About the Artist

The Charles Pillow Octet is a sleek, modern chamber-jazz outfit born after saxophonist/woodwind doubler Charles Pillow heard vocalist Amy Azzara’s swinging take on “September in the Rain” in 2022 and began writing to feature her. Neither big band nor small combo, the octet lets Pillow—an acclaimed arranger and multi-instrumentalist who toured with Frank Sinatra and has worked with Maria Schneider, Wynton Marsalis, Tom Harrell, and more—craft a sound that nods to Marty Paich/Mel Tormé while feeling distinctly contemporary. Pillow’s charts balance lyrical vocals, tight horn voicings, and agile rhythm-section writing, drawing on his deep catalog as a leader (including Electric Miles 2) and decades of studio and Broadway work. Recent sessions and performances spotlight Azzara alongside Eastman-connected collaborators, highlighting the octet’s blend of elegance, swing, and cinematic color.