Gunpowder Plot. What was the film, V for Vendetta? Historically inaccurate, so I've heard, but certainly entertaining.
Highwaymen... goes well with the pirate theme. Was surprised to hear that someone did a musical rendition of the Noyes poem by that name. I used to make up my own songs reading that poem when I was about 7. Like pirates, of course, the truth is less pretty. I'm sure there were a few cannibal highwaymen out there as well, to go along with the John Stone types (remember, this guy supposedly fathered the third Governor of the Province of Maryland...).
New England had it's own "Dread Pirate" by the name of Dixy Bull:
June 1631, in present Maine, Plymouth Colony’s trading house on Penobscot Bay (present Fort Madison site near Castine, Maine) is attacked by the French. During the attack, English small vessel captain Dixy Bull, assigned to trade with the tribesmen along the fur-rich coast, is attacked by a French pinnace. His boat is captured and all his trade goods (English knives, trading beads and furs) are confiscated. He returns to Boston fired with revenge, and later assembles a crew of 20 “disreputable” men to start a career as “the Dread Pirate” Dixy Bull, at first in order to recover his losses. He originally intended to take back his goods from the French, but he finds that the English along the coast have much more to take and targets his fellow countrymen instead.
The old west had its share of bad influences too. Supposedly there was a Paula Angel that was hung twice in my father's hometown of Las Vegas, New Mexico sometime in the late 1800s (1880s I think). Someone wrote a poem about her too, really laying it on the judge who ordered her executed, though technically with the rope breaking she was supposed to have gone free. Oddly enough for a town that size, my family and hers were not related.