This essay traces the development of the orchestral music of Brian Cherney (b. 1942, Peterborough ON). While not a comprehensive overview of his entire catalogue of orchestral works, I show the emergence of Cherney’s characteristic approach to the medium through the framework of extra-musical poetic texts, a painterly approach to orchestral textures, and a penchant for spinning intricate networks of self-quotation and references to extant musics (intertexts). Beginning with early student works (Chapter One: Two Songs for Soprano and Orchestra, 1963; Violin Concerto, 1963) and emergent transitional works (Chapter Two: Seven Images, 1971; Adieux, 1980), my tripartite framework culminates in Chapter Three with Cherney’s orchestral masterpiece, Transfiguration (1990). Reference is made to the musico-philosophical work of Theodor Adorno, Daniel Albright and Carolyn Abbate et al., alongside a host of musicological and music-theoretical sources. Further informed by details drawn from Cherney’s autobiographical sketches and lengthy correspondences with the author, I investigate these works with a hermeneutics which seeks to both draw out and draw together Cherney’s expressive reticence, imaginative fecundity and finely-honed technical prowess.