Richard "Dick" Turpin of Essex, son of the local butcher, decides against becoming his father's apprentice and instead sets out to become "the world's most famous highwayman." He ends up crossing paths with the Essex gang, a small group of highwaymen (and one highwaywoman), and joins in on one of their robberies. During this robbery, he accidentally kills their leader, thereby winning the adoration and loyalty of the rest of the gang, who hated said leader. As the new Benevolent Boss of the Essex gang, Dick sets out to revolutionize the art of being a highwayman... with mixed results.
Provides examples ff:
- Anachronism Stew: The show is set many centuries in the past, but occasional references are made to modern things: for example, Dick is explicitly a vegan despite that term being recent.
- Animorphism: A hag transforms Dick Turpin into a chicken.
- Benevolent Boss: Dick is this to the Essex gang, which they find a refreshing change from Tom King's tyrannical leadership style.
- Cloudcuckoolander: Honesty has shades of this, with his odd way of thinking.
- The Dandy: Dick is very fashion-conscious and is always dressed to impress.
- Gag Echo: In "The Unrobbable Coach", several characters say phrases along the lines of "only an imbecile would rob the unrobbable coach", always specifically using the word "imbecile", when Dick tries to tell them about the unrobbable coach.
- Egg-Laying Male: While transformed into a chicken, Dick Turpin lays eggs (specifically, colorful patterned eggs).
- Hidden Depths: At first, Dick seems more like The Ditz than anything; he's got some odd ideas and is terrible with violence, but he reveals himself after some time to be quite the Guile Hero.
- The Highwayman: The Essex gang, of course. They're not actually that good at it, especially under Dick's new leadership, but they try.
- Insane Troll Logic: Honesty uses this while trying to trace Dick's steps. It works shockingly well.
- Instantly Proven Wrong: In the season finale, Dick decides to wait for a new adventure to present itself. Nell asserts that adventure doesn't just "present itself" and must be sought out... right before a town official enters the pub and announces that a carriage carrying royal crown jewels will be passing by the town.
- In Touch with His Feminine Side: Dick dislikes violence and enjoys knitting.
- Nice Guy: Moose is an all-around sensitive man who cares for his friends.
- Paper-Thin Disguise: Nell disguised herself as "Nicholas" in order to get more work as a highwayman, but despite not doing anything to hide her feminine body, her gangmates are extremely surprised to learn that she's a woman. Honesty still believes she's a man in the season finale.
- Sweet Polly Oliver: Nell went by the name "Nicholas" for some time to avoid sexism and get good work as a criminal, though her disguise was visibly paper-thin.
- To Know Him, I Must Become Him: While searching for Dick Turpin, Honesty puts on Dick's hat and tries to think of what Dick would do in order to trace his steps.
- Women Are Wiser: Subverted with Nell. At the start of the series she comes across as playing the trope straight, as she is the only female member of the Essex gang, probably the most competent bandit of the lot, and seems to be the Only Sane Woman... but it quickly turns out she actually isn't any smarter than the men, she's just better at banditry. Take her out of her comfort zone and she's practically The Ditz.
- Directly parodied in the series finale, when Tommy Silversides takes over the Essex gang and tells Nell that as "the woman," her role in the gang is to stand on the sidelines and roll her eyes at the men's antics.
- We Will Meet Again: In the season finale, Nell's mother declares herself as an enemy of the Essex Gang and threatens to kill them in the future.
