By Jerry Pearce

On June 6, 1988, Frank Sinatra entered the recording facilities at Evergreen Studios in Los Angeles, California, for what should have been a momentous occasion; for the first time in nearly two years, Sinatra was going to be recording some new music with a live orchestra. In this case, Frank had with him some fantastic big band charts newly written (and conducted at this session) by longtime collaborator and orchestrator Billy May. The orchestra was world class, including Sinatra regulars and semi-regulars Bill Miller, Irving Cottler, Emil Richards, as well as notable players like Snooky Young and Jack Sheldon, who would play memorable trumpet solos throughout the first selection recorded that evening, a swinging arrangement of the Victor Young-Ned Washington song “My Foolish Heart.” Other tunes, including “Cry Me A River” and “If Ever I Would Leave You,” were also on the roster. The album that was being planned was tentatively titled “Digital Sinatra,” with a nod to the new technical wonders that were being achieved in modern recording.