|Mayor Osgood Bob Flopdinger|
He is played by actor Jerome Dempsey.
Mayor Flopdinger is ever the consummate politician, he sees everyone he meets as a potential voter and vote for him. He is always at the ready to make a proclamation or speech to anyone who cares to listen, but he sometimes gets tongue-tied in the delivery and appears distracted. The mayor's arrival and departures at Shining Time Station are always announced by the squealing of tires and the screeching of brakes. The Mayor is devoted to his wife, Twilene, and has a morbid fear of offending the Friends of the Flowering Cactus Ladies Auxiliary. As Mayor, he is a kind and honest political figure, but is occasionally slow to respond to issues, according to Stacy.
In the first season, the Mayor is a serious character, but in later episodes, he becomes a silly, jolly character.
In the third season he ran for re-election and became mayor of Shining Time.
- Season 1 - Too Many Cooks and 'Tis a Gift
- Season 2 - A Dog's Life (mentioned), Stop the Press, He Loves Me, He Loves Me Not, Is Anybody There? and All's Fair
- Season 3 - Becky Makes a Wish, Mr. Conductor's Fourth of July, and The Mayor Runs for Re-Election
- The Family Specials - Once Upon a Time
- It was mentioned that he is married to a woman named Twilene Flopdinger.