An early hero of big band guitar, Bob Lessey was born in the British West Indies and did most of his recordings in the '30s. His professional career began along with that era, the guitarist plunking chord changes for an orchestra led by trumpeter Tommy Jones, based out of New York City. Lessey was next associated with Bill Brown and the influential Sam Wooding, joined the group of Tiny Bradshaw in 1934, and the following year began an affiliation with Fletcher Henderson. Lessey, along with fellow guitarist Lawrence Lucie, could be said to have begun writing a book about the subtle art of playing an instrument that was basically barely audible in such a large group -- that is if anyone had bothered to write any of it down.
From here Lessey moved to Don Redman & His Orchestra, performing and recording innovative big band arrangements through 1940. The guitarist's distinguished work in these settings can be examined on Redman collections such as the 1994 Doin' What I Please. In the '40s, doing what Lessey pleased seemed to involve playing less music, although the man has apparently never filed his guitar case away permanently. His final full-time job was with Lucky Millinder; after 1941, Lessey began working for the city of New York.