| Director | Jake Scott |
|---|---|
| Genre | action film, comedy film |
| Runtime | 96 min |
| Country | United Kingdom, United States |
| Budget | $8.5 million |
| Box office | £3 million |
1748 England is infested with highwaymen — men such as Will Plunkett, a London-based criminal working with his partner Rob. When Rob is killed by the sadistic Thief Taker General Chance 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, a socialite from the upper echelons of society, who had found himself in debtor's prison. Macleane sees the same ruby as his ticket out of debtors' prison and decides to steal it.
Plunkett ambushes Macleane and forces him to give up the ruby, but when Chance's men discover them, 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. Soon enough, they are the most wanted men in England, much to the growing frustration of Chance.
When Macleane falls for the beautiful Lady Rebecca Gibson, the niece of the powerful Lord Gibson, the Lord Chief Justice, their plans to escape to British North America go awry. The pair part ways after a disastrous attempt to rescue Lady Rebecca from a forced marriage, which leads to Lord Gibson's death at the hands of Chance and the discovery that Macleane has recklessly gambled away all of their profits.
Macleane is eventually captured and tried for Lord Gibson's murder. He denies the charge of murder but confesses to cheating his fellow highwayman and expressing remorse, and is sentenced to death by hanging. As Macleane is brought to and hanged on the Tyburn gallows, Plunkett arrives at the last minute and rescues Macleane, aided by Lady Rebecca and the flamboyant Lord Rochester. After a tense chase through the London sewers that sees Plunkett killing Chance, avenging his old partner, the three escape to freedom.