Young James H. Wilson was clearly precocious, musically talented, and filled with boundless energy. Once he left Nicholasville he was able to enjoy an enriched lifestyle as he ventured from his new home in downtown Cincinnati on East Court Street near Main. Living in Cincinnati was totally unlike life in small-town Kentucky, and to this smart teenager the opportunities must have seemed boundless. The theme song of the popular television sitcom series of the 1970s and ‘80s, The Jeffersons, would have been appropriate for James Wilson and his generation of African Americans as it was for Mr. and Mrs. James Jefferson when they moved from Archie and Edith Bunker's working-class neighborhood to the upper-middle- class lifestyle of Manhattan. Though there are many differences between the historical Wilsons and the fictional Jeffersons, both families were on the move and striving to advance—socially, culturally, and economically:

The Wilsons had not yet become members of the middle-class, but James H. Wilson was about to take his first step up the ladder. It was much more difficult for his mother, who could neither read nor write, and for his sister, who could, but who, as a young black woman, had to contend with both the sexism and racism of late- Victorian America.

By 1900 James had already climbed onto the first step up the socio-economic ladder toward middle-class stature. In that year, this nineteen-year-old African American had his occupation recorded on the U. S. Census as a “musician.” As we shall soon see, it is quite likely that by this time he was earning good money and making a substantial contribution to the family income. In fact, the various types of music he performed also elevated his respect in the public eye—both the minstrel music and the concert band repertoire.