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The Dixon Hill stories, written in the 1930s, featured at least two bartenders that Dixon Hill often visited to learn of the whereabouts of certain criminals. One was named Rex who ran his own self-named bar and enthralled Lwaxana Troi; another squealed on Nicky the Nose. (TNG: "Manhunt"; Star Trek: First Contact)
In 2268, Cyrano Jones attempted to sell Antarean glow water, Spican flame gems, and tribbles to a bartender on Deep Space K-7. The bartender wisely declined. Unfortunately, his bar became overwhelmed with the tribbles when they bred and multiplied later on. (TOS: "The Trouble with Tribbles"; DS9: "Trials and Tribble-ations")
Quark was the eponymous owner and bartender of Quark's on Terok Nor (and later Deep Space 9) for at least thirteen years in the 2360s and 2370s. Quark operated the bar through the latter years of the Cardassian Occupation of Bajor, the Cardassian withdrawal, Federation administration of the station, and the Dominion War. Other employees of Quark's also tended the bar, including Rom, Broik, and Leeta. (Star Trek: Deep Space Nine) However, Quark disliked the term "barkeep"; Miles O'Brien once called him a "barkeep", much to Quark's irritation. (DS9: "Captive Pursuit")