Sideshow Bob
Bill Oakley and Josh Weinstein, the showrunners for the seventh and eighth seasons, believed that every season of the show should contain an episode starring Sideshow Bob. However, by the seventh season, Bob had already been the focus of four episodes, and writers were having trouble developing new ways to include him. Weinstein describes Bob's dialogue as difficult to write, due to his unique and refined style of speaking. Despite these challenges, however, creators of "The Simpsons" usually look forward to "Sideshow Bob episodes"; the writers consider them enjoyable to write, and former director Dominic Polcino describes them as "a treat" to work on. In "Black Widower", Sideshow Bob notes that he is a "life-long Republican".