Vintage sepia matte-finish 8 x 10 portrait photo of a young Sinatra holding a smoldering pipe, signed and inscribed in fountain pen “To Lucy - The sound of your name will always bring me beautiful memories - Frank Sinatra.” Lucy was Lucy Fenton, an army nurse from Philadelphia, who received the signature in the 1930s. In September of 1935, Sinatra appeared on the Major Bowes Amateur Hour as part a group called the Hoboken Four. The group won the show's talent contest and toured with Bowes. Sinatra then took a job as a singing waiter and MC at the Rustic Club in Englewood, NJ. In 1939 bandleader and trumpet player Harry James heard Sinatra on the radio. James hired Sinatra and the two recorded together for the first time on July 13, 1939. At the end of the year he left James to join the Tommy Dorsey Orchestra where he rose to fame as a singer. Accompanied by a portrait of Lucy, and a statement of provenance from her son. In very good condition, with several creases, almost all to borders, some scattered light skipping to ink in inscription due to poor ink flow, a few small spots and a vertical crease affecting Sinatra’s hand. The earliest Sinatra photo we have seen! PSA/DNA LOA and R&R COA.