A highway man dresses in his cotton uniform ties his mask as he sees a stage coach approach. He jumps on his horse and pulls out his weapon."Stand and Deliver!" . HE points it into the carriage and says"Your money, or your life!" 

Using the most portrayed version of a highway man, some could look like this and others would just jump at passers by with a sword. Such robbers operated in Great Britain and Ireland from the Elizabethan erauntil the early 19th century. One of the first highwaymen were known in the early 15th century, soon before the eventual end of the middle ages.