Plunkett & Macleane

1748 England is infested with highwaymen — men such as Will Plunkett (Robert Carlyle), a London-based criminal working with his partner Rob (Iain Robertson). When Rob is killed by thief-taker General Chance (Ken Stott) after a botched heist outside debtor's prison, Plunkett must find a way to retrieve a large ruby that his partner had swallowed. What he doesn't know is that the incident was witnessed by James Macleane (Jonny Lee Miller), a socialite from the upper echelons of society, who had found himself in debtor's prison. Macleane sees this ruby as his ticket out of debt and decides to steal it.

Plunkett ambushes Macleane and forces him to give up the ruby, but when they are discovered by Chance's men, Plunkett swallows it. While in Newgate Prison, the two form a partnership that utilizes Plunkett's criminal know-how and Macleane's social status to bribe their way out of prison. This tentative partnership leads to an unlikely alliance, deemed "The Gentlemen Highwaymen", where they gladly relieve the gentry of their possessions.

When Macleane falls for the beautiful Lady Rebecca (Liv Tyler), the niece of the powerful Lord Gibson (Michael Gambon), their plans to escape to America go awry. The pair part ways after a disastrous attempt to rescue Lady Rebecca from forced exodus, which leads to the death of Lord Gibson, and the discovery that Macleane has gambled away all of their funds.

Macleane is eventually captured and tried for Lord Gibson's murder, earning him a date with the gallows. Plunkett orchestrates a daring escape, aided by Lady Rebecca and the flamboyant Lord Rochester (Alan Cumming). After a tense chase through the city sewers that sees Plunkett exact revenge upon Chance, the three escape to freedom.

• Jonny Lee Miller as Captain James Macleane
• Robert Carlyle as Will Plunkett
• Liv Tyler as Lady Rebecca Gibson
• Ken Stott as Thief Taker General Chance
• Alan Cumming as Lord Rochester
• Michael Gambon as Lord Gibson
• Tommy Flanagan as Eddie
• David Walliams as Viscount Bilston
• Matt Lucas as Sir Oswald
• Ben Miller as Dixon
• Stephen Walters as Dennis
• Alexander Armstrong as Winterburn
• Noel Fielding as Brothel Gent
• Nicholas Farrell as M.P.'s Secretary
• Iain Robertson as Rob
• Claire Rushbrook as Lady Estelle
• Tom Ward as a member of parliament

Plunkett & Macleane underperformed at the US box office.[6] The film opened on 1 October 1999 in 475 U.S. theaters, taking in $244,765 during its first three days; total US earnings stand at $474,900.[7]

The film received mainly negative reviews from critics, Rotten Tomatoes lists a 24% critic rating from 29 critics,[8] while Metacritic's Metascore is 44 from 27 reviews (indicating "mixed or average reviews").[9]

Derek Elley of Variety wrote, "[T]he script and dialogue are nowhere near well-tooled enough, and the film's generally dark, cold look and baroque design play against the lighter touch required. Though he certainly puts the reported $15 million budget up on the screen, helmer Jake Scott (son of Ridley Scott) seems happiest when pushing ahead to his next montage sequence, each of which has the brio that should have informed the whole movie. [¶] Carlyle, with a convincing cockney accent, and Lee Miller, as the rumpled pretender, are strong, with considerable chemistry between them. Though she's clearly spent time on her English vowels, Tyler is only adequate as Rebecca, a well-bred young lady who's intrigued by Macleane's derring-do. Making the biggest impression, in smaller roles, are Stott as the P&M's vicious nemesis and Cumming as the wildly camp Rochester, who manages to give even the so-so dialogue a classy touch."[10]

Despite being panned by the critics, it was acclaimed by worldwide audiences and has gained a cult following.[6][11]

• Plunkett & Macleane at IMDb
• Plunkett & Macleane at Box Office Mojo