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In the late 1890s, Benson was a central figure in the founding the first of the regional companies associated with the North American Phonograph Company called the Chicago Central Phonograph Company, along with Alfred O. Tate and Thomas Lombard.
Several of their wax cylinders survive, most recorded by the North American Phonograph Company, and are among the earliest extant recordings of any African-American musicians, along with recordings by George W. Johnson and a single surviving cylinder recorded by Louis Vasnier.