Having done pirates, now let's cover a few of the lesser known but much beloved highwaymen and outlaws.
Wikipedia: https://en.wikipedia.org/wiki/Highwayman
Notable examples include: Claude Duval, whose memorial reads:
Here lies DuVall: Reder, if male thou art,
Look to thy purse; if female, to thy heart.
Much havoc has he made of both; for all
Men he made to stand, and women he made to fall
The second Conqueror of the Norman race,
Knights to his arm did yield, and ladies to his face.
Old Tyburn’s glory; England’s illustrious Thief,
Du Vall, the ladies' joy; Du Vall, the ladies' grief.
Wiki on Claude Duval: https://en.wikipedia.org/wiki/Claude_Duval
And the aptly named Rufus Goodlove, who seduced the wives of wealthy merchants only to rob their houses.
Find more on the List of Highwaymen at Wikipedia: https://en.wikipedia.org/wiki/List_of_highwaymen
&, since we're on the theme - Outlaws: "Black Bart", noted for his charm and verses occasionally left behind at the scene of the crime:
I've labored long and hard for bread,
For honor, and for riches,
But on my corns too long you've tread,
You fine-haired sons of bitches.