Holbrooke was fascinated by the writings of Edgar Allan Poe which deal with the supernatural and the macabre, eventually producing over thirty compositions which he referred to as his "Poeana". These included orchestral works ("The Raven", "Ulalume", "The Sleeper", "Amontillado" and "The Pit and the Pendulum"), a double concerto for clarinet and bassoon ("Tamerlane"), choral works (a choral symphony "Homage to E.A. Poe" and a poem for chorus and orchestra "The Bells"), a ballet ("The Masque of the Red Death"), a multitude of chamber works (such as the Clarinet Quintet "Ligeia", the Trio "Fairyland" and the Nonet "Irene") and several piano pieces.