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Gary was the owner of Gary's Old Towne Tavern, which frequently competed in contests against Cheers. After the rivalry was established in Season 4, beginning in season 6 one episode per year—generally called "Bar Wars" -- featured a contest between the two drinking holes for customers. 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 tricked Gary into demolishing Gary's Olde Towne Tavern.

Joel Polis and Robert Desiderio took turns playing Gary.