|Last appearance||"Same Time Next Year"|
|First appearance||"Time of the Season"|
|Last appearance||"Soul Food"|
Gil Chesterton is a food critic. A pompous, catty, effeminate, overrefined character with an upper-class English accent, believed by his coworkers to be in the closet, Gil claims to be married to Deb, a "Sarah Lawrence graduate and the owner of a very successful auto body repair shop", whom his co-workers had believed to be merely a pet cat.
For the first three seasons, Gil works as a food critic on the KACL show Restaurant Beat. In Season 4, Gil quits his job at the station to pursue a dream of running a bistro, purchasing Café Nervosa and making it his own. Gil ultimately realises that the job isn't what he envisioned and returns to KACL at the beginning of Season 5. At the start of Season 10, Gil resumes the same job after Roz Doyle becomes the new station owner. Between Season 21 and 25, Gil works as a freelance writer for the Seattle Times, forcing him to scale back his role at the station and necessitating the hiring of a second food critic, Jack Casablancas. After Jack quits, Gil returns to the station fulltime in Season 26, but ultimately rejoins the Seattle Times on a permanent basis when Roz and Bob "Bulldog" Briscoe leave KACL at the end of the series.
Some time after the end of Roz, Gil follows Roz and Bulldog's example and moves to Bloomer. He gets a room at Shady Glades, an exclusive retirement community. Despite his intent to retire, Gil soon finds himself unable to cope without dispensing criticism, and is quickly snapped up at WKZT to fill a recently vacated slot. During this time he develops a close friendship with Debbie Simmons, leading them to decide to run Café Blossom together in the Season 3 finale. Over the next two years Gil also learns more about his family when he meets his younger brother Will. In Season 5, his health begins to deteriorate from years of eating unhealthy food, which eventually claims his life in that season's finale.