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Two men from completely different ends of the social spectrum enter into a gentleman's agreement.
It is the 18th Century and Will Plunkett (Robert Carlyle) and Captain James Macleane (Jonny Lee Miller) both decide to rid all the aristocrats of their valuable belongings. With Plunkett's criminal back ground and Macleane's social connections the two form a formidable pair as they become the 'Gentlemen Highwayman'.
However one day they hold up the Lord Chief Justice Gibson's (Michael Gambon) coach where Macleane falls in love with the feisty Lady Rebecca Gibson (Liv Tyler). Unfortunately General Chance (Ken Stott), employed by the Lord Chief Justice, is also in love with Lady Rebecca so pursues them. Yet Plunkett risks all for the chance to sort out an old quarrel with Chance, this inevitably leads all three of them into a spot of bother.