Gilmore Girls season five, episode four, "Tippecanoe and Taylor, Too" (2004) centers on Jackson Belleville challenging Taylor Doose for town selectman after a dispute over zoning regulations, while Rory and Dean face severe relationship hurdles. Jackson wins in a landslide, yet immediately struggles with the bureaucratic demands of the role, marking a shift in Stars Hollow leadership. Read a detailed recap at Gilmore Girls Wiki .
'Gilmore Girls' Season 5, Episode 4: Tippecanoe and Taylor, Too
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