George Lyon
George Lyon may have considered himself a highwayman, but it's said that his only successful holdup was of the Liverpool mail coach, for which he and two accomplices were eventually hanged in 1815.
He makes the list, though, for a spectacularly bungled highway-robbery effort. According to local legend, Lyon once tried to hold up a coach that was transporting wages to a coal mine. He had taken his position by the side of the road nice and early to wait for the coach to pass (at least he was a punctual, if incompetent, criminal), but it was pouring that day and the rain soaked the gunpowder in his pistol. When the coach came along, Lyon's pistol wouldn't fire. The driver simply coaxed his horses into a run, drenching Lyon with water as they sped past.