].
-->'''Chance:''' Open your eyes!
* GentlemanSnarker: Lady Rebecca Gibson is a female example. She is described by [[AnythingThatMoves Rochester]] to be "very choice, very choosy" when it comes to her long line of unsuccessful suitors, sending one off in the same scene with a particularly barbed remark. Though unheard by the audience, the reaction of the suitor indicates the remark was particularly vicious, though probably deserved.
** Even with the man she likes, her initial flirting has a particularly snarky and mischievous tone.
--> '''Lady Rebecca:''' ''(to Macleane)'' You are ''not'' a gentleman.
--> '''Macleane:''' I'm sorry?
--> '''Lady Rebecca:''' No gentleman would stare at a lady like that in public.
--> '''Macleane:''' I do beg your pardon. Captain James Macleane, at your service.
--> '''Lady Rebecca:''' Oh, so you are a gentleman?
--> '''Macleane:''' Yes.
--> '''Lady Rebecca:''' What a shame.
* GoodTimesMontage: The duo rack up a shitload of heists and money. Unfortunately a darker undercurrent begins to show as [[spoiler: Macleane's pissing it all away on gambling]].
* GorgeousPeriodDress: It is the 18th Century nobels being robbed after all.
* GunsAkimbo: Hell yes. Complete with Badass posing.
* [[TheHighwayman The Highwaymen]]
* HistoricalDomainCharacter: Sort of. Rochester is presumably a reference to [[http://en.wikipedia.org/wiki/John_Wilmot,_2nd_Earl_of_Rochester John Wilmot, Earl of Rochester]], who was likewise an AnythingThatMoves kind of guy, although that Rochester lived around a century before the setting of the film. Likewise, Plunkett and Macleane themselves are inspired by actual highwaymen.
* HonorAmongThieves: Plunkett swears revenge for his partners death early on and then [[spoiler:saves Macleane ''despite'' him bringing his hanging on himself and spending all their money]]. Macleane doesn't share this this sentiment initially [[spoiler:but comes to respect Will and regret his selfish actions later on. Even coming back with Rebecca in the tunnels to save Plunkett from Chance's men]].
* HonorBeforeReason: Plunkett [[spoiler: when he allows Chance his shot in a duel. Despite having every right to deny him, since the general cheated, simply to show him he was the better man]]. In fact Plunkett's sense of honor causes [[spoiler: the above duel]] in the first place.
* IHaveYouNowMyPretty: Chance acts this way towards Rebecca, who is digusted by his very presence.
* ImprobableAimingSkills: Plunkett. Especially when combined with his trademark crouch dodge. At least when you consider he's using smooth-bore guns.
* KickThemWhileTheyAreDown: Chance is very fond of this.
* LaserGuidedKarma: [[spoiler: Chance is killed with a bullet through the eye whilst trying to gouge out someone else's ''again''. Justified in that Plunkett lured him into the situation and probably shot him there in retribution for his ex-partner]].
* LoveableRogue: Macleane. He's a bit of dick with a gambling problem but he ''still'' comes off as likeable.
* MoeGreeneSpecial: [[spoiler:How Plunkett finally takes Chance down]].
* MrFanservice: Macleane obviously. However Plunkett has a different appeal. Rochester calls him a "delicious bit of rough," and after Plunkett's honourable performance during [[spoiler: the duel with Chance]], news of his bravery (and his visible injury) lead to some marked interest from a few of the ladies in Macleane's acquaintance.
* NameAndName
* PlayingPossum: Used to lethal effect by [[spoiler: Plunkett. Who kills Chance when he lets down his guard to try and torture him]].
* PocketProtector: An odd villainous example [[spoiler: Chance survives the duel with Plunkett because he kept a bible over his heart and even declaring ''Thank God'' despite clearly being a cowardly cheat]].
* PreMortemOneLiner:
-->[[spoiler:'''Chance''']]: Does that hurt?
-->[[spoiler:'''Plunkett''']]: ''*Grinning*'' Only when I laugh. ''*BANG!*''
* {{Revenge}}: Plunkett swears this on Chance.
* RobbingTheDead: James tries this to obtain the ruby at the cemetary, Will's having none of it.
* RoyalBrat: A lot of the rich victims are nothing more than vain spoilt brats.
* ShootTheRope: [[spoiler: How Plunkett saves his partner Macleane from hanging during the finale]].
* SociopathicHero: Plunkett has elements of this.