Will Plunkett (Robert Carlyle) and Captain James Macleane (Jonny Lee Miller), two men from different ends of the social spectrum in eighteenth century England, enter a gentlemen's agreement: They decide to rid the aristocrats of their belongings. With Plunkett's criminal know-how and Macleane's social connections, they team up to be soon known as "The Gentlemen Highwaymen". But when one day these gentlemen hold up Lord Chief Justice Gibson's (Sir Michael Gambon's) coach, Macleane instantly falls in love with his beautiful and cunning niece, Lady Rebecca Gibson (Liv Tyler). Unfortunately, Thief Taker General Chance (Ken Stott), who also is quite fond of Rebecca, is getting closer and closer to getting both: The Gentlemen Highwaymen and Rebecca, who, needless to say, don't want to get any closer to him. But Plunkett still has a thing to sort out with Chance, and his impulsiveness gets all of them in a little trouble.

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