The large ensemble arrangements of this artist can be breezy, insidious, shimmering, glitzy, bitsy, and ritzy. Robert Freedman, just as likely to be credited on assignment as a Bob, developed an aesthetic sensibility in which the solid '50s big band jazz sound takes a sharp right-hand curve prior to arrival in the so-called new thing town of Freeville. The conductor wakes up, having driven into a solid wall of velvet cushions. Some new passengers are in the backseat, pop singers such as Billy Joel and Carly Simon, expressing a desire to digest in whole Freedman's arrangements for Grover Washington, Jr., as if they were trays of tiramisu.
Freedman developed early instrumental skills on several reed instruments as well as the piano keyboard vital to any arranger. As a young man he had the benefit of skilled jazz guides such as baritone saxophonist Serge Chaloff and bandleader Woody Herman. By the late '50s he was in the circle of trumpeter Maynard Ferguson and eager to create an academic stronghold for the technical issues at stake in mainstream jazz. Freedman became an instructor in composition and arrangement at the Berklee School, meanwhile setting an example in consistently varied studio projects.