I had the pleasure to meet the winners of the 2024 Madison All-City Spelling Bee and to share some thoughts on English spelling at a recent event with the Madison Rotary Club. We cannot understand English spelling if we believe that it is mainly about matching 44 sounds to 26 letters. I enjoyed illustrating how grammar, history, politics, language contact, and, yes, human error are contributing to the joys and vexations tied to the English spelling system. The 5 words mentioned in the title were sign (spelling ties words of the sign family, including signify and designate, together), name (spelling reflects pronunciation before the Great Vowel Shift), too (spelling differentiates high frequency homophones), isle (spelling reflexed what people believed to be the etymology) and masheen (spelling reflects reform efforts, which, alas, did not come through in this case).