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Gary was the owner of Gary's Olde Towne Tavern, which frequently competed in games of sport or pride against Cheers, either for trophy, bragging rights or an act of humiliation.

After the rivalry was established in season 4, beginning in season 6 one episode per year, all but once called "Bar Wars" , featured a contest between the two pubs. The Cheers gang almost invariably lost to Gary, with the exception of season 4's bowling competition, season 7's 'Bloody Mary' contest, season 9's basketball competition, and season 11's Bar Wars finale, in which Harry "The Hat" Gittes tricks Gary into demolishing his own pub for a worthless check.

Gary was played alternately by both Joel Polis and Robert Desiderio.