In January 1910, Charlie’s show-biz repertoire was further expanded with “a bunch of new songs and a new spiel” that he performed three times at the City Opera House when an amateur minstrel show came to town. Although he injured his hand working at the paper mill in Great Bend, Charlie continued to rehearse his songs and a monologue about the Pine Plains area, which proved to be a hit of the show. The Watertown Daily Times said, “One of the features not on the program, but which nevertheless called out perhaps a larger share of applause than any other number, was that of Charlie Sherman, Huckleberry Charlie.” Or as the man himself told it, “I made more people laugh than any other two numbers on the program.” » Continue Reading.

Charlie Sherman was in great demand and welcome at just about any event he favored, for attracting a crowd was the key to success, and few folks could attract a crowd like Charlie could. He followed an itinerary that lasted for decades, traveling from fair to fair, selling his wares (sometimes vegetables, berries, peanuts, or soda) and working as a huckster, promoting other vendors and exhibits. Roaming the grounds, he delivered spiels, sang, pontificated on everything from politics to local history, talked about his past, and spouted witty sayings, often in poetic fashion. It was a win-win situation, adding to an event’s atmosphere while putting the spotlight on Charlie — and the more attention he received, the more he liked it.

He was already known far and wide as a beloved eccentric, but — either to maintain his status, or because innate quirkiness guided his impulses — Charlie upped his game in the early 1900s by expanding his wardrobe in unusual ways. Whatever the reason, it played out over time as a roaring success. » Continue Reading.