Actors Michael York and Oliver Reed had previously appeared in the two 1970s swashbuckler movies The Three Musketeers (1973) and The Four Musketeers: Milady's Revenge (1974). In the same year that The Lady and the Highwayman (1989) debuted, the pair appeared in those movies' sequel The Return of the Musketeers (1989).
This name of this tele-film's lead central female character, Barbara Castlemaine (Emma Samms), was similar to the name of the tele-movie's source authoress Barbara Cartland.