While studying fine art, he played jazz in local bands around Long Island, New York.

By 1980, Cheshire moved to Brooklyn where he began attending jam sessions at clubs such as the Blue Coronet and Pumpkins.

During this time he had the opportunity play with Harold Mabern, Kenny Barron, Gil Coggins, Dewey Redman, and Louis Hayes.

During this period he recorded his first sides as a leader, which appear on the album Water Street Revival.

As an electric guitarist, Cheshire's interest in amplification led him to design and build guitar amplifiers with original circuits and visual themes.