In 1950s England, slow-witted Derek Bentley falls in with a group of petty criminals led by Chris Craig, a teenager with a fondness for American gangster films. Chris and Derek's friendship leads to their involvement in the true case which would forever shake England's belief in capital punishment.

Will Plunkett and Captain James Macleane, two men from different ends of the social spectrum in 18th-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 coach, Macleane instantly falls in love with his beautiful and cunning niece, Lady Rebecca Gibson. Unfortunately, Thief Taker General Chance, who also is quite fond of Rebecca, is getting closer and closer to getting both.