32. Colonel Homer
Season 3, Episode 20
Homer makes the transition from suburban corporate cog to managing Springfield's hottest new country music talent, Lurleen Lumpkin. To fully integrate himself into his new position as superstar manager, Homer starts wearing a white cowboy suit that he probably had custom made by Nudie Cohn. Bolo tie, rhinestones, and fringing on the jacket are all essential pieces to this get-up, and Homer makes it work.