Plunkett and Macleane (1999)

Set in the 18th Century, Plunkett and Macleane is the story of two notorious highwaymen based on real-life characters.

The film opens with Macleane (Jonny Lee Miller) languishing in a debtor’s jail in Knightsbridge. He is accidentally freed by Plunkett (Robert Carlyle) in the course of a far-fetched robbery. Both men end up in prison at Newgate, and must buy their way out with a ruby Plunkett has thoughtfully swallowed.

With Plunkett’s brains and know-how and Macleane’s social connections, they infiltrate wealthy society. After robbing the rich they line their pockets – for Plunkett to fulfil his dream of travelling to America and for Macleane to sustain his high cost of living.

When they hold up the coach of the Lord Chief Justice Gibson (Michael Gambon), Macleane falls in love with his beautiful and rebellious niece, Rebecca (Liv Tyler) and his charming manner quickly earns him the nickname “The Gentleman Highwayman”.

Gibson’s second-in-command, Thief-Taker General Chance (Ken Scott), also pursues Rebecca in vain – but it is his relentless pursuit of The Gentleman Highwayman that edges Plunkett and Macleane nearer to capture and possible execution at the famous ‘Tyburn Tree’.

As danger approaches, the partners’ daring and loyalty are pushed to the limit.

Finally, in a botched but noble attempt to save Lady Rebecca, Macleane is captured. In the movie, Plunkett rides up at the last minute to save him. In real life, that did not happen and James Maclaine (the accepted spelling) swung at Tyburn on 3 October 1750 and was buried two days later.

The film gets one thing right: William Plunket was never apprehended.

Plunkett
Robert Carlyle
Macleane
Jonny Lee Miller
Highwayman Rob
Iain Robertson
Thief-Taker General Chance
Ken Stott
Lady Rebecca Gibson
Liv Tyler
Lord Chief Justice Gibson 
Michael Gambon
Eddie
Tommy Flanagan
Dennis
Stephen Walters
Catchpole
James Thornton
Harrison
Terence Rigby
Lord Pelham
Christian Camargo
Liz
Neve McIntosh
Sir Oswald
Matt Lucas
Viscount Bilston
David Walliams
Lord Rochester
Alan Cumming
Lord Ketch
David Foxxe
Winterburn
Alexander Armstrong
Dixon
Ben Miller
Newgate Priest
Karel Polisenský 

Director
Jake Scott