The fan group Watchers of CIS was initially established in 1993, the first year of the broadcast of Highlander: The Series. The "Watchers" in the group's name was a reference to the series' "Watchers", a shadowy organization that exists to observe and monitor the activities of the various Immortals living around the world. "CIS" stands for 'CompuServe Information Systems' - a proprietary online service (the first to offer Internet connectivity, starting in 1989) that provided access to e-mail and online forums before the advent of HTML-coded websites.

Samantha Lynn is the founder of Woodhull and Desmoulins Press, in Harrison Township, MI. She became a Highlander fan during the show's second season, and joined the Watchers as a way of touching base with other fans. Though the Watchers themselves existed before Lynn's membership, the existence of an organized Highlander fandom was still small and unfocused enough that Lynn can be considered one of the founding generation. Lynn grew concerned with the ephemeral nature of the various online conversations on the CIS and other boards, and she offered to begin 'clipping' the more substantive or entertaining discussions and posting them into a newsletter for the group's archives to preserve the discussions and provide new fans with background information. Lynn gave the newsletter the title The Prize.

The Watchers of CIS lasted throughout the run of the original series (1993-1998), but as proprietary services such as CIS became increasingly eclipsed by the development of independent and personal websites, group members began to scatter towards these methods of Internet communication. This, together with the series' cancellation in 1998, signaled the end of the Watchers of CIS, which broke up soon after the end of the series' run.

The Highlander media franchise is comprised of the original film, Highlander, released in 1986, together with four film sequels, two television series (the first, Highlander: The Series, forms the bulk of fannish interest in the franchise), an animated movie, an animated television series, and numerous novels and comic books. Since the franchise's inception in 1986, it has garnered an intense cult following.

The first film introduced the basic mythology of the Highlander universe. Christopher Lambert played Connor MacLeod, a 16th-century Scottish warrior who discovers that he is an Immortal. Immortals are certain individuals scattered throughout the world and history who, once killed violently, are reborn and live forever. However, Immortals can be killed by decapitation, and the Rules which bind the Immortals oblige them to confront each other and battle to the death. The beheading of an Immortal results in the release of energy called "the Quickening", which is absorbed by the victorious Immortal.

Eventually, so goes the saga's mythos, the few remaining Immortals on Earth will be irresistably drawn together into an event called "the Gathering", at which they will battle until one is left. As the film's famous tagline has it, "There can be only one." The Immortal who ultimately triumphs wins The Prize - that is, ultimate, transcendent knowledge and understanding.

Highlander dealt with Connor's gradual understanding of his Immortal nature, helped along by his teacher/mentor Ramirez, a fellow Immortal played by Sean Connery. Connor trains with Ramirez as a warrior, but his wife's death from old age (though Connor, of course, has not aged) embitters him and he wanders the world through the subsequent centuries. In 1985 Connor is drawn to the Gathering, which occurs in New York City. The first film ends with Connor's triumph over the evil Immortal The Kurgan and his attainment of the Prize. (At the time, the producers of the movie were not considering the possibility of sequels.)

Though the film did poorly in the United States, it garned enough profits abroad to inspire a sequel, Highlander II: The Quickening, released in 1991. The film was harshly received by critics and viewers alike, but nonetheless another sequel (Highlander III: The Final Dimension) was released in 1994. However, real fannish interest in the franchise began to coalesce with the introduction of a television spinoff of the movie series, Highlander: The Series, which was syndicated from 1993-1998. The series starred Adrian Paul as Duncan MacLeod (a fellow clansman of the movies' hero Connor), an Immortal attempting to live quietly in the present day until he is drawn back into "The Game", that is, the ongoing struggle between Immortals to destroy each other and leave one standing alone. Throughout the series' six seasons, the show varied between Duncan's present-day battles and his adventures in his previous 400 years of Immortal life across the world. The show garnered general critical acclaim, and fans were drawn to both the complex mythos of the show and to Paul's portrayal of Duncan.

The popularity of the series inspired two movie sequels (Highlander: Endgame (2000) and Highlander: The Source (2007)), a brief spinoff television series (Highlander: The Raven, 1998-1999), an Internet-only Flash animation series (The Mythos Chronicles, 2001), an anime film (Highlander: The Search for Vengeance, 2007), and numerous novels and comic books.